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Recent development of imidazole derivatives as potential anticancer agents

  • Naresh Kumar und Nidhi Goel EMAIL logo
Veröffentlicht/Copyright: 13. Januar 2022
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Abstract

Cancer, one of the key health problems globally, is a group of related diseases that share a number of characteristics primarily the uncontrolled growth and invasive to surrounding tissues. Chemotherapy is one of the ways for the treatment of cancer which uses one or more anticancer agents as per chemotherapy regimen. Limitations of most anticancer drugs due to a variety of reasons such as serious side effects, drug resistance, lack of sensitivity and efficacy etc. generate the necessity towards the designing of novel anticancer lead molecules. In this regard, the synthesis of biologically active heterocyclic molecules is an appealing research area. Among heterocyclic compounds, nitrogen containing heterocyclic molecules has fascinated tremendous consideration due to broad range of pharmaceutical activity. Imidazoles, extensively present in natural products as well as synthetic molecules, have two nitrogen atoms, and are five membered heterocyclic rings. Because of their countless physiological and pharmacological characteristics, medicinal chemists are enthused to design and synthesize new imidazole derivatives with improved pharmacodynamic and pharmacokinetic properties. The aim of this present chapter is to discuss the synthesis, chemistry, pharmacological activity, and scope of imidazole-based molecules in anticancer drug development. Finally, we have discussed the current challenges and future perspectives of imidazole-based derivatives in anticancer drug development.


Corresponding author: Nidhi Goel, Department of Chemistry, Institute of Science, Banaras Hindu University, Varanasi, Uttar Pradesh 221005, India, E-mail:

Acknowledgments

Authors are thankful to BHU and IIT Indore for research environment. N.K. acknowledges UGC, India for postdoctoral fellowship.

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: N.G gratefully acknowledges the financial support from UGC, New Delhi (Letter No. F.30-431/2018(BSR), M-14-55) and IoE, BHU (Letter No. R/Dev/D/IoE/Seed Grant/2020-21).

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

References

1. Adjiri, A. DNA mutations may not be the cause of cancer. Oncol Ther 2017;5:85–101. https://doi.org/10.1007/s40487-017-0047-1.Suche in Google Scholar PubMed PubMed Central

2. Ahmad, M. Study on cytochrome P-450 dependent retinoic acid metabolism and its inhibitors as potential agents for cancer therapy. Sci Pharm 2011;79:921–35. https://doi.org/10.3797/scipharm.1106-18.Suche in Google Scholar PubMed PubMed Central

3. Akira, S, Nishio, Y, Inoue, M, Wang, XJ, Wei, S, Matsusaka, T, et al.. Molecular cloning of APRF, a novel IFN-stimulated gene factor 3 p91-related transcription factor involved in the gp130-mediated signaling pathway. Cell 1994;77:63–71. https://doi.org/10.1016/0092-8674(94)90235-6.Suche in Google Scholar PubMed

4. Al-blewi, F, Shaikh, SA, Naqvi, A, Aljohani, F, Aouad, MR, Ihmaid, S, et al.. Design and synthesis of novel imidazole derivatives possessing triazole pharmacophore with potent anticancer activity, and in silico ADMET with GSK-3β molecular docking investigations. Int J Mol Sci 2021;22:1162. https://doi.org/10.3390/ijms22031162.Suche in Google Scholar PubMed PubMed Central

5. Ali, EMH, Abdel-Maksoud, MS, Ammar, UM, Mersal, KI, Ho Yoo, K, Jooryeong, P, et al.. Design, synthesis, and biological evaluation of novel imidazole derivatives possessing terminal sulphonamides as potential BRAFV600E inhibitors. Bioorg Chem 2021;106:104508. https://doi.org/10.1016/j.bioorg.2020.104508.Suche in Google Scholar PubMed

6. Ali, I, Lone, MN, Aboul-Enein, HY. Imidazoles as potential anticancer agents. Med Chem Commun 2017;8:1742–73. https://doi.org/10.1039/c7md00067g.Suche in Google Scholar PubMed PubMed Central

7. Alkahtani, HM, Abbas, AY, Wang, S. Synthesis and biological evaluation of benzo[d]imidazole derivatives as potential anti-cancer agents. Bioorg Med Chem Lett 2012;22:1317–21. https://doi.org/10.1016/j.bmcl.2011.12.088.Suche in Google Scholar PubMed

8. Amada, H, Sekiguchi, Y, Ono, N, Koami, T, Takayama, T, Yabuuchi, T, et al.. 5-(1,3-Benzothiazol-6-yl)-4-(4-methyl-1,3-thiazol-2-yl)-1H-imidazole derivatives as potent and selective transforming growth factor- b type I receptor inhibitors. Bioorg Med Chem 2012;20:7128–38. https://doi.org/10.1016/j.bmc.2012.09.066.Suche in Google Scholar PubMed

9. Amada, H, Sekiguchi, Y, Ono, N, Matsunaga, Y, Koami, T, Asanuma, H, et al.. Design, synthesis, and evaluation of novel 4-thiazolylimidazoles as inhibitors of transforming growth factor-b type 1 receptor kinase. Bioorg Med Chem Lett 2012;22:2024–9. https://doi.org/10.1016/j.bmcl.2012.01.066.Suche in Google Scholar PubMed

10. Andoh, T. DNA topoisomerases in cancer therapy: present and future. Berlin, Germany: Springer Science & Business Media; 2003.10.1007/978-1-4615-0141-1Suche in Google Scholar

11. Armstrong, JL, Ruiz, M, Boddy, AV, Redfern, CP, Pearson, AD, Veal, GJ. Increasing the intracellular availability of all-trans retinoic acid in neuroblastoma cells. Br J Cancer 2005;92:696–704. https://doi.org/10.1038/sj.bjc.6602398.Suche in Google Scholar PubMed PubMed Central

12. Arora, A, Kumari, A, Arora, AA, Nithish, C, Singh, Y. Recent advances made on anticancer drugs–the therapeutic potential of the aromatic heterocyclic compounds. Int J Pharm Sci Rev Res 2019;58:104–13.Suche in Google Scholar

13. Arunkumar, SS. Imidazole and its derivatives and importance in the synthesis of pharmaceuticals: a review. Res J Chem Sci 2015;5:67–72.Suche in Google Scholar

14. Asoh, K, Kohchi, M, Hyoudoh, I, Ohtsuka, T, Masubuchi, M, Kawasaki, K, et al.. Synthesis and structure-activity relationships of novel benzofuran farnesyltransferase inhibitors. Bioorg Med Chem Lett 2009;19:1753–7. https://doi.org/10.1016/j.bmcl.2009.01.074.Suche in Google Scholar PubMed

15. Bai, RL, Pettit, GR, Hamel, E. Binding of dolastatin 10 to tubulin at a distinct site for peptide antimitotic agents near the exchangeable nucleotide and vinca alkaloid sites. J Biol Chem 1990;265:17141–9. https://doi.org/10.1016/s0021-9258(17)44880-0.Suche in Google Scholar

16. Baines, AT, Xu, D, Der, CJ. Inhibition of Ras for cancer treatment: the search continues. Future Med Chem 2011;3:1787–808. https://doi.org/10.4155/fmc.11.121.Suche in Google Scholar PubMed PubMed Central

17. Balderas-Renteria, I, Gonzalez-Barranco, P, Garcia, A, Banik, BK, Rivera, G. Anticancer drug design using scaffolds of β-lactams, sulfonamides, quinoline, quinoxaline and natural products. Drugs advances in clinical trials. Curr Med Chem 2012;19:4377–98. https://doi.org/10.2174/092986712803251593.Suche in Google Scholar PubMed

18. Basso, AD, Kirschmeier, P, Bishop, WR. Lipid posttranslational modifications. Farnesyl transferase inhibitors. J Lipid Res 2006;47:15–31. https://doi.org/10.1194/jlr.r500012-jlr200.Suche in Google Scholar

19. Bates, D, Eastman, A. Microtubule destabilising agents: far more than just antimitotic anticancer drugs. Br J Clin Pharmacol 2017;83:255–68. https://doi.org/10.1111/bcp.13126.Suche in Google Scholar PubMed PubMed Central

20. Baviskar, AT, Madaan, C, Preet, R, Mohapatra, P, Jain, V, Agarwal, A, et al.. N-fused imidazoles as novel anticancer agents that inhibit catalytic activity of topoisomerase IIα and induce apoptosis in G1/S phase. J Med Chem 2011;54:5013–30. https://doi.org/10.1021/jm200235u.Suche in Google Scholar PubMed

21. Benincori, T, Brenna, E, Sannicolo, F. Studies on Wallach’s imidazole synthesis. J Chem Soc, Perkin Trans 1993;6:675–9. https://doi.org/10.1039/p19930000675.Suche in Google Scholar

22. Bennett, MJ, Chan, GK, Rattner, JB, Schriemer, DC. Low-dose laulimalide represents a novel molecular probe for investigating microtubule organization. Cell Cycle 2012;11:3045–54. https://doi.org/10.4161/cc.21411.Suche in Google Scholar PubMed PubMed Central

23. Beretta, GL, Zuco, V, Perego, P, Zaffaroni, N. Targeting DNA topoisomerase I with non-camptothecin poisons. Curr Med Chem 2012;19:1238–57. https://doi.org/10.2174/092986712799320529.Suche in Google Scholar PubMed

24. Bhatnagar, A, Sharma, PK, Kumar, N. A review on “Imidazoles”: their chemistry and pharmacological potentials. Int J PharmTech Res 2011;3:268–82.Suche in Google Scholar

25. Bierie, B, Moses, HL. Tumour microenvironment: TGF-β: the molecular Jekyll and Hyde of cancer. Nat Rev Cancer 2006;6:506–20. https://doi.org/10.1038/nrc1926.Suche in Google Scholar PubMed

26. Blackadar, CB. Historical review of the causes of cancer. World J Clin Oncol 2016;7:54–86. https://doi.org/10.5306/wjco.v7.i1.54.Suche in Google Scholar PubMed PubMed Central

27. Bollag, DM, Mcqueney, PA, Zhu, JZ, Hensens, O, Woods, CM. Epothilones, a new class of microtubule-stabilizing agents with a taxol-like mechanism of action. Cancer Res 1995;55:2325–33.Suche in Google Scholar

28. Bray, F, Ferlay, J, Soerjomataram, I, Siegel, RL, Torre, LA, Jemal, A. Global cancer statistics 2018: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries. CA Cancer J Clin 2018;68:394–424. https://doi.org/10.3322/caac.21492.Suche in Google Scholar PubMed

29. Brendel, E, Ludwig, M, Lathia, C, Robert, C, Ropert, S, Soria, JC, et al.. Pharmacokinetic results of a phase I trial of sorafenib in combination with dacarbazine in patients with advanced solid tumors. Cancer Chemother Pharmacol 2011;68:53–61. https://doi.org/10.1007/s00280-010-1423-9.Suche in Google Scholar PubMed PubMed Central

30. Buchel, GE, Stepanenko, IN, Hejl, M, Jakupec, MA, Keppler, BK, Arion, VB. En route to osmium analogues of KP1019: synthesis, structure, spectroscopic properties and antiproliferative activity of trans-[OsIVCl4(Hazole)2. Inorg Chem 2011;50:7690–7. https://doi.org/10.1021/ic200728b.Suche in Google Scholar PubMed PubMed Central

31. Caraglia, M, De Rosa, G, Salzano, G, Santini, D, Lamberti, M, Sperlongano, P, et al.. Nanotech revolution for the anti-cancer drug delivery through blood-brain-barrier. Curr Cancer Drug Targets 2012;12:186–96. https://doi.org/10.2174/156800912799277421.Suche in Google Scholar PubMed

32. Carlson, RO. New tubulin targeting agents currently in clinical development. Expert Opin Investig Drugs 2008;17:707–22. https://doi.org/10.1517/13543784.17.5.707.Suche in Google Scholar PubMed

33. Chen, J, Ahn, S, Wang, J, Lu, Y, Dalton, JT, Miller, DD, et al.. Discovery of novel 2-aryl-4-benzoyl-imidazole (ABI-III) analogues targeting tubulin polymerization as antiproliferative agents. J Med Chem 2012;55:7285–9. https://doi.org/10.1021/jm300564b.Suche in Google Scholar PubMed PubMed Central

34. Chen, J, Wang, Z, Li, CM, Lu, Y, Vaddady, PK, Meibohm, B, et al.. Discovery of novel 2-aryl-4-benzoyl-imidazoles targeting the colchicines binding site in tubulin as potential anticancer agents. J Med Chem 2010;53:7414–27. https://doi.org/10.1021/jm100884b.Suche in Google Scholar PubMed PubMed Central

35. Chen, J, Wang, Z, Lu, Y, Dalton, JT, Miller, DD, Li, W. Synthesis and antiproliferative activity of imidazole and imidazoline analogs for melanoma. Bioorg Med Chem Lett 2008;18:3183–7. https://doi.org/10.1016/j.bmcl.2008.04.073.Suche in Google Scholar PubMed PubMed Central

36. Chen, JC, Chen, LM, Liao, SY, Zheng, KC, Ji, LN. A DFT study on the hydrolysis mechanism of the potential antitumor Ru(III) complex TzNAMI. THEOCHEM-J Mol Struct 2009;901:137–44. https://doi.org/10.1016/j.theochem.2009.01.011.Suche in Google Scholar

37. Chen, SB, Tan, JH, Ou, TM, Huang, SL, An, LK, Luo, HB, et al.. Pharmacophore based discovery of triaryl-substituted imidazole as new telomeric G-quadruplex ligand. Bioorg Med Chem Lett 2011;21:1004–9. https://doi.org/10.1016/j.bmcl.2010.12.019.Suche in Google Scholar PubMed

38. Christen, D, Griffiths, JH, Sheridan, J. The microwave spectrum of imidazole; complete structure and the electron distribution from nuclear quadrupole coupling tensors and dipole moment orientation. Z Naturforsch A 1981;36:1378–85. https://doi.org/10.1515/zna-1981-1220.Suche in Google Scholar

39. Chun, YJ, Kim, S. Discovery of cytochrome P450 1B1 inhibitors as new promising anti-cancer agents. Med Res Rev 2003;23:657–68. https://doi.org/10.1002/med.10050.Suche in Google Scholar PubMed

40. Ciayadi, R, PotdarM, Walton, KL, Harrison, CA, Kelso, GF, Harris, SJ, et al.. 2-Phenyl and 2-heterocyclic-4-(3-(pyridin-2-yl)-1H-pyrazol-4-yl)pyridines as inhibitors of TGF-b1 and activin A signaling. Bioorg Med Chem Lett 2011;21:5642–5. https://doi.org/10.1016/j.bmcl.2010.12.120.Suche in Google Scholar PubMed

41. Cinelli, MA, Morrell, AE, Dexheimer, TS, Agama, K, Agrawal, S, Pommier, Y, et al.. The structure–activity relationships of A-ring-substituted aromathecin topoisomerase I inhibitors strongly support a camptothecin-like binding mode. Bioorg Med Chem 2010;18:5535–52. https://doi.org/10.1016/j.bmc.2010.06.040.Suche in Google Scholar PubMed PubMed Central

42. Clive, AO, Jones, HE, Bhatnagar, R, Preston, NJ, Maskell, N. Interventions for the management of malignant pleural effusions: a network meta-analysis. Cochrane Database Syst Rev 2016;2016:CD010529. https://doi.org/10.1002/14651858.CD010529.pub2.Suche in Google Scholar PubMed PubMed Central

43. Cragg, GM, Grothaus, PG, Newman, DJ. Impact of natural products on developing new anti-cancer agents. Chem Rev 2009;109:3012–43. https://doi.org/10.1021/cr900019j.Suche in Google Scholar PubMed

44. Das, SS, Alkahtani, S, Bharadwaj, P, Ansari, MT, ALKahtani, MDF, Pang, Z, et al.. Molecular insights and novel approaches for targeting tumor metastasis. Int J Pharm 2020 585:119556. https://doi.org/10.1016/j.ijpharm.2020.119556.Suche in Google Scholar PubMed

45. Dave, H, Shah, M, Trivedi, S, Shukla, S. Prognostic utility of circulating transforming growth factor beta 1 in breast cancer patients. Int J Biol Markers 2012;27:53–9. https://doi.org/10.5301/jbm.2011.8736.Suche in Google Scholar PubMed

46. De Coster, R, Wouters, W, Van Ginckel, R, End, D, Krekels, M, Coene, MC, et al.. Experimental studies with liarozole (R 75, 251): an antitumoral agent which inhibits retinoic acid breakdown. J Steroid Biochem Mol Biol 1992;43:197–201. https://doi.org/10.1016/0960-0760(92)90208-z.Suche in Google Scholar PubMed

47. De Rycker, M, Rigoreau, L, Dowding, S, Parker, PJ. A high-content, cell-based screen identifies micropolyin, a new inhibitor of microtubule dynamics. Chem Biol Drug Des 2009;73:599–610. https://doi.org/10.1111/j.1747-0285.2009.00817.x.Suche in Google Scholar PubMed

48. Debus, H. On the action of ammonia on glyoxal. Ann Chem Pharm 1858;107:199–208. https://doi.org/10.1002/jlac.18581070209.Suche in Google Scholar

49. Derynck, R, Zhang, YE. Smad-dependent and Smad-independent pathways in TGF-beta family signalling. Nature 2003;425:577–84. https://doi.org/10.1038/nature02006.Suche in Google Scholar PubMed

50. Dewang, PM, Kim, DK. Synthesis and biological evaluation of 2-pyridyl-substituted pyrazoles and imidazoles as transforming growth factor-b type 1 receptor kinase inhibitors. Bioorg Med Chem Lett 2010;20:4228–32. https://doi.org/10.1016/j.bmcl.2010.05.032.Suche in Google Scholar PubMed

51. Du, L, Feng, T, Zhao, BY, Li, DH, Cai, SX, Zhu, TJ, et al.. Alkaloids from a deep ocean sediment-derived fungus Penicillium sp. and their antitumor activities. J Antibiot 2010;63:165–70. https://doi.org/10.1038/ja.2010.11.Suche in Google Scholar PubMed

52. Duez, S, Coudray, L, Mouray, E, Grellier, P, Dubois, J. Towards the synthesis of bisubstrate inhibitors of protein farnesyltransferase: synthesis and biological evaluation of new farnesylpyrophosphate analogues. Bioorg Med Chem 2010;18:543–56. https://doi.org/10.1016/j.bmc.2009.12.017.Suche in Google Scholar PubMed

53. Dumontet, C, Jordan, MA. Microtubule-binding agents: a dynamic field of cancer therapeutics. Nat Rev Drug Discov 2010;9:790–803. https://doi.org/10.1038/nrd3253.Suche in Google Scholar PubMed PubMed Central

54. El-Damasy, AK, Haque, MM, Park, JW, Shin, SC, Lee, JS, EunKyeong Kim, E, et al.. 2-Anilinoquinoline based arylamides as broad spectrum anticancer agents with B-RAFV600E/C-RAF kinase inhibitory effects: design, synthesis, in vitro cell-based and oncogenic kinase assessments. Eur J Med Chem 2020;208:112756. https://doi.org/10.1016/j.ejmech.2020.112756.Suche in Google Scholar PubMed

55. Ermolat’ev, DS, Savaliya, B, Shah, A, Van der Eycken, E. One-pot microwave-assisted protocol for the synthesis of substituted 2-amino-1H-imidazoles. Mol Divers 2011;15:491–6. https://doi.org/10.1007/s11030-010-9270-5.Suche in Google Scholar PubMed

56. Fernandez, S, Giglio, J, Rey, AM, Cerecetto, H. Influence of ligand denticity on the properties of novel 99mTc(I)-carbonyl complexes. Application to the development of radiopharmaceuticals for imaging hypoxic tissue. Bioorg Med Chem 2012;20:4040–8. https://doi.org/10.1016/j.bmc.2012.05.010.Suche in Google Scholar PubMed

57. Fletcher, S, Keaney, EP, Cummings, CG, Blaskovich, MA, Hast, MA Glenn, MP, et al.. Structure based design and synthesis of potent, ethylenediamine-based, mammalian farnesyltransferase inhibitors as anticancer agents. J Med Chem 2010;53:6867–88. https://doi.org/10.1021/jm1001748.Suche in Google Scholar PubMed PubMed Central

58. Frank, PV, Girish, KS, Kalluraya, B. Solvent-free microwave-assisted synthesis of oxadiazoles containing imidazole moiety. J Chem Sci 2007;119:41–6. https://doi.org/10.1007/s12039-007-0007-7.Suche in Google Scholar

59. Galmarini, CM, Kamath, K, Vanier-Viornery, A, Hervieu, V, Peiller, E, Falette, N, et al.. Drug resistance associated with loss of p53 involves extensive alterations in microtubule composition and dynamics. Br. J. Cancer 2003;88:1793–9. https://doi.org/10.1038/sj.bjc.6600960.Suche in Google Scholar PubMed PubMed Central

60. Gautier, A, Cisnetti, F. Advances in metal-carbene complexes as potent anti-cancer agents. Metallomics 2012;4:23–32. https://doi.org/10.1039/c1mt00123j.Suche in Google Scholar PubMed

61. Geria, AN, Scheinfeld, NS. Talarozole, a selective inhibitor of P450-mediated all-trans retinoic acid for the treatment of psoriasis and acne. Curr Opin Investig Drugs 2008;9:1228–37.Suche in Google Scholar

62. Giodini, A, Kallio, MJ, Wall, NR, Gorbsky, GJ, Tognin, S, Marchisio, PC, et al.. Regulation of microtubule stability and mitotic progression by survivin. Cancer Res 2002;62:2462–7.Suche in Google Scholar

63. Gomaa, MS, Bridgens, CE, Aboraia, AS, Veal, GJ, Redfern, CP, Brancale, A, et al.. Small molecule inhibitors of retinoic acid 4-hydroxylase (CYP26): synthesis and biological evaluation of imidazole methyl 3-(4-(aryl-2-ylamino) phenyl) propanoates. J Med Chem 2011;54:2778–91. https://doi.org/10.1021/jm101583w.Suche in Google Scholar PubMed

64. Gomaa, MS, Bridgens, CE, Veal, GJ, Redfern, CP, Brancale, A, Armstrong, JL, et al.. Synthesis and biological evaluation of 3-(1 H-imidazol-and triazol-1-yl)-2,2-dimethyl-3-[4-(naphthalen-2-ylamino) phenyl] propyl derivatives as small molecule inhibitors of retinoic acid 4-hydroxylase (CYP26). J Med Chem 2011;54:6803–11. https://doi.org/10.1021/jm200695m.Suche in Google Scholar PubMed

65. Gomaa, MS, Lim, AS, Lau, SC, Watts, AM, Illingworth, NA, Bridgens, CE, et al.. Synthesis and CYP26A1 inhibitory activity of novel methyl 3-[4-(arylamino) phenyl]-3-(azole)-2, 2-dimethylpropanoates. Bioorg Med Chem 2012;20:6080–8. https://doi.org/10.1016/j.bmc.2012.08.044.Suche in Google Scholar PubMed

66. Grasso, CS, Wu, YM, Robinson, DR, Cao, X, Dhanasekaran, SM, Khan, AP, et al.. The mutational landscape of lethal castration-resistant prostate cancer. Nature 2012;487:239–43. https://doi.org/10.1038/nature11125.Suche in Google Scholar PubMed PubMed Central

67. Gu, W, Miao, TT, Hua, DW, Jin, XY, Tao, XB, Huang, CB, et al.. Synthesis and in vitro cytotoxic evaluation of new 1H-benzo[d]imidazole derivatives of dehydroabietic acid. Bioorg Med Chem Lett 2017;27:1296–300. https://doi.org/10.1016/j.bmcl.2017.01.028.Suche in Google Scholar PubMed

68. Gudas, LJ, Wagner, JA. Retinoids regulate stem cell differentiation. J Cell Physiol 2011;226:322–30. https://doi.org/10.1002/jcp.22417.Suche in Google Scholar PubMed PubMed Central

69. Guo, C, Zhang, C, Li, X, Li, W, Xu, Z, Bao, L, et al.. Synthesis and biological evaluation of 1,2,4-trisubstituted imidazoles as inhibitors of transforming growth factor-β type I receptor (ALK5). Bioorg Med Chem Lett 2013;23:5850–4. https://doi.org/10.1016/j.bmcl.2013.08.105.Suche in Google Scholar PubMed

70. Hait, WN. Targeted cancer therapeutics. Cancer Res 2009;69:1263–7. https://doi.org/10.1158/0008-5472.can-08-3836.Suche in Google Scholar

71. Herbertz, S, Sawyer, JS, Stauber, AJ, Gueorguieva, I, Driscoll, KE, Estrem, ST, et al.. Clinical development of galunisertib (LY2157299 monohydrate), a small molecule inhibitor of transforming growth factor-beta signaling pathway. Drug Des Devel Ther 2015;9:4479–99. https://doi.org/10.2147/DDDT.S86621.Suche in Google Scholar PubMed PubMed Central

72. Heusden, JV, Ginckel, RV, Bruwiere, H, Moelans, P, Janssen, B, Floren, W, et al.. Inhibition of all-TRANS-retinoic acid metabolism by R116010 induces antitumour activity. Br J Cancer 2002;86:605–11. https://doi.org/10.1038/sj.bjc.6600056.Suche in Google Scholar PubMed PubMed Central

73. Hindi, KM, Panzner, MJ, Tessier, CA, Cannon, CL, Youngs, WJ. The medicinal applications of imidazolium carbene-metal complexes. Chem Rev 2009;109:3859–84. https://doi.org/10.1021/cr800500u.Suche in Google Scholar PubMed PubMed Central

74. Holmgaard, RB, Schaer, DA, Li, Y, Castaneda, SP, Murphy, MY, Xu, X, et al.. Targeting the TGFβ pathway with galunisertib, a TGFβRI small molecule inhibitor, promotes anti-tumor immunity leading to durable, complete responses, as monotherapy and in combination with checkpoint blockade. J Immunother Cancer 2018;6:47. https://doi.org/10.1186/s40425-018-0356-4.Suche in Google Scholar PubMed PubMed Central

75. Hu, Y, Li, N, Zhang, J, Wang, Y, Chen, L, Sun, J. Artemisinin-indole and artemisinin-imidazole hybrids: synthesis, cytotoxic evaluation and reversal effects on multidrug resistance in MCF-7/ADR cells. Bioorg Med Chem Lett 2019;29:1138–42. https://doi.org/10.1016/j.bmcl.2019.02.021.Suche in Google Scholar PubMed

76. Inman, GJ, Nicolás, FJ, Callahan, JF, Harling, JD, Gaster, LM, Reith, AD, et al.. SB-431542 is a potent and specific inhibitor of transforming growth factor-b superfamily type I activin receptor-like kinase (ALK) receptors ALK4, ALK5, and ALK7. J Mol Pharmacol 2002;62:65–74. https://doi.org/10.1124/mol.62.1.65.Suche in Google Scholar PubMed

77. Jemal, A, Bray, F, Center, MM, Ferlay, J, Ward, E, Forman, D. Global cancer statistics. CA Cancer J Clin 2011;61:69–90. https://doi.org/10.3322/caac.20107.Suche in Google Scholar

78. Jeong, A, Suazo, KF, Wood, WG, Distefano, MD, Li, L. Isoprenoids and protein prenylation: implications in the pathogenesis and therapeutic intervention of Alzheimer’s disease. Crit Rev Biochem Mol Biol 2018;53:279–310. https://doi.org/10.1080/10409238.2018.1458070.Suche in Google Scholar

79. Jin, Z. Muscarine, imidazole, oxazole and thiazole alkaloids. Nat Prod Rep 2009;26:382–445. https://doi.org/10.1039/b718045b.Suche in Google Scholar

80. Jordan, A, Hadfield, JA, Lawrence, NJ, McGown, AT. Tubulin as a target for anticancer drugs: agents which interact with the mitotic spindle. Med Res Rev 1998;18:259–96. https://doi.org/10.1002/(sici)1098-1128(199807)18:4<259::aid-med3>3.0.co;2-u.10.1002/(SICI)1098-1128(199807)18:4<259::AID-MED3>3.0.CO;2-USuche in Google Scholar

81. Jordan, MA, Wilson, L. Microtubules as a target for anticancer drugs. Nat Rev Cancer 2004;4:253–65. https://doi.org/10.1038/nrc1317.Suche in Google Scholar

82. Joshi, G, Kumar, R. Anticancer activity of imidazole fused quinoxalines via human topoisomerase inhibition. J Indian Chem Soc 2020;97:1217–25.Suche in Google Scholar

83. Kamal, A, Balakrishna, M, Nayak, VL, Shaik, TB, Faazil, S, Nimbarte, VD. Design and synthesis of imidazo[2,1-b]thiazole-chalcone conjugates: microtubule-destabilizing agents. ChemMedChem 2014;9:2766–2780. https://doi.org/10.1002/cmdc.201402310.Suche in Google Scholar

84. Kamath, K, Jordan, MA. Suppression of microtubule dynamics by epothilone B is associated with mitotic arrest. Cancer Res 2003;63:6026–31.Suche in Google Scholar

85. Kanthou, C, Tozer, GM. Microtubule depolymerizing vascular disrupting agents: novel therapeutic agents for oncology and other pathologies. Int J Exp Pathol 2009;90:284–94. https://doi.org/10.1111/j.1365-2613.2009.00651.x.Suche in Google Scholar

86. Katsumata, N. Docetaxel: an alternative taxane in ovarian cancer. Br. J. Cancer 2003;89:S9–S15. https://doi.org/10.1038/sj.bjc.6601495.Suche in Google Scholar

87. Kawashita, Y, Hayashi, M. Synthesis of heteroaromatic compounds by oxidative aromatization using an activated carbon/molecular oxygen system. Molecules 2009;14:3073–93. https://doi.org/10.3390/molecules14083073.Suche in Google Scholar

88. Kazi, A, Xiang, S, Yang, H, Chen, L, Kennedy, P, Ayaz, M, et al.. Dual farnesyl and geranylgeranyl transferase inhibitor Thwarts mutant KRAS-driven patient-derived pancreatic tumors. Clin Cancer Res 2019;25:5984–96. https://doi.org/10.1158/1078-0432.ccr-18-3399.Suche in Google Scholar

89. Kennedy, DC, James, BR. Synthesis of ruthenium(II)-4,4ʹ-biimidazole complexes and their potential anti-tumour activity. Can J Chem 2010;88:886–92. https://doi.org/10.1139/v10-076.Suche in Google Scholar

90. Kennedy, DC, Patrick, BO, James, BR. Cationic ruthenium(III) maltolato-imidazole complexes—synthesis, characterization, and antiproliferatory activity. Can J Chem 2011;89:948–58. https://doi.org/10.1139/v11-074.Suche in Google Scholar

91. Keter, FK, Darkwa, J. Perspective: The potential of pyrazole-based compounds in medicine. Biometals 2012;25:9–21. https://doi.org/10.1007/s10534-011-9496-4.Suche in Google Scholar PubMed

92. Kim, DK, Jung, SH, Lee, HS, Dewang, PM. Synthesis and biological evaluation of benzenesulfonamide-substituted 4-(6-alkylpyridin-2-yl)-5-(quinoxalin-6-yl)imidazoles as transforming growth factor-b type 1 receptor kinase inhibitors. Eur J Med Chem 2009;44:568–76. https://doi.org/10.1016/j.ejmech.2008.03.024.Suche in Google Scholar PubMed

93. Kim, M, Lee, J, Jung, K, Kim, H, Aman, W, Ryu, JS, et al.. Design, synthesis and biological evaluation of benzyl 2-(1H-imidazole-1-yl) pyrimidine analogues as selective and potent Raf inhibitors. Bioorg Med Chem Lett 2014;24:3600–4. https://doi.org/10.1016/j.bmcl.2014.05.030.Suche in Google Scholar PubMed

94. Kiselev, E, Dexheimer, TS, Pommier, Y, Cushman, M. Design, synthesis, and evaluation of dibenzo[c,h][1,6] naphthyridines as topoisomerase I inhibitors and potential anticancer agents. J Med Chem 2010;53:8716–26. https://doi.org/10.1021/jm101048k.Suche in Google Scholar PubMed PubMed Central

95. Kong, X, Cheng, R, Wang, J, Fang, Y, Hwang, KC. Nanomedicines inhibiting tumor metastasis and recurrence and their clinical applications. Nano Today 2021;36:101004. https://doi.org/10.1016/j.nantod.2020.101004.Suche in Google Scholar

96. Kueh, HY, Mitchison, TJ. Structural plasticity in actin and tubulin polymer dynamics. Science 2009;325:960–3. https://doi.org/10.1126/science.1168823.Suche in Google Scholar PubMed PubMed Central

97. Kumar, N, Gorai, B, Gupta, S, Shiva, Goel, N. Extrapolation of hydroxytyrosol and its analogues as potential anti-inflammatory agents. J Biomol Struct Dyn 2021;39:5588–99. https://doi.org/10.1080/07391102.2020.1792990.Suche in Google Scholar PubMed

98. Kumar, N, Gupta, S, Chand Yadav, T, Pruthi, V, Kumar Varadwaj, P, Goel, N. Extrapolation of phenolic compounds as multi-target agents against cancer and inflammation. J Biomol Struct Dyn 2019;37:2355–69. https://doi.org/10.1080/07391102.2018.1481457.Suche in Google Scholar PubMed

99. Kunz, PC, Kassack, MU, Hamacher, A, Spingler, B. Imidazole-based phosphane gold(I) complexes as potential agents for cancer treatment: synthesis, structural studies and antitumour activity. Dalton Trans 2009;37:7741–7. https://doi.org/10.1039/b902748c.Suche in Google Scholar PubMed

100. LaBarbera, DV, Modzelewska, K, Glazar, AI, Gray, PD, Kaur, M, Liu, T, et al.. The marine alkaloid naamidine A promotes caspase-dependent apoptosis in tumor cells. Anticancer Drugs 2009;20:425–36. https://doi.org/10.1097/cad.0b013e32832ae55f.Suche in Google Scholar PubMed PubMed Central

101. Laping, NJ, Grygielko, E, Mathur, A, Butter, S, Bomberger, J, Tweed, C, et al.. Inhibition of transforming growth factor (TGF)-beta1-induced extracellular matrix with a novel inhibitor of the TGF-beta type I receptor kinase activity: SB-431542. Mol Pharmacol 2002;62:58–64. https://doi.org/10.1124/mol.62.1.58.Suche in Google Scholar PubMed

102. Lee, J, Kim, H, Yu, H, Chung, JY, Oh, CH, Yoo, KH, et al.. Discovery and initial SAR of pyrimidin-4-yl-1H-imidazole derivatives with antiproliferative activity against melanoma cell lines. Bioorg Med Chem Lett 2010;20:1573–7. https://doi.org/10.1016/j.bmcl.2010.01.064.Suche in Google Scholar PubMed

103. Lee, JS, Newman, RA, Lippman, SM, Huber, MH, Minor, T, Raber, MN, et al.. Phase I evaluation of all-trans-retinoic acid in adults with solid tumors. J Clin Oncol 1993;11:959–66. https://doi.org/10.1200/jco.1993.11.5.959.Suche in Google Scholar

104. Levina, A, Mitra, A, Lay, PA. Recent developments in ruthenium anticancer drugs. Metallomics 2009;1:458–70. https://doi.org/10.1039/b904071d.Suche in Google Scholar PubMed

105. Li, CM, Chen, J, Lu, Y, Narayanan, R, Parke, DN, Li, W, et al.. Pharmacokinetic optimization of 4-substituted methoxybenzoylaryl-thiazole and 2-aryl-4-benzoyl-imidazole for improving oral bioavailability. Drug Metab Dispos 2011;39:1833–9. https://doi.org/10.1124/dmd.110.036616.Suche in Google Scholar PubMed PubMed Central

106. Li, L, Jiang, S, Li, X, Liu, Y, Su, J, Chen, J. Recent advances in trimethoxyphenyl (TMP) based tubulin inhibitors targeting the colchicine binding site. Eur J Med Chem 2018;151:482–94. https://doi.org/10.1016/j.ejmech.2018.04.011.Suche in Google Scholar PubMed

107. Li, L, Quan, D, Chen, J, Ding, J, Zhao, J, Lv, L, et al.. Design, synthesis, and biological evaluation of 1-substituted -2-aryl imidazoles targeting tubulin polymerization as potential anticancer agents. Eur J Med Chem 2019;184:111732. https://doi.org/10.1016/j.ejmech.2019.111732.Suche in Google Scholar PubMed

108. Li, Q, Deng, X, Zu, Y, Lv, H, Su, L, Yao, L, et al.. Cytotoxicity and Topo I targeting activity of substituted 10--nitrogenous heterocyclic aromatic group derivatives of SN-38. Eur J Med Chem 2010;45:3200–6. https://doi.org/10.1016/j.ejmech.2010.03.013.Suche in Google Scholar PubMed

109. Li, Q, Lv, H, Zu, Y, Qu, Z, Yao, L, Su, L, et al.. Synthesis and antitumor activity of novel 20s-camptothecin analogues. Bioorg Med Chem Lett 2009;19:513–5. https://doi.org/10.1016/j.bmcl.2008.11.031.Suche in Google Scholar PubMed

110. Li, S, Yi, Y, Wang, Y, Zhang, Z, Beasly, RS. Camptothecin accumulation and variations in Camptotheca. Planta Med 2002;68:1010–6. https://doi.org/10.1055/s-2002-35652.Suche in Google Scholar PubMed

111. Li, WT, Hwang, DR, Song, JS, Chen, CP, Chen, TW, Lin, CH, et al.. Synthesis and biological evaluation of 2-amino-1-thiazolyl imidazoles as orally active anticancer agents. Invest New Drugs 2012;30:164–75. https://doi.org/10.1007/s10637-010-9547-7.Suche in Google Scholar PubMed

112. Li, WT, Hwang, DR, Song, JS, Chen, CP, Chuu, JJ, Hu, CB, et al.. Synthesis and biological activities of 2-amino-1-arylidenamino imidazoles as orally active anticancer agents. J Med Chem 2010;53:2409–17. https://doi.org/10.1021/jm901501s.Suche in Google Scholar PubMed

113. Li, X, He, L, Chen, H, Wu, W, Jiang, H. Copper-catalyzed aerobic C(sp2)–H functionalization for C–N bond formation: synthesis of pyrazoles and indazoles. J Org Chem 2013;78:3636–46. https://doi.org/10.1021/jo400162d.Suche in Google Scholar PubMed

114. Li, X, Wang, L, Long, L, Xiao, J, Hu, Y, Li, S. Synthesis and biological evaluation of 1,2,4-trisubstituted imidazoles and 1,3,5-trisubstituted pyrazoles as inhibitors of transforming growth factor beta type 1 receptor (ALK5). Bioorg Med Chem Lett 2009;19:4868–72. https://doi.org/10.1016/j.bmcl.2009.04.066.Suche in Google Scholar PubMed

115. Li, Y, Zhang, T, Schwartz, SJ, Sun, D. New developments in Hsp90 inhibitors as anti-cancer therapeutics: mechanisms, clinical perspective and more potential. Drug Resist Updat 2009;12:17–27. https://doi.org/10.1016/j.drup.2008.12.002.Suche in Google Scholar PubMed PubMed Central

116. Liu, K, Zhu, HL. Nitroimidazoles as anti-tumor agents. Anticancer Agents Med Chem 2011;11:687–91. https://doi.org/10.2174/187152011796817664.Suche in Google Scholar PubMed

117. Liu, Z, Meray, RK, Grammatopoulos, TN, Fredenburg, RA, Cookson, MR, Liu, Y, et al.. Membrane-associated farnesylated UCH-L1 promotes alpha-synuclein neurotoxicity and is a therapeutic target for Parkinson’s disease. Proc Natl Acad Sci U S A 2009;106:4635–40. https://doi.org/10.1073/pnas.0806474106.Suche in Google Scholar PubMed PubMed Central

118. Liu, ZC, Zhou, CH, Su, XY, Xie, RG. First synthesis of estrogen-imidazolium cyclophanes. Synth Commun 1999;29:2979–83. https://doi.org/10.1080/00397919908086472.Suche in Google Scholar

119. Lu, Y, Chen, J, Wang, J, Li, CM, Ahn, S, Barrett, CM, et al.. Design, synthesis, and biological evaluation of stable colchicine binding site tubulin inhibitors as potential anticancer agents. J Med Chem 2014;57:7355–66. https://doi.org/10.1021/jm500764v.Suche in Google Scholar PubMed PubMed Central

120. Lu, Y, Li, CM, Wang, Z, Chen, J, Mohler, ML, Li, W, et al.. Design, synthesis, and SAR studies of 4-substituted methoxylbenzoyl-arylthiazoles analogues as potent and orally bioavailable anticancer agents. J Med Chem 2011;54:4678–93. https://doi.org/10.1021/jm2003427.Suche in Google Scholar PubMed PubMed Central

121. Lu, Y, Li, CM, Wang, Z, Ross, CR, Chen, J, Dalton, JT, et al.. Discovery of 4-substituted methoxybenzoyl-aryl-thiazole as novel anticancer agents: synthesis, biological evaluation, and structure-activity relationships. J Med Chem 2009;52:1701–11. https://doi.org/10.1021/jm801449a.Suche in Google Scholar PubMed PubMed Central

122. Lu, Y, Wang, Z, Li, CM, Chen, J, Dalton, JT, Li, W, et al.. Synthesis, in vitro structure-activity relationship, and in vivo studies of 2-arylthiazolidine-4-carboxylic acid amides as anticancer agents. Bioorg Med Chem 2010;18:477–95. https://doi.org/10.1016/j.bmc.2009.12.020.Suche in Google Scholar PubMed PubMed Central

123. Luo, MM, Guo, JS, Zhou, CH, Xie, RG. Design and synthesis of imidazolium cyclophane. Heterocycles 1995;41:1421–4.10.3987/COM-94-7019Suche in Google Scholar

124. Lupsori, S, Tarcomnicu, I, Aonofriesei, F, Iovu, M, Putochin, N. J Ber 1922;55:2749.10.1002/cber.19220550851Suche in Google Scholar

125. Ma, L, Zhang, M, Zhao, R, Wang, D, Ma, Y, Li Ai, L. Plant natural products: promising resources for cancer chemoprevention. Molecules 2021;26:933. https://doi.org/10.3390/molecules26040933.Suche in Google Scholar PubMed PubMed Central

126. Maney, T, Wagenbach, M, Wordeman, L. Molecular dissection of the microtubule depolymerizing activity of mitotic centromere-associated kinesin. J Biol Chem 2001;276:34753–8. https://doi.org/10.1074/jbc.m106626200.Suche in Google Scholar PubMed

127. Manocha, P, Wakode, SR, Kaur, A, Anand, K, Kumar, H. A review: imidazole synthesis and its biological activities. Int J Pharm Sci Res 2016;1:12–6.Suche in Google Scholar

128. Manzo, E, van Soest, R, Matainaho, L, Roberge, M, Andersen, RJ. Ceratamines A and B, antimitotic heterocyclic alkaloids isolated from the marine sponge Pseudoceratina sp. collected in Papua New Guinea. Org Lett 2003;5:4591–4. https://doi.org/10.1021/ol035721s.Suche in Google Scholar PubMed

129. McSorley, LC, Daly, AK. Identification of human cytochrome P450 isoforms that contribute to all-transretinoic acid 4-hydroxylation. Biochem Pharmacol 2000;60:517–26. https://doi.org/10.1016/s0006-2952(00)00356-7.Suche in Google Scholar PubMed

130. Miquel, K, Pradines, A, Sun, J, Qian, Y, Hamilton, AD, Sebti, SM, et al.. GGTI-298 induces G0-G1 block and apoptosis whereas FTI-277 causes G2-M enrichment in A549 cells. Cancer Res 1997;57:1846–50.Suche in Google Scholar

131. Mulvihill, MJ, Kan, JL, Beck, P, Bittner, M, Cesario, C, Cooke, A, et al.. Potent and selective [2-imidazol-1-yl-2-(6-alkoxy-naphthalen-2-yl)-1-methyl-ethyl]-dimethyl-amines as retinoic acid metabolic blocking agents (RAMBAs). Bioorg Med Chem Lett 2005;15:1669–73. https://doi.org/10.1016/j.bmcl.2005.01.044.Suche in Google Scholar PubMed

132. Mumtaz, A, Saeed, A, Fatima, N, Dawood, M, Rafique, H, Iqbal, J. Imidazole and its derivatives as potential candidates for drug development. Bang J Pharm 2016;11:756–64. https://doi.org/10.3329/bjp.v11i4.26835.Suche in Google Scholar

133. Nagai, H, Kim, YH. Cancer prevention from the perspective of global cancer burden patterns. J Thorac Dis 2017;9:448–51. https://doi.org/10.21037/jtd.2017.02.75.Suche in Google Scholar PubMed PubMed Central

134. Navarro, M, Higuera-Padilla, AR, Arsenak, M, Taylor, P. Synthesis, characterization, DNA interaction studies and anticancer activity of platinum-clotrimazole complexes. Transit Metal Chem 2009;34:869–75. https://doi.org/10.1007/s11243-009-9276-y.Suche in Google Scholar

135. Ndagi, U, Mhlongo, N, Soliman, ME. Metal complexes in cancer therapy – an update from drug design perspective. Drug Des Devel Ther 2017;11:599–616. https://doi.org/10.2147/dddt.s119488.Suche in Google Scholar

136. Negi, A, Alex, JM, Amrutkar, SM, Baviskar, AT, Joshi, G, Singh, S, et al.. Imine/amide–imidazole conjugates derived from 5-amino-4-cyano-N1-substituted benzyl imidazole: microwave-assisted synthesis and anticancer activity via selective topoisomerase-II-α inhibition. Bioorg Med Chem 2015;23:5654–61. https://doi.org/10.1016/j.bmc.2015.07.020.Suche in Google Scholar PubMed

137. Ni, WX, Man, WL, Yiu, SM, Ho, M, Cheung, MTW, Ko, CC, et al.. Osmium(VI) nitrido complexes bearing azole heterocycles: a new class of antitumor agents. Chem Sci 2012;3:1582–2588. https://doi.org/10.1039/c2sc01031c.Suche in Google Scholar

138. Nitiss, JL. Targeting DNA topoisomerase II in cancer chemotherapy. Nat Rev Cancer 2009;9:338–50. https://doi.org/10.1038/nrc2607.Suche in Google Scholar PubMed PubMed Central

139. Nodwell, M, Pereira, A, Riffell, JL, Zimmerman, C, Patrick, BO, Roberge, M, et al.. Synthetic approaches to the microtubule-stabilizing sponge alkaloid ceratamine A and desbromo analogues. J Org Chem 2009;74:995–1006. https://doi.org/10.1021/jo802322s.Suche in Google Scholar PubMed

140. Noolvi, MN, Patel, HM, Kaur, M. Benzothiazoles: search for anticancer agents. Eur J Med Chem 2012;54:447–62. https://doi.org/10.1016/j.ejmech.2012.05.028.Suche in Google Scholar PubMed

141. Ojima, I, Lichtenthal, B, Lee, S, Wang, C, Wang, X. Taxane anticancer agents: a patent perspective. Expert Opin Ther Pat 2016;26:1–20. https://doi.org/10.1517/13543776.2016.1111872.Suche in Google Scholar PubMed PubMed Central

142. Oskuei, SR, Mirzaei, S, Reza Jafari-Nik, M, Hadizadeh, F, Eisvand, F, Mosaffa, F, et al.. Design, synthesis and biological evaluation of novel imidazole-chalcone derivatives as potential anticancer agents and tubulin polymerization inhibitors. Bioorg Chem 2021;112:104904. https://doi.org/10.1016/j.bioorg.2021.104904.Suche in Google Scholar PubMed

143. Ozkay, Y, Işikdağ, I, Incesu, Z, Akalin, G. Synthesis of 2-substituted-N-[4-(1-methyl-4,5-diphenyl-1Himidazole-2-yl) phenyl]acetamide derivatives and evaluation of their anticancer activity. Eur J Med Chem 2010;45:3320–8. https://doi.org/10.1016/j.ejmech.2010.04.015.Suche in Google Scholar PubMed

144. Ozpolat, B, Mehta, K, Lopez-Berestein, G. Regulation of a highly specific retinoic acid-4-hydroxylase (CYP26A1) enzyme and all-trans-retinoic acid metabolism in human intestinal, liver, endothelial, and acute promyelocytic leukemia cells. Leuk Lymphoma 2005;46:1497–506. https://doi.org/10.1080/10428190500174737.Suche in Google Scholar PubMed

145. Pan, X, Tao, L, Ji, M, Chen, X, Liu, Z. Synthesis and cytotoxicity of novel imidazo[4,5-d]azepine compounds derived from marine natural product ceratamine A. Bioorg Med Chem Lett 2018;28:866–8. https://doi.org/10.1016/j.bmcl.2018.02.004.Suche in Google Scholar PubMed

146. Park, MS, Park, HJ, An, YJ, Choi, JH, Cha, G, Lee, HJ, et al.. Synthesis, biological evaluation and molecular modelling of 2,4-disubstituted-5-(6-alkylpyridin-2-yl)-1H-imidazoles as ALK5 inhibitors. J Enzyme Inhib Med Chem 2020;35:702–12. https://doi.org/10.1080/14756366.2020.1734799.Suche in Google Scholar PubMed PubMed Central

147. Pathan, MY, Paike, VV, Pachmase, PR, More, SP, Ardhapure, SS, Pawar, RP. Microwave-assisted facile synthesis of 2-substituted 2-imidazolines. ARKIVOC 2006;2006:205–10.10.3998/ark.5550190.0007.f25Suche in Google Scholar

148. Patil, S, Deally, A, Gleeson, B, M¨uller-Bunz, H, Paradisi, F, Tacke, M. Synthesis, cytotoxicity and antibacterial studies of symmetrically and non-symmetrically benzyl- or p-cyanobenzyl-substituted N-heterocyclic carbene-silver complexes. Appl Organomet Chem 2010;24:781–93. https://doi.org/10.1002/aoc.1702.Suche in Google Scholar

149. Patil, S, Deally, A, Gleeson, B, M¨uller-Bunz, H, Paradisi, F, Tacke, M. Novel benzyl-substituted N-heterocyclic carbene-silver acetate complexes: synthesis, cytotoxicity and antibacterial studies. Metallomics 2011;3:74–88. https://doi.org/10.1039/c0mt00034e.Suche in Google Scholar PubMed

150. Pautu, V, Lepeltier, E, Mellinger, A, Riou, J, Debuigne, A, Jérôme, C, et al.. pH-Responsive lipid nanocapsules: a promising strategy for improved resistant melanoma cell internalization. Cancers (Basel) 2021;13:2028. https://doi.org/10.3390/cancers13092028.Suche in Google Scholar PubMed PubMed Central

151. Pickup, M, Novitskiy, S, Moses, HL. The roles of TGF-β in the tumour microenvironment. Nat Rev Cancer 2013;13:788–99. https://doi.org/10.1038/nrc3603.Suche in Google Scholar PubMed PubMed Central

152. Pommier, Y. DNA topoisomerase I inhibitors: chemistry, biology, and interfacial inhibition. Chem Rev 2009;109:2894–902. https://doi.org/10.1021/cr900097c.Suche in Google Scholar PubMed PubMed Central

153. Pommier, Y, Cushman, M. The indenoisoquinoline noncamptothecin topoisomerase I inhibitors: update and perspectives. Mol Cancer Ther 2009;8:1008–14. https://doi.org/10.1158/1535-7163.mct-08-0706.Suche in Google Scholar

154. Qasim, SS, Ali, SS. Microwave assisted a novel synthesis for new substituted imidazoles. Der Pharma Chem 2011;3:518–22.Suche in Google Scholar

155. Rademaker-Lakhai, JM, van den Bongard, D, Pluim, D, Beijnen, JH, Schellens, JHM. A phase I and pharmacological study with imidazolium-trans-DMSO-imidazole-tetrachlororuthenate, a novel ruthenium anticancer agent. Clin Cancer Res 2004;10:3717–27. https://doi.org/10.1158/1078-0432.ccr-03-0746.Suche in Google Scholar

156. Rajitha, C, Dubey, P, Sunku, V, Piedrafita, FJ, Veeramaneni, VR, Pal, M. Synthesis and pharmacological evaluations of novel 2H-benzo[b][1,4]oxazin-3(4H)-one derivatives as a new class of anti-cancer agents. Eur J Med Chem 2011;46:4887–96. https://doi.org/10.1016/j.ejmech.2011.07.045.Suche in Google Scholar PubMed

157. Ramurthy, S, Taft, BR, Aversa, RJ, Barsanti, PA, Burger, MT, Lou, Y, et al.. Design and discovery of N-(3-(2-(2-Hydroxyethoxy)-6-morpholinopyridin-4-yl)-4-methylphenyl)-2-(trifluoromethyl)isonicotinamide, a selective, efficacious, and well-tolerated RAF inhibitor targeting RAS mutant cancers: the path to the clinic. J Med Chem 2020;63:2013–27. https://doi.org/10.1021/acs.jmedchem.9b00161.Suche in Google Scholar PubMed

158. Ravera, M, Gabano, E, Sardi, M, Ermondi, G, Caron, G, McGlinchey, MJ, et al.. Synthesis, characterization, structure, molecular modeling studies and biological activity of sterically crowded Pt(II) complexes containing bis(imidazole) ligands. J Inorg Biochem 2011;105:400–9. https://doi.org/10.1016/j.jinorgbio.2010.12.002.Suche in Google Scholar PubMed

159. Ren, Y, Wang, Y, Li, G, Zhang, Z, Ma, L, Cheng, B, et al.. Discovery of novel benzimidazole and indazole analogues as tubulin polymerization inhibitors with potent anticancer activities. J Med Chem 2021;64:4498–515. https://doi.org/10.1021/acs.jmedchem.0c01837.Suche in Google Scholar PubMed

160. Richaud, A, Barba-Behrens, N, Méndez, F. Chemical reactivity of the imidazole: a semblance of pyridine and pyrrole? Org Lett 2011;13:972–5. https://doi.org/10.1021/ol103011h.Suche in Google Scholar PubMed

161. Robert, CE. Heterocyclic compounds. New York: John Wiley & Sons, Inc.; 1957, vol. 5.Suche in Google Scholar

162. Rowinska-Zyrek, M, Witkowska, D, Potocki, S, Remellib, M, Kozlowskia, H. His-rich sequences is plagiarism from nature a good idea? New J Chem 2013;37:58–70. https://doi.org/10.1039/c2nj40558j.Suche in Google Scholar

163. Rowinsky, EK, Windle, JJ, Von Hoff, DD. Ras protein farnesyltransferase: a strategic target for anticancer therapeutic development. J Clin Oncol 1999;17:3631–52. https://doi.org/10.1200/jco.1999.17.11.3631.Suche in Google Scholar PubMed

164. Rudolph, KE, Liberio, MS, Davis, RA, Carroll, AR. Pteridine-, thymidine-, choline- and imidazole derived alkaloids from the Australian ascidian, Leptoclinides durus. Org Biomol Chem 2013;11:261–70. https://doi.org/10.1039/c2ob26879e.Suche in Google Scholar PubMed

165. Sanchez, J, Carter, TR, Cohen, MS, Blagg, BSJ. Old and new approaches to target the Hsp90 chaperone. Curr Cancer Drug Targets 2020;20:253–70. https://doi.org/10.2174/1568009619666191202101330.Suche in Google Scholar PubMed PubMed Central

166. Satam, V, Babu, B, Chavda, S, Savagian, M, Sjoholm, R, Tzou, S, et al.. Novel diamino imidazole and pyrrole-containing polyamides: synthesis and DNA binding studies of mono- and diamino-phenyl-ImPy*Im polyamides designed to target 5ʹ-ACGCGT-3ʹ. Bioorg Med Chem 2012;20:693–701. https://doi.org/10.1016/j.bmc.2011.12.010.Suche in Google Scholar PubMed

167. Sato, S, Iwata, F, Takeo, J, Kawahara, H, Kuramoto, M, Uno, H. Stellettazole D, A cytotoxic imidazole alkaloid from the marine sponge Jaspis duoaster. Chem Lett 2011;40:186–7. https://doi.org/10.1246/cl.2011.186.Suche in Google Scholar

168. Saxer, S, Marestin, C, Mercier, R, Dupuy, J. The multicomponent Debus-Radzizewski reaction in macromolecular chemistry. Polym Chem 2018;9:1927–33. https://doi.org/10.1039/c8py00173a.Suche in Google Scholar

169. Shalini, K, Sharma, PK, Kumar, N. Imidazole and its biological activities: a review. Chem Sin 2010;1:36–47.Suche in Google Scholar

170. Shang, H, Chen, H, Zhao, D, Tang, X, Liu, Y, Pan, L, et al.. Synthesis and biological evaluation of 4α/4β-imidazolyl podophyllotoxin analogues as antitumor agents. Arch Pharm 2012;345:43–8. https://doi.org/10.1002/ardp.201100094.Suche in Google Scholar PubMed

171. Sharbeen, G, McCarroll, J, Liu, J, Youkhana, J, Limbri, LF, Biankin, AV, et al.. Delineating the role of betaiv-tubulins in pancreatic cancer: betaIVb-tubulin inhibition sensitizes pancreatic cancer cells to Vinca alkaloids. Neoplasia 2016;18:753–64. https://doi.org/10.1016/j.neo.2016.10.011.Suche in Google Scholar PubMed PubMed Central

172. Sharma, V, Gupta, M, Kumar, P, Sharma, A. A comprehensive review on fused heterocyclic as DNA intercalators: promising anticancer agents. Curr Pharm Des 2021;27:15–42. https://doi.org/10.2174/1381612826666201118113311.Suche in Google Scholar PubMed

173. Sharma, P, LaRosa, C, Antwi, J, Govindarajan, R, Werbovetz, KA. Imidazoles as potential anticancer agents: an update on recent studies. Molecules 2021;26:4213. https://doi.org/10.3390/molecules26144213.Suche in Google Scholar PubMed PubMed Central

174. Shiota, M, Dejima, T, Yamamoto, Y, Takeuchi, A, Imada, K, Kashiwagi, E, et al.. Collateral resistance to taxanes in enzalutamide-resistant prostate cancer through aberrant androgen receptor and its variants. Cancer Sci 2018;109:3224–34. https://doi.org/10.1111/cas.13751.Suche in Google Scholar PubMed PubMed Central

175. Shrestha, L, Bolaender, A, Patel, HJ, Taldone, T. Heat shock protein (HSP) drug discovery and development: targeting heat shock proteins in disease. Curr Top Med Chem 2016;16:2753–64. https://doi.org/10.2174/1568026616666160413141911.Suche in Google Scholar PubMed PubMed Central

176. Simoni, D, Romagnoli, R, Baruchello, R, Rondanin, R, Rizzi, M, Pavani, MG, et al.. Novel combretastatin analogues endowed with antitumor activity. J Med Chem 2006;49:3143–52. https://doi.org/10.1021/jm0510732.Suche in Google Scholar PubMed

177. Singh, I, Luxami, V, Paul, K. Synthesis of naphthalimide-phenanthro[9,10-d]imidazole derivatives: in vitro evaluation, binding interaction with DNA and topoisomerase inhibition. Bioorg Chem 2020;96:103631. https://doi.org/10.1016/j.bioorg.2020.103631.Suche in Google Scholar PubMed

178. Siwach, A, Verma, PK. Synthesis and therapeutic potential of imidazole containing compounds. BMC Chem 2021;15:12. https://doi.org/10.1186/s13065-020-00730-1.Suche in Google Scholar PubMed PubMed Central

179. Skok, Ž, Zidar, N, Kikelj, D, Ilaš, J. Dual inhibitors of human DNA topoisomerase II and other cancer-related targets. J Med Chem 2020;63:884–904. https://doi.org/10.1021/acs.jmedchem.9b00726.Suche in Google Scholar PubMed

180. Smith, MA, Parkinson, DR, Cheson, BD, Friedman, MA. Retinoids in cancer therapy. J Clin Oncol 1992;10:839–64. https://doi.org/10.1200/jco.1992.10.5.839.Suche in Google Scholar

181. Sondhi, SM, Singh, J, Rani, R, Gupta, PP, Agrawal, SK, Saxena, AK. Synthesis, anti-inflammatory and anticancer activity evaluation of some novel acridine derivatives. Eur J Med Chem 2010;45:555–63. https://doi.org/10.1016/j.ejmech.2009.10.042.Suche in Google Scholar PubMed

182. Song, YL, Shao, ZY, Dexheimer, TS, Scher, ES, Pommier, Y, CushmanM. Structure-based design, synthesis, and biological studies of new anticancer norindenoisoquinoline topoisomerase I inhibitors. J Med Chem 2010;53:1979–89. https://doi.org/10.1021/jm901649x.Suche in Google Scholar PubMed PubMed Central

183. Souza, ET, Castro, LC, Castro, FAV, do Canto Visentin, L, Pinheiro, CB, Pereira, MD, et al.. Synthesis, characterization and biological activities of mononuclear Co(III) complexes as potential bioreductively activated prodrugs. J Inorg Biochem 2009;103:1355–65. https://doi.org/10.1016/j.jinorgbio.2009.07.008.Suche in Google Scholar PubMed

184. Stepanov, AI, Astrat’ev, AA, Sheremetev, AB, Lagutina, NK, Palysaeva, NV, Tyurin, AY, et al.. A facile synthesis and microtubule-destabilizing properties of 4-(1H-benzo [d] imidazol-2-yl)-furazan-3-amines. Eur J Med Chem 2015;94:237–51. https://doi.org/10.1016/j.ejmech.2015.02.051.Suche in Google Scholar PubMed

185. Stoppie, P, Borgers, M, Borghgraef, P, Dillen, L, Goossens, J, Sanz, G, et al.. R115866 inhibits all-trans-retinoic acid metabolism and exerts retinoidal effects in rodents. J Pharmacol Exp Ther 2000;293:304–12.Suche in Google Scholar

186. Su, JC, Chang, CH, Wu, SH, Shiau, CW. Novel imidazopyridine suppresses STAT3 activation by targeting SHP-1. J Enzyme Inhib Med Chem 2018;33:1248–55. https://doi.org/10.1080/14756366.2018.1497019.Suche in Google Scholar PubMed PubMed Central

187. Subia, B, Dahiya, UR, Mishra, S, Ayache, J, Casquillas, GV, Caballero, D, et al.. Breast tumor-on-chip models: from disease modeling to personalized drug screening. J Control Release 2021;331:103–20. https://doi.org/10.1016/j.jconrel.2020.12.057.Suche in Google Scholar PubMed PubMed Central

188. Sun, B, Liu, K, Han, J, Zhao, LY, Su, X, Lin, B, et al.. Design, synthesis, and biological evaluation of amide imidazole derivatives as novel metabolic enzyme CYP26A1 inhibitors. Bioorg Med Chem 2015;23:6763–73. https://doi.org/10.1016/j.bmc.2015.08.019.Suche in Google Scholar PubMed

189. Tabassum, S, Khan, RA, Arjmand, F, Juvekar, AS, Zingde, SM. Synthesis of carbo hydrate-conjugate heterobimetallic CuII–Sn2IV and ZnII–Sn2IV complexes; their interactions with CT DNA and nucleotides; DNA cleavage, in-vitro cytotoxicity. Eur J Med Chem 2010;45:4797–806. https://doi.org/10.1016/j.ejmech.2010.07.046.Suche in Google Scholar PubMed

190. Takle, AK, Brown, MJ, Davies, S, Dean, DK, Francis, G, Gaiba, A, et al.. The identification of potent and selective imidazole-based inhibitors of B-Raf kinase. Bioorg Med Chem Lett 2006;16:378–81. https://doi.org/10.1016/j.bmcl.2005.09.072.Suche in Google Scholar PubMed

191. Tan, C, Hu, S, Liu, J, Ji, LN. Synthesis, characterization, antiproliferative and anti-metastatic properties of two ruthenium DMSO complexes containing 2,2’-biimidazole. Eur J Med Chem 2011;46:1555–63. https://doi.org/10.1016/j.ejmech.2011.01.074.Suche in Google Scholar PubMed

192. Tang, XH, Gudas, LJ. Retinoids, retinoic acid receptors, and cancer. Annu Rev Pathol 2011;6:345–64. https://doi.org/10.1146/annurev-pathol-011110-130303.Suche in Google Scholar PubMed

193. Tang, YD, Zhang, JQ, Zhang, SL, Geng, RX, Zhou, CH. Synthesis and characterization of thiophene derived amido bis-nitrogen mustard and its antimicrobial and anticancer activities. Chin J Chem 2012;30:1831–40. https://doi.org/10.1002/cjoc.201100668.Suche in Google Scholar

194. Tardito, S, Marchio, L. Copper compounds in anticancer strategies. Curr Med Chem 2009;16:1325–48. https://doi.org/10.2174/092986709787846532.Suche in Google Scholar PubMed

195. Uno, T, Kawai, Y, Yamashita, S, Oshiumi, H, Yoshimura, C, Mizutani, T, et al.. Discovery of 3-ethyl-4-(3-isopropyl-4-(4-(1-methyl-1H-pyrazol-4-yl)-1H-imidazol-1-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl)benzamide (TAS-116) as a potent, selective, and orally available HSP90 inhibitor. J Med Chem 2019;62:531–51. https://doi.org/10.1021/acs.jmedchem.8b01085.Suche in Google Scholar PubMed

196. Vanleusen, AM, Wildeman, J, Oldenziel, O. Chemistry of sulfonylmethyl isocyanides. 12. Base-induced cycloaddition of sulfonylmethyl isocyanides to carbon, nitrogen double bonds. Synthesis of 1,5-disubstituted and 1,4,5-trisubstituted imidazoles from aldimines and imidoyl chlorides. J Org Chem 1977;42:1153–9. https://doi.org/10.1021/jo00427a012.Suche in Google Scholar

197. Verfaille, CJ, Thissen, CA, Bovenschen, HJ, Mertens, J, Steijlen, PM, van de Kerkhof, PC. Oral R115866 in the treatment of moderate to severe plaque-type psoriasis. J Eur Acad Dermatol Venereol 2007;21:1038–46. https://doi.org/10.1111/j.1468-3083.2007.02158.x.Suche in Google Scholar PubMed

198. Vincent, TL, Gatenby, RA. An evolutionary model for initiation, promotion, and progression in carcinogenesis. Int J Oncol 2008;32:729–37.10.3892/ijo.32.4.729Suche in Google Scholar

199. Wadas, TJ, Wong, EH, Weisman, GR, Anderson, CJ. Copper chelation chemistry and its role in copper radiopharmaceuticals. Curr Pharm Des 2007;13:3–16. https://doi.org/10.2174/138161207779313768.Suche in Google Scholar PubMed

200. Wan, PT, Garnett, MJ, Roe, SM, Lee, S, Niculescu-Duvaz, D, Good, VM, et al., Cancer Genome Project. Mechanism of activation of the RAF-ERK signaling pathway by oncogenic mutations of B-RAF. Cell 2004;116:855–67. https://doi.org/10.1016/s0092-8674(04)00215-6.Suche in Google Scholar PubMed

201. Wang, J, Yao, X, Huang, J. New tricks for human farnesyltransferase inhibitor: cancer and beyond. Medchemcomm 2017;8:841–54. https://doi.org/10.1039/c7md00030h.Suche in Google Scholar PubMed PubMed Central

202. Wang, Q, Arnst, KE, Wang, Y, Kumar, G, Ma, D, White, SW, et al.. Structure-guided design, synthesis, and biological evaluation of (2-(1H-Indol-3-yl)-1H-imidazol-4-yl)(3,4,5-trimethoxyphenyl) Methanone (ABI-231) analogues targeting the colchicine binding site in tubulin. J Med Chem 2019;62:6734–50. https://doi.org/10.1021/acs.jmedchem.9b00706.Suche in Google Scholar PubMed

203. Wang, X, He, Q, Wu, K, Guo, T, Du, X, Zhang, H, et al.. Design, synthesis and activity of novel 2,6-disubstituted purine derivatives, potential small molecule inhibitors of signal transducer and activator of transcription 3. Eur J Med Chem 2019;179:218–32. https://doi.org/10.1016/j.ejmech.2019.06.017.Suche in Google Scholar PubMed

204. Wang, Y, Zhou, CH. Recent advances in the researches of triazole compounds as medicinal drugs. Sci Sin Chem 2011;41:1429–56. (in Chinese). https://doi.org/10.1360/032010-843.Suche in Google Scholar

205. Weaver, BA. How Taxol/paclitaxel kills cancer cells. Mol Biol Cell 2014;25:2677–81. https://doi.org/10.1091/mbc.e14-04-0916.Suche in Google Scholar PubMed PubMed Central

206. Wei, W, Ayad, NG, Wan, Y, Zhang, GJ, Kirschner, MW, Kaelin, WGJr. Degradation of the SCF component Skp2 in cell-cycle phase G1 by the anaphase-promoting complex. Nature 2004;428:194–8. https://doi.org/10.1038/nature02381.Suche in Google Scholar PubMed

207. Wei, X, Liu, J, Zhang, GL, Jiang, ZL, Zhou, CH, Luo, K, et al.. An effective methodology to novel larger imidazolium cyclophanes. Lett Org Chem 2005;2:507–11. https://doi.org/10.2174/1570178054640804.Suche in Google Scholar

208. Witchard, HM, Watson, KG. Synthesis of 5-amino-3-methylimidazolidine-2,4-dione and 1,3,5-triazine derivatives as analogues of the alkaloids naamidine A and G. Synthesis 2010;2010:4312–6.10.1055/s-0030-1258963Suche in Google Scholar

209. Xiao, Z, Lei, F, Chen, X, Wang, X, Cao, L, Ye, K, et al.. Design, synthesis, and antitumor evaluation of quinoline-imidazole derivatives. Arch Pharm (Weinheim) 2018;351: e1700407. https://doi.org/10.1002/ardp.201700407.Suche in Google Scholar PubMed

210. Xie, HQ, Kang, YJ. Role of copper in angiogenesis and its medicinal implications. Curr Med Chem 2009;16:1304–14. https://doi.org/10.2174/092986709787846622.Suche in Google Scholar PubMed

211. Xu, Y, Zi, Y, Lei, J, Mo, X, Shao, Z, Wu, Y, et al.. pH-Responsive nanoparticles based on cholesterol/imidazole modified oxidized-starch for targeted anticancer drug delivery. Carbohydr Polym 2020;233:115858. https://doi.org/10.1016/j.carbpol.2020.115858.Suche in Google Scholar PubMed

212. Yadav, TC, Srivastava, AK, Dey, A, Kumar, N, Raghuwanshi, N, Pruthi, V. Application of computational techniques to unravel structure-function relationship and their role in therapeutic development. Curr Top Med Chem 2018;18:1769–91. https://doi.org/10.2174/1568026619666181120142141.Suche in Google Scholar PubMed

213. Yang, L, Lin, S, Xu, L, Lin, J, Zhao, C, Huang, X. Novel activators and small-molecule inhibitors of STAT3 in cancer. Cytokine Growth Factor Rev 2019;49:10–22. https://doi.org/10.1016/j.cytogfr.2019.10.005.Suche in Google Scholar PubMed

214. Yang, YQ, Chen, H, Liu, QS, Sun, Y, Gu, W. Synthesis and anticancer evaluation of novel 1H-benzo[d]imidazole derivatives of dehydroabietic acid as PI3Kα inhibitors. Bioorg Chem 2020;100:103845. https://doi.org/10.1016/j.bioorg.2020.103845.Suche in Google Scholar PubMed

215. Yoon, JS, Jarhad, DB, Kim, G, Nayak, A, Zhao, LX, Yu, J, et al.. Design, synthesis and anticancer activity of fluorocyclopentenyl-purines and -pyrimidines. Eur J Med Chem 2018;155:406–17. https://doi.org/10.1016/j.ejmech.2018.06.003.Suche in Google Scholar PubMed

216. Yu, H, Jung, Y, Kim, H, Lee, J, Oh, CH, Yoo, KH, et al.. 1,4-dihydropyrazolo[4,3-d]imidazole phenyl derivatives: a novel type II Raf kinase inhibitors. Bioorg Med Chem Lett 2010;20:3805–8. https://doi.org/10.1016/j.bmcl.2010.04.039.Suche in Google Scholar PubMed

217. Yu, KG, Liu, JC, Zhou, CH, Diao, JL, Xu, T, Li, DH. Synthesis of porphyrin-nitroimidazole derivatives and their radiosensitization. Chin J Med Chem 2008;18:414–9.Suche in Google Scholar

218. Zhang, C, Moran, EJ, Woiwode, TF, Short, KM, Mjalli, AM. Synthesis of tetrasubstituted imidazoles via α-(N-acyl-N-alkylamino)-β-ketoamides on Wang resin. Tetrahedron Lett 1996;37:751–4. https://doi.org/10.1016/0040-4039(95)02310-0.Suche in Google Scholar

219. Zhang, HZ, Damu, GLV, Cai, GX, Zhou, CH. Current developments in the syntheses of 1,2,4-triazole compounds. Curr Org Chem 2014;18:359–406. https://doi.org/10.2174/13852728113179990025.Suche in Google Scholar

220. Zhang, J, Zhang, F, Li, H, Liu, C, Xia, J, Ma, L, et al.. Recent progress and future potential formetal complexes as anticancer drugs targeting G-quadruplex DNA. Curr Med Chem 2012;19:2957–75. https://doi.org/10.2174/092986712800672067.Suche in Google Scholar PubMed

221. Zhang, L, Peng, XM, Damu, GLV, Geng, RX, Zhou, CH. Comprehensive review in current developments of imidazole-based medicinal chemistry. Med Res Rev 2014;34:340–437. https://doi.org/10.1002/med.21290.Suche in Google Scholar PubMed

222. Zhang, S, Zannikos, P, Awada, A, Piccart-Gebhart, M, Dirix, LY, Fumoleau, P, et al.. Pharmacokinetics of tipifarnib after oral and intravenous administration in subjects with advanced cancer. J Clin Pharmacol 2006;46:1116–27. https://doi.org/10.1177/0091270006291034.Suche in Google Scholar PubMed

223. Zhang, WT, Zhou, CH, Ji, QG. 2-chloro-N-[(4-chlorophenyl)(phenyl)-methyl]-N-[2-(4-nitro-1Himidazol-1-yl)-ethyl]ethanamine. Acta Crystallogr Sect E 2011;67(Pt 2):o491. https://doi.org/10.1107/S160053681100256X.Suche in Google Scholar PubMed PubMed Central

224. Zhao, F, Lu, W, Su, F, Xu, L, Jiang, D, Sun, X, et al.. Synthesis and potential antineoplastic activity of dehydroabietylamine imidazole derivatives. Med Chem Commun 2018;9:2091–9. https://doi.org/10.1039/c8md00487k.Suche in Google Scholar PubMed PubMed Central

225. Zhao, F, Wang, W, Lu, W, Xu, L, Yang, S, Cai, XM, et al.. High anticancer potency on tumor cells of dehydroabietylamine Schiff-base derivatives and a copper(II) complex. Eur J Med Chem 2018;146:451–9. https://doi.org/10.1016/j.ejmech.2018.01.041.Suche in Google Scholar PubMed

226. Zhao, G, Lin, H. Metal complexes with aromatic N-containing ligands as potential agents in cancer treatment. Curr Med Chem Anticancer Agents 2005;5:137–47. https://doi.org/10.2174/1568011053174873.Suche in Google Scholar PubMed

227. Zhao, J, Liang, Y, Yin, Q, Liu, S, Wang, Q, Tang, Y, et al.. Clinical and prognostic significance of serum transforming growth factor-beta1 levels in patients with pancreatic ductal adenocarcinoma. Braz J Med Biol Res 2016;49:e5485. https://doi.org/10.1590/1414-431X20165485.Suche in Google Scholar PubMed PubMed Central

228. Zhao, N, Wang, YL, Yang, JY. A rapid and convenient synthesis of derivatives of imidazoles under microwave irradiation. JCCS 2005;52:535–8. https://doi.org/10.1002/jccs.200500078.Suche in Google Scholar

229. Zheng, X, Ma, Z, Zhang, D. Synthesis of imidazole-based medicinal molecules utilizing the van leusen imidazole synthesis. Pharmaceuticals 2020;13:37. https://doi.org/10.3390/ph13030037.Suche in Google Scholar PubMed PubMed Central

230. Zhou, B, Der, CJ, Cox, AD. The role of wild type RAS isoforms in cancer. Semin Cell Dev Biol 2016;58:60–9. https://doi.org/10.1016/j.semcdb.2016.07.012.Suche in Google Scholar PubMed PubMed Central

231. Zhou, CH, Gan, LL, Zhang, YY, Zhang, FF, Wang, GZ, Jin, L, et al.. Review on supermolecules as chemical drugs. Sci China, Ser B 2009;52:415–58. https://doi.org/10.1007/s11426-009-0103-2.Suche in Google Scholar

232. Zhou, CH, Wang, Y. Recent researches in triazole compounds as medicinal drugs. Curr Med Chem 2012;19:239–80. https://doi.org/10.2174/092986712803414213.Suche in Google Scholar PubMed

233. Zhou, CH, Xie, RG, Zhao, HM. Convenient and efficient synthesis of imidazolium cyclophanes. Org Prep Proc Int 1996;28:345–7. https://doi.org/10.1080/00304949609356541.Suche in Google Scholar

234. Zhou, CH, Zhang, FF, Gan, LL, Zhang, YY, Geng, RX. Research in supermolecular chemical drugs. Sci China, Ser B 2009;39:208–52. (in Chinese).Suche in Google Scholar

235. Zhou, CH, Zhang, YY, Yan, CY, Wan, K, Gan, LL, Shi, Y. Recent researches in metal supramolecular complexes as anticancer agents. Anticancer Agents Med Chem 2010;10:371–95. https://doi.org/10.2174/1871520611009050371.Suche in Google Scholar

236. Zhou, J, Giannakakou, P. Targeting microtubules for cancer chemotherapy. Curr Med Chem Anticancer Agents 2005;5:65–71. https://doi.org/10.2174/1568011053352569.Suche in Google Scholar PubMed

237. Zhou, W, Zhang, W, Peng, Y, Jiang, ZH, Zhang, L, Du, Z. Design, synthesis and anti-tumor activity of novel benzimidazole-chalcone hybrids as non-intercalative topoisomerase II catalytic inhibitors. Molecules 2020;25:3180. https://doi.org/10.3390/molecules25143180.Suche in Google Scholar PubMed PubMed Central

238. Zhu, HY, Cooper, AB, Desai, J, Njoroge, G, Kirschmeier, P, Bishop, WR, et al.. Discovery of C-imidazole azaheptapyridine FPT inhibitors. Bioorg Med Chem Lett 2010;20:1134–6. https://doi.org/10.1016/j.bmcl.2009.12.013.Suche in Google Scholar PubMed

239. Zhu, HY, Desai, J, Cooper, AB, James, W, Rane, DE, Kirschmeier, P, et al.. New class of azaheptapyridine FPT inhibitors as potential cancer therapy agents. Bioorg Med Chem Lett 2014;24:1228–31. https://doi.org/10.1016/j.bmcl.2013.12.046.Suche in Google Scholar PubMed

240. Zhu, L, Li, G, Luo, L, Guo, P, Lan, J, You, J. Highly functional group tolerance in copper-catalyzed N-arylation of nitrogen-containing heterocycles under mild conditions. J Org Chem 2009;74:2200–2. https://doi.org/10.1021/jo802669b.Suche in Google Scholar PubMed

241. Zhu, XC, Lu, WT, Zhang, YZ, Reed, A, Newton, B, Fan, Z, et al.. Imidazole modified porphyrin as a pH-responsive sensitizer for cancer photodynamic therapy. Chem Commun 2011;47:10311–3. https://doi.org/10.1039/c1cc13328d.Suche in Google Scholar PubMed

242. Zuliani, V, Cocconcelli, G, Fantini, M, Ghiron, C, Rivara, M. A practical synthesis of 2,4(5)-diarylimidazoles from simple building blocks. J Org Chem 2007;72:4551–3. https://doi.org/10.1021/jo070187d.Suche in Google Scholar PubMed

Published Online: 2022-01-13

© 2021 Walter de Gruyter GmbH, Berlin/Boston

Artikel in diesem Heft

  1. Frontmatter
  2. Reviews
  3. Recent endeavors in microbial remediation of micro- and nanoplastics
  4. Metal nanoparticles and its application on phenolic and heavy metal pollutants
  5. The story of nitrogen
  6. Recent development of imidazole derivatives as potential anticancer agents
  7. Indole based prostate cancer agents
  8. Lawsone (2-hydroxy-1,4-naphthaquinone) derived anticancer agents
  9. Small modular nuclear reactors are mostly bad policy
  10. A holistic environmental investigation of complementary energy in Alberta
  11. Green synthesis of various saturated S-heterocyclic scaffolds: an update
  12. Recent advances of heterocycle based anticancer hybrids
  13. Molecular docking and MD: mimicking the real biological process
  14. Synthesis of quinazolinone and quinazoline derivatives using green chemistry approach
  15. Nuclear fusion: the promise of endless energy
  16. Finance for Green Chemistry through Currency Mix
  17. Synthesis of bioactive scaffolds catalyzed by agro-waste-based solvent medium
  18. Recent developments in the green synthesis of biologically relevant cinnolines and phthalazines
  19. Detection of Rapid Eye Movement Behaviour Sleep Disorder using Time and Frequency Analysis of EEG Signal Applied on C4-A1 Channels
  20. Recent developments in C–C bond formation catalyzed by solid supported palladium: a greener perspective
  21. Visible-light-mediated metal-free C–Si bond formation reactions
  22. An overview of quinoxaline synthesis by green methods: recent reports
  23. Naturally occurring, natural product inspired and synthetic heterocyclic anti-cancer drugs
  24. Synthesis of bioactive natural products and their analogs at room temperature – an update
  25. One-pot multi-component synthesis of diverse bioactive heterocyclic scaffolds involving 6-aminouracil or its N-methyl derivatives as a versatile reagent
  26. Synthesis of new horizons in benzothiazole scaffold and used in anticancer drug development
  27. Triazine based chemical entities for anticancer activity
  28. Modification of kaolinite/muscovite clay for the removal of Pb(II) ions from aqueous media
  29. In silico design of ACE2 mutants for competitive binding of SARS-CoV-2 receptor binding domain with hACE2
  30. Computational study of Cu n AgAu (n = 1–4) clusters invoking DFT based descriptors
  31. Development of an online assessment system to evaluate knowledge on chemical safety and security
  32. Developing a questionnaire for diabetes mellitus type 2 risk effects and precondition factors – multivariate statistical paths
  33. Antioxidant and antibacterial activities of two xanthones derivatives isolated from the leaves extract of Anthocleista schweinfurthii Gilg (Loganiaceae)
  34. The stability increase of α-amylase enzyme from Aspergillus fumigatus using dimethyladipimidate
  35. Sustainability of ameliorative potentials of urea spiked poultry manure biochar types in simulated sodic soils
  36. Cytotoxicity test and antibacterial assay on the compound produced by the isolation and modification of artonin E from Artocarpus kemando Miq.
  37. Effects of alum, soda ash, and carbon dioxide on 40–50 year old concrete wastewater tanks
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