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Chemical effects of nuclear transformations and possible formation of unknown derivatives with N-phenylquinazolinium structure

  • Nadezhda E. Shchepina , Viktor V. Avrorin , Gennadii A. Badun , Sergey N. Shurov and Roman V. Shchepin EMAIL logo
Published/Copyright: June 18, 2019

Abstract

Quinazoline derivatives are well known to have a diverse array of therapeutic activities. Unfortunately, “classic” chemical synthesis does not provide an opportunity for the formation of N-phenyl quaternary 1,3-diazinium compounds. A devised nuclear-chemical method of synthesis based on chemical effects of nuclear transformations enables a new way of the direct nitrogen atom phenylation by the nucleogenic (generated by tritium β-decay) phenyl cations in 1,3-diazines, furnishing, based on our prediction, formation of previously unknown derivatives with N-phenyl quaternary quinazolinium scaffold.


Corresponding author: Dr. Roman V. Shchepin, Department of Radiology, Vanderbilt University Institute of Imaging Science (VUIIS), Nashville, TN 37232, USA, Phone: +1-615-322-8359, Fax: +1-615-322-0734; and Department of Chemistry and Applied Biological Sciences, South Dakota School of Mines and Technology, Rapid City, SD 57701, USA, Phone: +1-605-394-1238

References

1. Onium Compounds – Advances in Research and Application. Q. A. Acton (Ed.), Scholarly Editions, Atlanta, Georgia (2013), p. 100.Search in Google Scholar

2. Hirsch, M., Dhara, S., Diesendruck, C. E.: N-arylation of tertiary amines under mild conditions. Org. Lett. 18, 980 (2016).10.1021/acs.orglett.6b00078Search in Google Scholar PubMed

3. Arava, S., Diesendruck, C. E.: Strategies for the synthesis of N-arylammonium salts. Synthesis 49, 3535 (2017).10.1055/s-0036-1588868Search in Google Scholar

4. Aharonovich, S., Gjineci, N., Dekel, D. R., Diesendruck, C. E.: An effective synthesis of N,N-diphenyl carbazolium salts. Synlett 29, 1314 (2018).10.1055/s-0036-1591848Search in Google Scholar

5. Lv, T., Wang, Z., You, J., Lan, J., Gao, G.: Copper-catalyzed direct aryl quaternization of N-substituted imidazoles to form imidazolium salts. J. Org. Chem. 78, 5723 (2013).10.1021/jo400527rSearch in Google Scholar PubMed

6. Li, S., Yang, F., Lv, T., Lan, J., Gao, G., You, J.: Synthesis of unsymmetrical imidazolium salts by direct quaternization of N-substituted imidazoles using arylboronic acids. Chem. Commun. 50, 3941 (2014).10.1039/c4cc00474dSearch in Google Scholar

7. Carson, T. A.: Dissociation of C6H5T following β-decay. J. Chem. Phys. 32, 1234 (1960).10.1063/1.1730880Search in Google Scholar

8. Wexler, S.: Destruction of molecules by nuclear transformations. Science 156, 901 (1967).10.1126/science.156.3777.901Search in Google Scholar PubMed

9. Cacace, F.: Gaseous carbonium ions from the decay of tritiated molecules. In: V. Gold (Ed.), Advances in Physical Organic Chemistry, Academic Press, London, New York (1970).10.1016/S0065-3160(08)60321-4Search in Google Scholar

10. Cacace, F.: Nuclear decay techniques in ion chemistry. Science 250, 392 (1990).10.1126/science.250.4979.392Search in Google Scholar PubMed

11. Nefedov, V. D., Sinotova, E. N., Akulov, G. P., Syreishchikov, V. A.: β-decay as a method for preparing and studying the reactions of free carbonium ions, radicals, and carbenes. Radiokhimiya 10, 600 (1968).Search in Google Scholar

12. Nefedov, V. D., Toropova, M. A., Sinotova, E. N.: Radiochemical methods for the preparation of organic derivatives of the elements. Russ. Chem. Rev. 38, 873 (1969).10.1070/RC1969v038n11ABEH001859Search in Google Scholar

13. Nefedov, V. D., Sinotova, E. N., Toropova, M. A.: Chemical consequences of beta decay in molecular systems. Radiokhimiya 18, 682 (1976).Search in Google Scholar

14. Speranza, M.: Tritium for generation of carbocations. Chem. Rev. 93, 2933 (1993).10.1021/cr00024a010Search in Google Scholar

15. Nefedov, V. D., Toropova, M. A., Avrorin, V. V., Lewis, S. B., Mattson, B.: Ion-molecular reactions of free phenylium ions, generated by tritium β-decay with group V–VII elements. Tetrahedron Lett. 41, 5303 (2000).10.1016/S0040-4039(00)00854-6Search in Google Scholar

16. Shchepina, N. E., Badun, G. A., Nefedov, V. D., Toropova, M. A., Fedoseev, V. M., Avrorin, V. V., Lewis, S. B.: Synthesis of arylhalonium compounds {including (4-methylphenyl) phenylfluoronium} by nuclear-chemical method. Terahedron Lett. 43, 4123 (2002).10.1016/S0040-4039(02)00717-7Search in Google Scholar

17. Shchepina, N. E., Avrorin, V. V., Badun, G. A.: Nuclear-chemical synthesis of 1,4-diazine quaternary salts. Open J. Synth. Theory Appl. 2, 51 (2013).10.4236/ojsta.2013.22006Search in Google Scholar

18. Shchepina, N. E., Avrorin, V. V., Badun, G. A., Vasyanin, A. N., Shurov, S. N., Agafonova, I. M.: Investigation of ion-molecular reactions of nucleogenic phenyl cations with 1,4-diazine derivatives. Chem. Heterocycl. Compd. 50, 1595 (2015).10.1007/s10593-014-1629-6Search in Google Scholar

19. Michael, J. P.: Quinoline, quinazoline and acridone alkaloids. Nat. Prod. Rep. 25, 166 (2008).10.1039/B612168NSearch in Google Scholar PubMed

20. Mhaske, S. B., Argade, N. P.: The chemistry of recently isolated naturally occurring quinazolinone alkaloids. Tetrahedron 62, 9787 (2006).10.1016/j.tet.2006.07.098Search in Google Scholar

21. Nepali, K., Sharma, S., Ojha, R., Dhar, K.: Vasicine and structurally related quinazolines. Med. Chem. Res. 22, 1 (2013).10.1007/s00044-012-0002-5Search in Google Scholar

22. Suresha, G. P., Prakasha, K. C., Shiva Kumara, K. N., Kapfo, W., Channe Gowda, D.: Design and synthesis of heterocyclic conjugated peptides as novel antimicrobial agents. Int. J. Pept. Res. Ther. 15, 25 (2009).10.1007/s10989-008-9158-8Search in Google Scholar

23. Antipenko, L., Karpenko, A., Kovalenko, S., Katsev, A., Komarovska-Porokhnyavets, E., Novikov, V., Chekotilo, A.: Synthesis of new 2-thio-[1.2,4]triazolo[1,5-c]quinazoline derivatives and its antimicrobial activity. Chem. Pharm. Bull. 57, 580 (2009).10.1248/cpb.57.580Search in Google Scholar PubMed

24. Rohini, R., Shanker, K., Reddy, P. M., Ho, Y. P., Ravinder, V.: Mono and bis-6-arylbenzimidazo[1,2-c]quinazolines: a new class of antimicrobial agents. Eur. J. Med. Chem. 44, 3330 (2009).10.1016/j.ejmech.2009.03.022Search in Google Scholar PubMed

25. Chevalier, J., Mahamoud, A., Baitiche, M., Adam, E., Viveiros, M., Sharandache, A., Militaru, A., Pascu, M. L., Amaral, L., Pages, J.-M.: Quinazoline derivatives are efficient chemosensitizers of antibiotic activity in Enterobacter aerogenes, Klebsiella pneumoniae and Pseudomonas aeruginosa resistant stains. Int. J. Antimicrob. Agents 36, 164 (2010).10.1016/j.ijantimicag.2010.03.027Search in Google Scholar PubMed

26. Myangar, K., Raval, J.: Design, synthesis, and in vitro antimicrobial activities of novel azetidinyl-3-quinazolin-4-one hybrids. Med. Chem. Res. 21, 2762 (2012).10.1007/s00044-011-9808-9Search in Google Scholar

27. Berest, G. G., Voskoboynik, O. Y., Kovalenko, S. I., Nosulenko, I. S., Antypenko, L. M., Antypenko, O. M., Shvets, V. M., Katsev, A. M.: Synthesis of new 6-{[ω-(dialkylamino(heterocyclic)alkyl]thio}-3-R-2H-[1,2,4]triazino[2,3-c]quinazoline-2-ones and evaluation of their anticancer and antimicrobial activities. Sci. Pharm. 80, 37 (2012).10.3797/scipharm.1111-15Search in Google Scholar PubMed PubMed Central

28. Vashi, R. T., Shelat, C. D., Patel, H.: Synthesis and antifungal activity of quinazoline-4-one derivatives containing 8-hydroxy quinazoline ligand and its transition metal chelates. Der Pharma Chem. 2, 216 (2010).Search in Google Scholar

29. Mohamed, M. S., Kamel, M. M., Kassem, E. M. M., Abotaleb, N., Abd El-moez, S. I., Ahmed, M. F.: Novel 6,8-dibromo-4(3H)quinazolinone derivatives of antibacterial and antifungal activities. Eur. J. Med. Chem. 45, 3311 (2010).10.1016/j.ejmech.2010.04.014Search in Google Scholar PubMed

30. Almerico, A. M., Tutone, M., Guarcello, A., Lauria, A.: In vitro and silico studies of polycondensed diazine systems as anti-parasitic agents. Bioorg. Med. Chem. Lett. 22, 1000 (2012).10.1016/j.bmcl.2011.12.004Search in Google Scholar PubMed

31. Selvam, P., Breitenbach, J. M., Borysko, K. Z., Drach, J. C.: Synthesis, antiviral activity, and cytotoxicity of some novel 2-phenyl-3disubstituted quinazolin-4(3H)-ones. Int. J. Drug Des Discov. 1, 149 (2010).10.1016/j.antiviral.2009.02.128Search in Google Scholar

32. Madapa, S., Tusi, Z., Mishra, A., Srivastava, K., Pandey, S. K., Tripathi, R., Puri, S. K., Batra, S.: Search for new pharmacophores for antimalarial activity. Part II: synthesis and antimalarial activity of new 6-ureido-4-anilinoquinazolines. Bioorg. Med. Chem. 17, 222 (2009).10.1016/j.bmc.2008.11.005Search in Google Scholar PubMed

33. Meyynathan, S. N., Ramu, M., Suresh, B.: Synthesis, antimalarial and antibacterial activities of 3-amino acid- and aryl aminosubstituted 2-methyl-3Hquinazolin-4-ones. Med. Chem. Res. 19, 993 (2010).10.1007/s00044-009-9245-1Search in Google Scholar

34. Kashaw, S. K., Kashaw, V., Mishra, P., Jain, N. K., Stables, J. P.: Synthesis, anticonvulsant and CNS depressant activity of some new bioactive 1-(4-substituted-phenyl)-3(4-oxo-2-phenyl/ethyl-4H-quinazolin-3-yl)-urea. Eur. J. Med. Chem. 44, 4335 (2009).10.1016/j.ejmech.2009.05.008Search in Google Scholar PubMed

35. Raghavendra, N. M., Thampi, P., Gurubasavarajaswamy, P. M., Sriram, D.: Synthesis, antitubercular and anticancer activities of substituted furyl-quinazolin-3(4H)-ones. Arch. Pharm. 340, 635 (2007).10.1002/ardp.200700096Search in Google Scholar PubMed

36. Patil, A., Ganguly, S., Surana, S.: Synthesis and antiulcer activity of 2-[5-substituted-1-H-benzo (d) imidazol-2-yl sulfinyl]methyl-3-substituted quinazoline-4-(3H) ones. J. Chem. Sci. 122, 443 (2010).10.1007/s12039-010-0052-5Search in Google Scholar

37. Elansary, A., Kadry, H., Ahmed, E., Sonousi, A.: Design, synthesis and in vitro PDE4 inhibition activity of certain quinazolinone derivatives for treatment of asthma. Med. Chem. Res. 21, 3327 (2012).10.1007/s00044-011-9846-3Search in Google Scholar

38. Kumar, A., Rajput, C. S., Bhati, S. K.: Synthesis of 3-[40-(p-chloro-phenyl)-thiazol-20-yl]-2-[(substituted azetidinone/thiazolidinone)-aminomethyl]-6-bromoquinazolin-4-ones as anti-inflammatory agent. Bioorg. Med. Chem. 15, 3089 (2007).10.1016/j.bmc.2007.01.042Search in Google Scholar PubMed

39. Alafeefy, A. M., Kadi, A. A., El-Azab, A. S., Abdel-Hamide, S. G., Dada, M.-H. Y.: Synthesis, analgesic and anti-inflammatory evaluation of some new 3H-quinazolin-4-one derivatives. Arch. Pharm. 341, 377 (2008).10.1002/ardp.200700271Search in Google Scholar PubMed

40. Hemalatha, K., Girija, K.: Synthesis of some novel 2,3-disubstituted quinazolinones derivatives as analgesic and anti-inflammatory agents. Int. J. Pharm. Pharm. Sci. 3, 103 (2011).Search in Google Scholar

41. Al-Amiery, A., Kadhum, A., Shamel, M., Satar, M., Khalid, Y., Mohamad, A.: Antioxidant and antimicrobial activities of novel quinazolinones. Med. Chem. Res. 23, 236 (2014).10.1007/s00044-013-0625-1Search in Google Scholar

42. Birhan, Y., Bekhit, A., Hymete, A.: Synthesis and antileishmanial evaluation of some 2,3-disubstituted-4(3H)-quinazolinone derivatives. Org. Med. Chem. Lett. 4, 10 (2014).10.1186/s13588-014-0010-1Search in Google Scholar PubMed PubMed Central

43. Liu, G., Yang, S., Song, B., Xue, W., Hu, D., Jin, L., Lu, P.: Microwave assisted synthesis of N-arylheterocyclic substituted-4-aminoquinazoline derivatives. Molecules 11, 272 (2006).10.3390/11040272Search in Google Scholar PubMed PubMed Central

44. Kundu, K., Mahindarathe, M. P. D., Quintero, M. V., Bao, A., Negrete, G. R.: One-pot reductive cyclization to antitumor quinazoline precursors. ARKIVOC 2, 33 (2008).10.3998/ark.5550190.0009.205Search in Google Scholar

45. Zhang, Y., Chen, Z., Lou, Y., Yu, Y.: 2,3-Disubstituted 8-arylamino-3H-imidazo[4,5-g] quinazolines: a novel class of antitumor agents. Eur. J. Med. Chem. 44, 448 (2009).10.1016/j.ejmech.2008.01.009Search in Google Scholar PubMed

46. Castellano, S., Taliani, S., Milite, C., Pugliesi, I., Da Pozzo, E., Rizzetto, E., Bendinelli, S., Costa, B., Cosconati, S., Greco, G., Novellino, E., Sbardella, G., Stefancich, G., Martini, C., Da Settimo, F.: Synthesis and biological evaluation of 4-phenylquinazoline-2-carboxamides designed as a novel class of potent ligands of the translocator protein. J. Med. Chem. 55, 4506 (2012).10.1021/jm201703kSearch in Google Scholar PubMed

47. Selvam, T. P., Kumar, P. V.: Quinazoline marketed drugs – a review. Res. Pharm. 1, 1 (2011).Search in Google Scholar

48. Wang, D., Gao, F.: Quinazoline derivatives: synthesis and bioactivities. Chem. Cent. J. 7, 95 (2013).10.1186/1752-153X-7-95Search in Google Scholar PubMed PubMed Central

49. Fleita, D., Mohareb, R., Sakka, O.: Antitumor and antileishmanial evaluation of novel heterocycles derived from quinazoline scaffold: a molecular modeling approach. Med. Chem. Res. 22, 2207 (2013).10.1007/s00044-012-0213-9Search in Google Scholar

50. Buha, V., Rana, D., Chhabria, M., Chikhalia, K., Mahajan, B., Brahmkshatriya, P., Shah, N.: Synthesis, biological evaluation and QSAR study of series of substituted quinazolines as antimicrobial agents. Med. Chem. Res. 22, 4096 (2013).10.1007/s00044-012-0408-0Search in Google Scholar

51. Anand, R., Narasimhan, B., Chandran, R., Jayaveera, K.: 7-Chloro-3-(substituted benzylidene/phenyl ethylidene amino)-2-phenylquinazolin-4(3H)-ones: synthesis, antimicrobial and antitubercular evaluation. Med. Chem. Res. 22, 2831 (2013).10.1007/s00044-011-9813-zSearch in Google Scholar

52. Malik, S., Khan, S.: Design and evaluation of new hybrid pharmacophore quinazolino-tetrazoles as anticonvulsant strategy. Med. Chem. Res. 23, 207 (2014).10.1007/s00044-013-0630-4Search in Google Scholar

53. Zemlak, K., Szczepankiewicz, W., Kula, B., Bieg, T.: Synthesis of 4-arylaminoquinazolines from 2-amino-N′-arylbenzamidines and orthoesters via the Dimroth rearrangement of intermediate quinazolin-4(3H)-imines. Curr. Org. Chem. 22, 2801 (2018).10.2174/1385272823666181126112958Search in Google Scholar

54. Kaur, N.: Ionic liquids: a versatile medium for the synthesis of six-membered two nitrogen-containing heterocycles. Curr. Org. Chem. 23, 76 (2019).10.2174/1385272823666190111152917Search in Google Scholar

55. Shchepina, N. E., Avrorin, V. V., Badun, G. A., Lewis, S. B., Ukhanov, S. E.: Preparation of fused N-phenyl-substituted pyridinium derivatives by direct phenylation with nucleogenic phenyl cations. Chem. Heterocycl. Compd. 48, 301 (2012).10.1007/s10593-012-0990-6Search in Google Scholar

56. Pilyugin, G. T., Krainer, Z. Y.: Phenylsubstituted quinocyanines. Dokl. Akad. Nauk SSSR 8, 609 (1951).Search in Google Scholar

57. Stadniichuk, N. F., Pilyugin, G. T., Petrenko, O. E.: Reaction of 1-phenylquinolinium salts with Grignard reagent. Zhurnal Obshchei Khimii 40, 1834 (1970).Search in Google Scholar

58. Shchepina, N. E., Avrorin, V. V., Badun, G. A., Alexandrova, G. A., Ukhanov, S. E., Fedoseev, V. M., Lewis, S. B., Boiko, I. I.: Preparation of N-phenyl-substituted quinolinium derivatives labeled with tritium by chemonuclear synthesis. Chem. Heterocycl. Compd. 45, 796 (2009).10.1007/s10593-009-0359-7Search in Google Scholar

59. Schmidt, M. S., Baldridge, K. K., Boatz, J. A., Elbert, S. T., Godron, M. S., Jensen, J. H., Koseki, S., Matsunaga, N., Nguyen, K. A., Su, S. J., Widus, T. L., Dupuis, M., Montgomery, J. A.: General atomic and molecular electronic structure system. J. Comput. Chem. 14, 1347 (1993).10.1002/jcc.540141112Search in Google Scholar

60. Granovsky, A. A. Firefly. Version 8.0.0. http://classic.chem.msu.su/gran/gamess/index.html.Search in Google Scholar

61. Gilchrist, T. L.: Heterocyclic Chemistry, 3rd ed., Longman, New York (1997).Search in Google Scholar

62. Friestad, G. K., Branchaud, B. P.: Tetrafluoroboric acid. In: Encyclopedia of Reagents for Organic Synthesis, John Wiley & Sons, New York (2001).10.1002/047084289X.rt035Search in Google Scholar

63. Jauregui-Osoro, M., Sunassee, K., Weeks, A. J., Berry, D. J., Paul, R. L., Cleij, M., Banga, J. P., O’Doherty, M. J., Marsden, P. K., Clarke, S. E. M., Ballinger, J. R., Szanda, I., Cheng, S.-Y., Blower, P. J.: Synthesis and biological evaluation of [18F]tetrafluoroborate: a PET imaging agent for thyroid disease and reporter gene imaging of the sodium/iodide symporter. Eur. J. Nucl. Med. Mol. Imaging 37, 2108 (2010).10.1007/s00259-010-1523-0Search in Google Scholar PubMed PubMed Central

64. Armarego, W. L. F.: Quinazolines. In: A. R. Katritzky, A. J. Boulton (Eds.), Advances in Heterocyclic Chemistry, Academic Press, New York (1981).Search in Google Scholar

65. Bunting, J. W., Meathrel, W. G.: Quaternization of quinazoline with methyl iodide. Can. J. Chem. 48, 3449 (1970).10.1139/v70-576Search in Google Scholar

66. Albert, A., Goldacre, R., Phillips, J.: The strength of heterocyclic bases. J. Chem. Soc. (Resumed) 2240 (1948).10.1039/jr9480002240Search in Google Scholar

Received: 2018-04-14
Accepted: 2019-05-22
Published Online: 2019-06-18
Published in Print: 2020-01-28

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