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Synthesis of some chalcones derivatives series and their antituberculosis activity

  • Noviany Noviany EMAIL logo , Hasnah Osman , Suriyati Mohamad , Sutopo Hadi , Heri Satria and Buhani Buhani
Published/Copyright: January 24, 2024
Pure and Applied Chemistry
From the journal Pure and Applied Chemistry Volume 96 Issue 3

Abstract

Chalcone is an important biosynthetic precursor, due to the diverse pharmacological activities. The aim of this current study was to synthesize 14 new chalcone derivatives compounds by incorporating p-alkoxyacetophenones with substituted benzaldehydes. Two new series of chalcone derivatives have been synthesized using the alkylation and the base catalysed Claisen-Schmidt condensation. All the synthesized compounds were fully characterized by IR, 1D NMR (1H and 13C NMR) and 2D NMR (COSY, HMQC, HMBC) as well as mass spectrometry analysis. All the synthesized compounds were assayed in vitro for their antituberculosis activities against Mycobacterium tuberculosis strain. Among them, compounds (E)-1-[4-(heptoxy)phenyl]-3-(2-hydroxy-5-bromophenyl)prop-2-en-1-one (5a), (E)-1-[4-(octyloxy)phenyl]-3-(2-hydroxy-5-bromophenyl)prop-2-en-1-one (5b) and (E)-1-[4-(decyloxy)phenyl]-3-(2-hydroxy-5-bromophenyl)prop-2-en-1-one (5d) showed good activities with the lowest MIC value of 12.5 μg/mL.

Keywords: antituberculosis activity; chalcones derivatives; Mycobacterium tuberculosis ; VCCA–2023
Corresponding author: Noviany Noviany, Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Lampung, Bandar Lampung 35145, Indonesia, e-mail:
Article note: A collection of invited papers based on presentations at the Virtual Conference on Chemistry and its Applications 2023 (VCCA-2023).

Funding source: Universitas Lampung

Award Identifier / Grant number: 778/UN26.21/PN/2022

Funding source: Universitas Lampung HETI

Award Identifier / Grant number: 6047/UN26/HK.01.03/2022-2023

Acknowledgments

I would like to forward my appreciation to the technical and laboratory staffs of USM, Mr. Zahari Othman, Ms. Nabiha and Mr. Thaigarajan Parumasivam for their assistance.

  1. Research funding: The authors thank the Higher Education for Technology and Innovation (HETI) Project Implementation Unit (PIU) University of Lampung with agreement numbers of 6047/UN26/HK.01.03/2022-2023 and PT-BLU University of Lampung with agreement numbers of 778/UN26.21/PN/2022.

References

[1] M. Rudrapal, J. Khan, A. A. B. Dukhyil, R. M. I. I. Alarousy, E. I. Attah, T. Sharma, S. J. Khairnar, A. R. Bendale. Molecules 26, 7177 (2021), https://doi.org/10.3390/molecules26237177.Search in Google Scholar PubMed PubMed Central

[2] M. N. Gomes, E. N. Muratov, M. Pereira, J. C. Peixoto, L. P. Rosseto, P. V. Cravo, C. H. Andrade, B. J. Neves. Molecules 22, 1210 (2017), https://doi.org/10.3390/molecules22081210.Search in Google Scholar PubMed PubMed Central

[3] Y. Tong, Y. Lyu, S. Xu, L. Zhang, J. Zhou. Crit. Rev. Biotechnol. 41, 1194 (2021).10.1080/07388551.2021.1922350Search in Google Scholar PubMed

[4] A. A. E. Nadia, H. Hrichi, R. A. Alolayan, W. Derafa, F. M. Zahou, R. B. Bakr. ACS Omega 7, 2 (2022).Search in Google Scholar

[5] Y. Ouyang, J. Li, X. Chen, X. Fu, S. Sun, Q. Wu. Biomolecules 11(6), 894 (2021), https://doi.org/10.3390/biom11060894.Search in Google Scholar PubMed PubMed Central

[6] M. Čižmáriková, P. Takáč, G. Spengler, A. Kincses, M. Nové, M. Vilková, J. Mojžiš. Anticancer Res. 39(12), 6499 (2019), https://doi.org/10.21873/anticanres.13864.Search in Google Scholar PubMed

[7] H.-L. Qin, Z.-W. Zhang, R. Lekkala, H. Alsulami, K. Rakesh. Eur. J. Med. Chem. 193, 112215 (2020), https://doi.org/10.1016/j.ejmech.2020.112215.Search in Google Scholar PubMed

[8] Y. Fu, D. Liu, H. Zeng, X. Ren, B. Song, D. Hu, X. Gan. RSC Adv. 10(41), 24483 (2020), https://doi.org/10.1039/d0ra03684f.Search in Google Scholar PubMed PubMed Central

[9] M. A. Alsafi, D. L. Hughes, M. A. Said. Acta Crystallogr., Sect. C: Struct. Chem. 76(12), 1043 (2020), https://doi.org/10.1107/s2053229620014217.Search in Google Scholar PubMed

[10] N. Duran, M. F. Polat, D. A. Aktas, M. A. Alagoz, E. Ay, F. Cimen, E. Tek, B. Anil, S. Burmaoglu, O. Algul. Int. J. Clin. Pract. 75, e14846, e14846 (2021).10.1111/ijcp.14846Search in Google Scholar PubMed PubMed Central

[11] R. Kalirajan. Coronaviruses 1, 13 (2020), https://doi.org/10.2174/2666796701999200625210746.Search in Google Scholar

[12] S. W. Kahssay, G. S. Hailu, K. T. Desta. Drug Des. Dev. Ther. 15, 3119 (2021).10.2147/DDDT.S316185Search in Google Scholar PubMed PubMed Central

[13] A. Jain, D. Jain. Int. J. Pharmaceut. Sci. Res. 59, 5700 (2019).Search in Google Scholar

[14] E. N. Okolo, D. I. Ugwu, B. E. Ezema, J. C. Ndefo, F. U. Eze, C. G. Ezema, J. A. Ezugwu, O. T. Ujam. Sci. Rep. 11, 21871 (2021).Search in Google Scholar

[15] E. J. Henry, S. J. Bird, P. Gowland, M. Collins, J. P. Cassella. J. Antibiot. 73(5), 299 (2020), https://doi.org/10.1038/s41429-020-0280-y.Search in Google Scholar PubMed

[16] H. Benouda, B. Bouchal, A. Challioui, A. Oulmidi, T. Harit, F. Malek, A. Riahi, M. Bellaoui, B. Bouammali. Lett. Drug Des. Discov. 16(1), 93 (2018), https://doi.org/10.2174/1570180815666180404130430.Search in Google Scholar

[17] B. Lakshminarayanan, N. Kannappan, T. Subburaju. Int. J. Pharmaceut. Res. Biosci. 11(10), 4974 (2020).Search in Google Scholar

[18] J. Higgs, C. Wasowski, A. Marcos, M. Jukič, C. H. Paván, S. Gobec, F. D. T. Pinto, N. Colettis, M. Marder. Heliyon 5(3), e01376 (2019), https://doi.org/10.1016/j.heliyon.2019.e01376.Search in Google Scholar PubMed PubMed Central

[19] A. N. Choudhary, A. Kumar, V. Juy. Lett. Drug Des. Discov. 9(5), 479 (2012).10.2174/157018012800389368Search in Google Scholar

[20] A. T. Bale, U. Salar, K. M. Khan, S. Chigurupati, T. Fasina, F. Ali, M. Ali, S.S. Nanda, M. Taha, S. Perveen. Lett. Drug Des. Discov. 18(3), 249 (2021), https://doi.org/10.2174/1570180817999201001155032.Search in Google Scholar

[21] N. A. Al Zahrani, R. M. El-Shishtawy, M. M. Elaasser, A. M. Asiri. Molecules 25(19), 4566 (2020), https://doi.org/10.3390/molecules25194566.Search in Google Scholar PubMed PubMed Central

[22] H. ur Rashid, Y. Xu, N. Ahmad, Y. Muhammad, L. Wang. Bioorg. Chem. 87, 335 (2019), https://doi.org/10.1016/j.bioorg.2019.03.033.Search in Google Scholar PubMed

[23] O. Nurkenov, M. Ibraev, I. Schepetkin, A. Khlebnikov, T. Seilkhanov, A. Arinova, M. Isabaeva. Russ. J. Gen. Chem. 89(7), 1360 (2019), https://doi.org/10.1134/s1070363219070028.Search in Google Scholar

[24] T. S. Ibrahim, A. H. Moustafa, A. J. Almalki, R. M. Allam, A. Althagafi, S. Md, M. F. Mohamed. J. Enzyme Inhib. Med. Chem. 36(1), 1067 (2021), https://doi.org/10.1080/14756366.2021.1929201.Search in Google Scholar PubMed PubMed Central

[25] S. Murtaza, K. Z. Mir, A. Tatheer, R. S. Ullah. Lett. Drug Des. Discov. 16(3), 322 (2019), https://doi.org/10.2174/1570180815666180523085436.Search in Google Scholar

[26] N. Fakhrudin, K. K. Pertiwi, M. I. Takubessi, E. F. Susiani, A. Nurrochmad, S. Widyarini, A. Sudarmanto, A. A. Nugroho, S. A. Wahyuono. Pharmacia 67, 173 (2020), https://doi.org/10.3897/pharmacia.67.e56788.Search in Google Scholar

[27] D. O. Escrivani, R. L. Charlton, M. B. Caruso, G. A. Burle-Caldas, M. P. G. Borsodi, R. B. Zingali, N. Arruda-Costa, M. V. PalmeiraMello, J. B. de Jesus, A. M. Souza, B. Abrahim-Vieira, S. Freitag-Pohl, E. Pohl, P. W. Denny, B. Rossi-Bergmann, P. G. Steel. PLoS Neglected Trop. Dis. 15(11), e0009951 (2021), https://doi.org/10.1371/journal.pntd.0009951.Search in Google Scholar PubMed PubMed Central

[28] J. Khan, P. K. Deb, S. Piya, K. D. Medina, R. Devi, S. G. Walode, M. Rudrapal. Molecules 26, 4021 (2021), https://doi.org/10.3390/molecules26134021.Search in Google Scholar PubMed PubMed Central

[29] R. M. Martinez, F. A. Pinho-Ribeiro, V. S. Steffen, C. V. Caviglione, V. Fattori, A. J. Bussmann, C. Bottura, M. J. Fonseca, J. A. Vignoli, M. M. Baracat, S. R. Georgetti, W. A. Verri, R. Casagrande. Photochem. Photobiol. Sci. 16, 1162 (2017), https://doi.org/10.1039/c6pp00442c.Search in Google Scholar PubMed

[30] E. N. Okolo, D. I. Ugwu, B. E. Ezema, J. C. Ndefo, F. U. Eze, C. G. Ezema, J. A. Ezugwu, O. T. Ujam. Sci. Rep. 11, 21781 (2021), https://doi.org/10.1038/s41598-021-01292-5.Search in Google Scholar PubMed PubMed Central

[31] S. Narwal, S. Kumar, P. K. Verma. Res. Chem. Intermed. 47, 1625 (2021), https://doi.org/10.1007/s11164-020-04359-6.Search in Google Scholar

[32] C. Birnie, D. Malamud, R. Schnaare. Antimicrob. Agents Chemother. 44(9), 2514 (2000), https://doi.org/10.1128/aac.44.9.2514-2517.2000.Search in Google Scholar PubMed PubMed Central

[33] A. A. Williams, E. W. Sugandhi, R. V. Macri, J. O. Falkinham, R. D. Gandour. J. Antimicrob. Chemother. 59, 451 (2007), https://doi.org/10.1093/jac/dkl503.Search in Google Scholar PubMed

[34] L. Yang, C. Chen, T. Liang, L. Hao, Q. Gu, H. Xu, Y. Zhao, L. Jiang, X. Fan. J. Colloid Interface Sci. 649, 535 (2023), https://doi.org/10.1016/j.jcis.2023.05.168.Search in Google Scholar PubMed

[35] K. Park, Y. Park, S. Cho, W. Sun, S. Kim, D. Jung. Planta Med. 70(3), 272 (2004).Search in Google Scholar

[36] C. Sheu, E. Freese. J. Bacteriol. 115(3), 869 (1973), https://doi.org/10.1128/jb.115.3.869-875.1973.Search in Google Scholar PubMed PubMed Central

[37] Z. Ngaini, S. M. H. Fadzillaha, H. Hussain. Nat. Prod. Res. 26(10), 892 (2012), https://doi.org/10.1080/14786419.2010.502896.Search in Google Scholar PubMed

[38] Anonymous, https://www.who.int/news-room/fact-sheets/detail/tuberculosis#TB%20and%20HIV (accessed Nov 7, 2023).Search in Google Scholar

[39] L. Nguyen. Arch. Toxicol. 90, 1585 (2016), https://doi.org/10.1007/s00204-016-1727-6.Search in Google Scholar PubMed PubMed Central

[40] J. C. Palomino, A. Martin. Antibiotics 3, 317 (2014), https://doi.org/10.3390/antibiotics3030317.Search in Google Scholar PubMed PubMed Central

[41] N. Dookie, S. Rambaran, N. Padayatchi, S. Mahomed, K. Naidoo. J. Antimicrob. Chemother. 73(5), 1138–1151 (2018).10.1093/jac/dkx506Search in Google Scholar PubMed PubMed Central

[42] N. Noviany, S. Hadi, R. Nofiani, P. D. Lotulung. Phys. Sci. Rev. 8, 3897 (2023).10.1515/psr-2021-0224Search in Google Scholar

[43] C. N. Rodríguez-Silva, I. M. Prokopczyk, J. L. Dos Santos. Mini Rev. Med. Chem. 22(16), 2068 (2022), https://doi.org/10.2174/1389557522666220214093606.Search in Google Scholar PubMed

[44] P. M. Sivakumar, S. K. G. Babu, D. Mukesh. Chem. Pharm. Bull. 55(1), 44 (2007), https://doi.org/10.1248/cpb.55.44.Search in Google Scholar PubMed

[45] N. Hasan, H. Osman, S. Mohamad, W. Keng Chong, K. Awang, A. S. M. Zahariluddin. Pharmaceuticals 5, 882 (2012), https://doi.org/10.3390/ph5080882.Search in Google Scholar PubMed PubMed Central

[46] M. Climent, A. Corma, S. Iborra, A. Velty. J. Catal. 221(2), 474 (2004), https://doi.org/10.1016/j.jcat.2003.09.012.Search in Google Scholar

[47] J. McMurry. Carbonyl Alpha-Substitution Reactions, Organic Chemistry, pp. 849–857, Thomson Learning, Inc., USA, 7th ed. (2008).Search in Google Scholar
Published Online: 2024-01-24
Published in Print: 2024-03-25

© 2024 IUPAC & De Gruyter

Articles in the same Issue

  1. Frontmatter
  2. In this issue
  3. Preface
  4. The virtual conference on chemistry and its applications, VCCA-2023, 7–11 August 2023
  5. Special topic papers
  6. Recovery of wipe sampling of urban surfaces contaminated with blistering chemical warfare agents
  7. Bioremediation of cadmium contaminated soil by tea waste and impact on the accumulation of Cd in Helianthus annuus
  8. Exploring the potential of Meldrum’s acid-bearing chain extenders for mechanical recycling of PET
  9. In silico and in vitro profiling of coumarins and flavonoids for anti-Alzheimer and antioxidant activity
  10. MTT assay of human anti-breast cancer cells (MCF-7) in vitro potentials and phytochemicals screening of the root bark extracts from Cassia sieberiana
  11. Synthesis of some chalcones derivatives series and their antituberculosis activity
  12. Luminescence of silver, thulium and ytterbium doped oxyfluoride glasses
  13. Two new naturally dimers constituent from Indonesian Sesbania grandiflora plant and their bioactivity
  14. Antidiabetic and antibacterial activities of artocarpin: a flavonoid compound isolated from the root wood of the Pudau plant (Artocarpus kemando Miq.)
  15. Unraveling the influence of biomaterial’s functional groups in Cd biosorption: a density functional theory calculation
  16. Synthesis, characterization, and bioactivity test of dibutyltin(IV) dihydroxyibenzoate as disinfectant agent
  17. Computational investigation of thallium interactions with functionalized multi-walled carbon nanotubes for electrochemical sensing applications
  18. Conversion of elemental phosphorus under the electron beam irradiation
  19. Advances in understanding comproportionation and disproportionation in nickel catalysis
https://doi.org/10.1515/pac-2023-1127
Keywords for this article
antituberculosis activity; chalcones derivatives; Mycobacterium tuberculosis; VCCA–2023

Articles in the same Issue

  1. Frontmatter
  2. In this issue
  3. Preface
  4. The virtual conference on chemistry and its applications, VCCA-2023, 7–11 August 2023
  5. Special topic papers
  6. Recovery of wipe sampling of urban surfaces contaminated with blistering chemical warfare agents
  7. Bioremediation of cadmium contaminated soil by tea waste and impact on the accumulation of Cd in Helianthus annuus
  8. Exploring the potential of Meldrum’s acid-bearing chain extenders for mechanical recycling of PET
  9. In silico and in vitro profiling of coumarins and flavonoids for anti-Alzheimer and antioxidant activity
  10. MTT assay of human anti-breast cancer cells (MCF-7) in vitro potentials and phytochemicals screening of the root bark extracts from Cassia sieberiana
  11. Synthesis of some chalcones derivatives series and their antituberculosis activity
  12. Luminescence of silver, thulium and ytterbium doped oxyfluoride glasses
  13. Two new naturally dimers constituent from Indonesian Sesbania grandiflora plant and their bioactivity
  14. Antidiabetic and antibacterial activities of artocarpin: a flavonoid compound isolated from the root wood of the Pudau plant (Artocarpus kemando Miq.)
  15. Unraveling the influence of biomaterial’s functional groups in Cd biosorption: a density functional theory calculation
  16. Synthesis, characterization, and bioactivity test of dibutyltin(IV) dihydroxyibenzoate as disinfectant agent
  17. Computational investigation of thallium interactions with functionalized multi-walled carbon nanotubes for electrochemical sensing applications
  18. Conversion of elemental phosphorus under the electron beam irradiation
  19. Advances in understanding comproportionation and disproportionation in nickel catalysis
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