Issue

Vol. 36 No. 8 (2024): Vol 36 Issue 8, 2024

Copyright (c) 2024 Rajendra Dnyandeo Dighe Dighe

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

From Isoniazid to 2-Pyrazolines: Synthesis, In silico Behaviour and Antimicrobial Activity

https://doi.org/10.14233/ajchem.2024.31666
Geetha Birudala
Faculty of Pharmacy, Dr. M.G.R. Educational and Research Institute, Velappanchavadi, Chennai-600077, India
https://orcid.org/0000-0002-6106-4951
Gurinderdeep Singh
Department of Pharmaceutical Sciences and Drug Research, Punjabi University, Patiala-147002, India
https://orcid.org/0000-0003-0166-3685
S. Abdur Rahman Junaid Nayeem
Department of Medicinal Chemistry, NIPER-Kolkata, Chunilal Bhawan, 168, Maniktala Main Road, Kolkata-700054, India
https://orcid.org/0009-0008-7346-2763
S. Padmavathi
Department of Pharmaceutical Chemistry, Nirmala College of Pharmacy, Atmakur, Mangalagiri, Guntur-522503, India
https://orcid.org/0000-0002-4193-1798
Srinivasa Rao Pingali
Department of Pharmaceutical Chemistry, NNRG School of Pharmacy, Chowdariguda (V), Medchel, Malkajgiri District-500088, India
https://orcid.org/0000-0002-2174-9331
Vaishali
Faculty of Pharmacy, Moradabad Educational Trust Group of Institutions, Moradabad-244001, India
https://orcid.org/0000-0002-0189-5411
Rajendra Dnyandeo Dighe
Department of Pharmaceutical Chemistry, K.B.H.S.S. Trust’s Institute of Pharmacy, Malegaon, Nashik-423105, India
https://orcid.org/0009-0004-8239-0109

Corresponding Author(s) : Rajendra Dnyandeo Dighe

digherd.pharma@gmail.com

Asian Journal of Chemistry, Vol. 36 No. 8 (2024): Vol 36 Issue 8, 2024

Abstract

This study explores the synthesis, in silico behaviour and antimicrobial activity of isoniazid derived 2-pyrazolines as potential drugs for tuberculosis and bacterial infections. The investigation encompasses the synthesis, computational studies for molecular behaviour and antimicrobial efficacy assessment. Incorporating established drugs like isoniazid is explored to enhance their pharmacological properties. The synthesized compounds were characterized by analytical techniques such as IR, NMR, mass spectral analysis and elemental analysis. Synthesized pyrazolines 4a-j were evaluated for in vitro antitubercular and antibacterial activities against various biological strains. In silico analysis provides valuable insights into ADMET descriptors, confirming good pharmacokinetic properties. This suggests these compounds as templates for developing new anti-mycobacterial agents, guiding the design of novel compounds with improved therapeutic potential.

Keywords

Isoniazid 2-Pyrazolines Chalcone synthons ADMET descriptors Antitubercular activity Antibacterial activity
Birudala, G., Singh, G., Junaid Nayeem, S. A. R., Padmavathi, S., Pingali, S. R., Vaishali, & Dighe, R. D. (2024). From Isoniazid to 2-Pyrazolines: Synthesis, In silico Behaviour and Antimicrobial Activity. Asian Journal of Chemistry, 36(8), 1812–1820. https://doi.org/10.14233/ajchem.2024.31666
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. G. Mancuso, A. Midiri, S. De Gaetano, E. Ponzo and C. Biondo, Microorganisms, 11, 2277 (2023); https://doi.org/10.3390/microorganisms11092277
  2. G. Mancuso, A. Midiri, E. Gerace and C. Biondo, Pathogens, 10, 1310 (2021); https://doi.org/10.3390/pathogens10101310
  3. V.A. Dartois and E.J. Rubin, Nat. Rev. Microbiol., 20, 685 (2022); https://doi.org/10.1038/s41579-022-00731-y
  4. M.A. Ejalonibu, S.A. Ogundare, A.A. Elrashedy, M.A. Ejalonibu, M.M. Lawal, N.N. Mhlongo and H.M. Kumalo, Int. J. Mol. Sci., 22, 13259 (2021); https://doi.org/10.3390/ijms222413259
  5. M.I. Chouiter, H. Boulebd, D.M. Pereira, P. Valentão, P.B. Andrade, A. Belfaitah and A.M.S. Silva, Future Med. Chem., 12, 493 (2020); https://doi.org/10.4155/fmc-2019-0342
  6. K.T. Wong, H. Osman, T. Parumasivam, U. Supratman, M.T. Che Omar and M.N. Azmi, Molecules, 26, 2081 (2021); https://doi.org/10.3390/molecules26072081
  7. A. Burke, M. Di Filippo, S. Spiccio, A.M. Schito, D. Caviglia, C. Brullo and M. Baumann, Int. J. Mol. Sci., 24, 5319 (2023); https://doi.org/10.3390/ijms24065319
  8. H. Pourtaher, Y. Mohammadi, A. Hasaninejad and A. Iraji, RSC Med. Chem., 15, 207 (2024); https://doi.org/10.1039/D3MD00255A
  9. M. Mantzanidou, E. Pontiki and D. Hadjipavlou-Litina, Molecules, 26, 3439 (2021); https://doi.org/10.3390/molecules26113439
  10. B. Insuasty, J. Ramírez, D. Becerra, C. Echeverry, J. Quiroga, R. Abonia, S.M. Robledo, I.D. Vélez, Y. Upegui, J.A. Muñoz, V. Ospina, M. Nogueras and J. Cobo, Eur. J. Med. Chem., 93, 401 (2015); https://doi.org/10.1016/j.ejmech.2015.02.040
  11. T.M. Rangarajan and B. Mathew, Curr. Top. Med. Chem., 21, 2695 (2021); https://doi.org/10.2174/1568026621999210902123132
  12. S.N. Tandel, D.V. Kasundra and P.N. Patel, Results Chem., 6, 101119 (2023); https://doi.org/10.1016/j.rechem.2023.101119
  13. R. Kumar, H. Singh, A. Mazumder, Salahuddin and R.K. Yadav, Top. Curr. Chem., 381, 12 (2023); https://doi.org/10.1007/s41061-023-00422-z
  14. A.M. Fahim, E.H.I. Ismael and H.E.M. Tolan, Polycycl. Aromat. Compd., 1-42 (2023); https://doi.org/10.1080/10406638.2023.2266549
  15. S.R. Khan, Y. Manialawy and A.G. Siraki, Br. J. Pharmacol., 176, 4599 (2019); https://doi.org/10.1111/bph.14867
  16. D.C. Santos, R.R. Henriques, M.A.A.L. Junior, A.B. Farias, T.L.C. Nogueira, J.V.F. Quimas, N.C. Romeiro, L.L. Silva and A.L.F. Souza, Bioorg. Med. Chem., 28, 115470 (2020); https://doi.org/10.1016/j.bmc.2020.115470
  17. M.A. Al-Omar, A.E.E. Amr and R.A. Al-Salahi, Arch. Pharm., 343, 648 (2010); https://doi.org/10.1002/ardp.201000088
  18. F. Martins, S. Santos, C. Ventura, R. Elvas-Leitão, L. Santos, S. Vitorino, M. Reis, V. Miranda, H.F. Correia, J. Aires-de-Sousa, V. Kovalishyn, D.A.R.S. Latino, J. Ramos and M. Viveiros, Eur. J. Med. Chem., 81, 119 (2014); https://doi.org/10.1016/j.ejmech.2014.04.077
  19. P.S. Patil, S.L. Kasare, N.B. Haval, V.M. Khedkar, P.P. Dixit, E.M. Rekha, D. Sriram and K.P. Haval, Bioorg. Med. Chem. Lett., 30, 127434 (2020); https://doi.org/10.1016/j.bmcl.2020.127434
  20. H. Bayrak, A. Demirbas, N. Demirbas and S.A. Karaoglu, Eur. J. Med. Chem., 44, 4362 (2009); https://doi.org/10.1016/j.ejmech.2009.05.022
  21. N. Nayak, J. Ramprasad and U. Dalimba, Bioorg. Med. Chem. Lett., 25, 5540 (2015); https://doi.org/10.1016/j.bmcl.2015.10.057
  22. K. Mezgebe, Y. Melaku and E. Mulugeta, ACS Omega, 8, 19194 (2023); https://doi.org/10.1021/acsomega.3c01035
  23. D.A. Filimonov, A.A. Lagunin, T.A. Gloriozova, D.S. Druzhilovskii, A.V. Rudik, P.V. Pogodin and V.V. Poroikov, Chem. Heterocycl. Compd., 50, 444 (2014); https://doi.org/10.1007/s10593-014-1496-1
  24. A. Daina, O. Michielin and V. Zoete, Sci. Rep., 7, 42717 (2017); https://doi.org/10.1038/srep42717
  25. D.S. Karlov, S. Sosnin, I.V. Tetko and M.V. Fedorov, RSC Adv., 9, 5151 (2019); https://doi.org/10.1039/C8RA10182E
  26. S.G. Franzblau, R.S. Witzig, J.C. McLaughlin, P. Torres, G. Madico, A. Hernandez, M.T. Degnan, M.B. Cook, V.K. Quenzer, R.M. Ferguson and R.H. Gilman, J. Clin. Microbiol., 36, 362 (1998); https://doi.org/10.1128/JCM.36.2.362-366.1998
  27. CLSI, M100 Performance Standards for Antimicrobial Susceptibility Testing, CLSI; Wayne, PA, USA, edn. 29 (2019).
  28. C.-B. Kerine and J.-F. Delhomel 1,3-Diphenylprop-2-en-1-one Derivative Compounds, Preparation Method thereof and Uses of Same, US Patent, US007547729B2 (2009).
Read More
Author biographies is not available.
Statistic
Read Counter : 0 Download : 0