Issue

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

Copyright (c) 2024 Viralkumar Arvindbhai Doshi, Yogesh S. Patel

Creative Commons License

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

Novel Benzimidazole based Hydrazide-hydrazone Compounds: Synthesis, Characterization and Antimicrobial Assessment

https://doi.org/10.14233/ajchem.2024.31484
Viralkumar Arvindbhai Doshi
Department of Chemistry, Gujarat University, Ahmedabad-380009, India
https://orcid.org/0009-0008-1877-2136
Yogesh S. Patel
Department of Chemistry, Government Science College, Limkheda-389130, India
https://orcid.org/0000-0002-8588-0240

Corresponding Author(s) : Viralkumar Arvindbhai Doshi

viral_doshi2007@yahoo.com

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

Abstract

This work presents a comprehensive study on the design, synthesis, spectral characterization and antimicrobial assessment of new hydrazide-hydrazone incorporated benzimidazole compounds (6a-p). The synthesis of these compounds (6a-p) involved the condensation of benzimidazole derivative, 4-(1-methyl-5-nitro-1H-benzo[d]imidazol-2-yl)butane hydrazide with substituted aromatic aldehydes, utilizing an efficient and environmentally benign synthetic route. The IR, NMR and mass spectrometry were among the spectroscopic methods used to characterize the novel synthesized substances to confirm their chemical structures. The antimicrobial properties of the synthesized benzimidazole-based hydrazide-hydrazone compounds (6a-p) were systematically assessed against a panel of pathogenic microorganisms, including two Gram-positive and two Gram-negative bacteria and three fungi. The potency of antimicrobial drugs was assessed by determining their minimum inhibitory concentrations (MIC). The findings demonstrate that compounds 6k and 6p have moderated antibacterial action against positive-Gram bacteria S. pyogenus (MTCC 442) and S. aureus (MTCC 96), but considerable antimicrobial activity against Gram-negative bacteria E. coli (MTCC 443) and P. aeruginosa (MTCC 1688). Although every drug exhibits mild to moderate antifungal efficacy against A. niger (MTCC 282), A. clavatus (MTCC 1323) and C. albicans (MTCC 227). Furthermore, in silico prediction of compounds pharmacokinetic properties was also conducted.

Keywords

Benzimidazole Hydrazide-hydrazone Antibacterial activity Antifungal activity
Doshi, V. A., & Patel, Y. S. (2024). Novel Benzimidazole based Hydrazide-hydrazone Compounds: Synthesis, Characterization and Antimicrobial Assessment. Asian Journal of Chemistry, 36(8), 1793–1802. https://doi.org/10.14233/ajchem.2024.31484
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. M. Miethke, M. Pieroni, T. Weber, M. Brönstrup, P. Hammann, L. Halby, P.B. Arimondo, P. Glaser, B. Aigle, H.B. Bode, R. Moreira, Y. Li, A. Luzhetskyy, M.H. Medema, J.-L. Pernodet, M. Stadler, J.R. Tormo, O. Genilloud, A.W. Truman, K.J. Weissman, E. Takano, S. Sabatini, E. Stegmann, H. Brötz-Oesterhelt, W. Wohlleben, M. Seemann, M. Empting, A.K.H. Hirsch, B. Loretz, C.-M. Lehr, A. Titz, J. Herrmann, T. Jaeger, S. Alt, T. Hesterkamp, M. Winterhalter, A. Schiefer, K. Pfarr, A. Hoerauf, H. Graz, M. Graz, M. Lindvall, S. Ramurthy, A. Karlén, M. van Dongen, H. Petkovic, A. Keller, F. Peyrane, S. Donadio, L. Fraisse, L.J.V. Piddock, I.H. Gilbert, H.E. Moser and R. Müller, Nat. Rev. Chem., 5, 726 (2021); https://doi.org/10.1038/s41570-021-00313-1
  2. A.L. Buitimea, C.R. Garza-Cárdenas, J.A. Garza-Cervantes, J.A. Lerma-Escalera and J.R. Morones-Ramirea, Front. Microbiol., 11, 1669 (2020); https://doi.org/10.3389/fmicb.2020.01669
  3. Samreen, I. Ahmad, H.A. Malak and H.H. Abulreesh, J. Global Antimicrob. Resist., 27, 101 (2021); https://doi.org/10.1016/j.jgar.2021.08.001
  4. A. Gomsyan, Chem. Heterocycl. Compd., 48, 7 (2012); https://doi.org/10.100/s10593-012-0960-z
  5. S. Tahlan, S. Kumar and B. Narasimhan, BMC Chem., 13, 18 (2019); https://doi.org/10.1186/s13065-019-0521-y
  6. M. Marinescu, Antibiotics, 10, 1002 (2021); https://doi.org/10.3390/antibiotics10081002.
  7. Y. Özkay, Y. Tunali, H. Karaca and I. Isikdag, Arch. Pharm. Res., 34, 1427 (2011); https://doi.org/10.1007/s12272-011-0903-8
  8. E.M.E. Dokla, N.S. Abutaleb, S.N. Milik, K. Elbaz, M.A.W. Shalaby, D. Li, R. Al-Karaki, M. Nasr, C.D. Klein, A.M. Khaled and M.N. Seleem, Eur. J. Med. Chem., 186, 111850 (2019); https://doi.org/10.1016/j.ejmech.2019.111850
  9. D. Song and S. Ma, ChemMedChem, 11, 646 (2016); https://doi.org/10.1002/cmdc.201600041
  10. M. Gaba, S. Singh and M. Chander, Eur. J. Med. Chem., 76, 494 (2014); https://doi.org/10.1016/j.ejmech.2014.01.030
  11. R. Veerasamy, A. Roy, R. Karunakaran and H. Rajak, Pharmaceuticals, 14, 663 (2021); https://doi.org/10.3390/ph14070663
  12. M. Tonelli, G. Paglietti, V. Boido, F. Sparator, F. Marongiu, P.L. Colla, E. Marongiu and R. Loddo, Chem. Biodivers., 5, 2386 (2008); https://doi.org/10.1002/cbdv.200890203
  13. M. Tonellia, F. Novelli, B. Tasso, I. Vazzana, A. Sparatore, V. Boido, F. Sparatore, P. La Colla, G. Sanna, G. Giliberti, B. Busonera, P. Farci, C. Ibba and R. Loddo, Bioorg. Med. Chem., 22, 4893 (2014); https://doi.org/10.1016/j.bmc.2014.06.043
  14. T. Lee, Y.J. Tan and Y.E. Oon, Acta Pharm. Sin. B, 13, 478 (2023); https://doi.org/10.1016/j.apsb.2022.09.010
  15. S. Yadav, B. Narasimhan and H. Kaur, Anticancer. Agents Med. Chem., 16, 1403 (2016); https://doi.org/10.2174/1871520616666151103113412
  16. S. Tahlan, S. Kumar, S. Kakkar and B. Narasimhan, BMC Chem., 13, 66 (2019); https://doi.org/10.1186/s13065-019-0579-6
  17. G. Satija, B. Sharma, A. Madan, A. Iqubal, M. Shaquiquzzaman, M. Akhter, S. Parvez, M.A. Khan and M.M. Alam, J. Heterocycl. Chem., 59, 22 (2021); https://doi.org/10.1002/jhet.4355
  18. M. Mavvaji and S. Akkoc, ChemistrySelect, 8, e202302561 (2023); https://doi.org/10.1002/slct.202302561
  19. B. Song, E.Y. Park, K.J. Kim and S.H. Ki, Cancers, 14, 4601 (2022); https://doi.org/10.3390/cancers14194601
  20. B. Adalat, F. Rahim, W. Rehman, Z. Ali, L. Rasheed, Y. Khan, T.A. Farghaly, S. Shams, M. Taha, A. Wadood, S.A.A. Shah and M.H. Abdellatif, Pharmaceuticals, 16, 208 (2023); https://doi.org/10.3390/ph16020208
  21. H.E. Hashem and Y. El Bakri, Arab. J. Chem., 14, 103418 (2021); https://doi.org/10.1016/j.arabjc.2021.103418
  22. L. Popiolek and A. Biernasiuk, J. Enzyme Inhib. Med. Chem., 31, 62 (2016); https://doi.org/10.3109/14756366.2016.1170012
  23. L. Popiolek and A. Biernasiuk, Saudi Pharm. J., 25, 1097 (2017); https://doi.org/10.1016/j.jsps.2017.05.006
  24. L. Popiolek, A. Biernasiuk, A. Berecka, A. Gumieniczek, A. Malm and M. Wujec, Chem. Biol. Drug Des., 91, 915 (2018); https://doi.org/10.1111/cbdd.13158
  25. L. Popiolek, B. Rysz, A. Biernasiuk and M. Wujec, Chem. Biol. Drug Des., 90, 260 (2020); https://doi.org/10.1111/cbdd.13639
  26. K. Paruch, L. Popiolek and A. Biernasiuk, Appl. Sci., 11, 1180 (2021); http://doi.org/10.3390/app11031180
  27. D. Kumar, N.K. Maruthi, S. Ghosh and K. Shah, Bioorg. Med. Chem. Lett., 22, 212 (2012); https://doi.org/10.1016/j.bmcl.2011.11.031
  28. B. Yadagiri, U.D. Holagunda, R. Bantu, L. Nagarapu, V. Guguloth, S. Polepally and N. Jain, Bioorg. Med. Chem. Lett., 24, 5041 (2014); https://doi.org/10.1016/j.bmcl.2014.09.018
  29. S.S. Machakanur, B.R. Patil, D.S. Badiger, R.P. Bakale, K.B. Gudasi and S.W. Annie Bligh, J. Mol. Struct., 1011, 121 (2012); https://doi.org/10.1016/j.molstruc.2011.12.023
  30. T. Nasr, S. Bondock and M. Youns, Eur. J. Med. Chem., 76C, 539 (2014); https://doi.org/10.1016/j.ejmech.2014.02.026
  31. V. Kumar, G. Basavarajaswamy, M.V. Rai, B. Poojary and R.V. Pai, Bioorg. Med. Chem. Lett., 25, 1420 (2015); https://doi.org/10.1016/j.bmcl.2015.02.043
  32. S. Senkardes, N.K. Basu, I. Durmaz, D. Manvar, A. Basu, R. Atalay and S. Güniz-Küçükgüzel, Eur. J. Medicinal Chem., (2015); https://doi.org/10.1016/j.ejmech.2015.10.041
  33. A. Inam, S.M. Siddiqui, T.S. Macedo, D.R.M. Moreira, A.C.L. Leite, M.B.P. Soares and A. Azam, Eur. J. Med. Chem., 75, 67 (2014); https://doi.org/10.1016/j.ejmech.2014.01.023
  34. D.R. McCalla, A. Reuvers and C. Kaiser, J. Bacteriol., 104, 1126 (1970); https://doi.org/10.1128/jb.104.3.1126-1134.1970
  35. S.N. Chatterjee and S. Ghosh, Indian J. Biochem. Biophys., 16, 125 (1979).
  36. B.H. Ali, Vet. Res. Commun., 6, 1 (1983); https://doi.org/10.1007/bf02214890
  37. C.C. McOsker and P.M. Fitzpatrick, J. Antimicrob. Chemother., 33, 23 (1994); https://doi.org/10.1093/jac/33.suppl_a.23
  38. M. Jose and M. Davial, Antibiotics, 3, 39 (2014); https://doi.org/10.3390/antibiotics3010039
  39. Ö. Aslanhan, E. Kalay, F.S. Tokalo, Z. Can and E. Sahin, J. Mol. Struct., 1279, 135037 (2023); https://doi.org/10.1016/j.molstruc.2023.135037
  40. M.P. Weinstein, CLSI. Methods for Dilution Antimicrobial Suscepti-bility Tests for Bacteria That Grow Aerobically, CLSI Standard M07, edn. 11 (2018).
  41. C. Valgas, S.M. De-Souza, E.F. Smania and A. Smania Jr., Braz. J. Microbiol., 38, 369 (2007); https://doi.org/10.1590/S1517-83822007000200034
  42. I. Wiegand, K. Hilpert and R.E.W. Hancock, Nat. Protoc., 3, 163 (2008); https://doi.org/10.1038/nprot.2007.521
  43. J.P. Hughes, S. Rees, S.B. Kalindjian and K.L. Philpott, British J. Pharmacol., 162, 1239 (2010); https://doi.org/10.1111/j.1476-5381.2010.1127.x
  44. J.V. Ragavendran, D. Sriram, S.K. Patel, I.V. Reddy, N. Bharathwajan, J. Stables and P. Yogeeswari, Eur. J. Med. Chem., 42, 146 (2007); https://doi.org/10.1016/j.ejmech.2006.08.010
Read More
Author biographies is not available.
Statistic
Read Counter : 0 Download : 0