Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis, Characterization and Antimicrobial Activity of New Thiadiazole Derivatives

  • Mullick, Pooja (Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Jamia Hamdard (Hamdard University)) ;
  • Khan, Suroor A. (Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Jamia Hamdard (Hamdard University)) ;
  • Verma, Surajpal (Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Jamia Hamdard (Hamdard University)) ;
  • Alam, Ozair (Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Jamia Hamdard (Hamdard University))
  • Received : 2009.12.02
  • Accepted : 2010.02.16
  • Published : 2010.08.20
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Abstract

A series of thiadiazole derivatives were synthesized with differently substituted benzoic acids which were cyclized to give differently substituted thiazolidin-4-one. Elemental analysis, IR, $^1H$ NMR, $^{13}C$ NMR and mass spectral data confirmed the structure of the newly synthesized compounds. The derivatives of these moieties were evaluated for antimicrobial activity. Most of the synthesized compounds showed good antimicrobial activity at 200 and $100\;{\mu}g/mL$. Compounds showed most significant antibacterial activity against gram negative test organism Escherichia coli and most significant antifungal activity against test organisms Aspergillus niger and Candida albicans. It was observed that compounds with $OCH_3$ at 3, 4 position of phenyl ring [5(a-l)] were more potent against microbes as compared to compounds having unsubstituted phenyl ring [4(a-l)].

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References

  1. Bloom, B. R.; Cohen, M. L.; Donnenberg, M. S.; Walsh, C.; Aderem, A.; Ulevitch, R. J.; Park, S. H.; Bendelac, A.; Seder, R. A.; Hill, A. V. S.; Fraser, C. M.; Eisen, J. A.; Salzberg, S. L. Nature 2000, 406, 759. https://doi.org/10.1038/35021201
  2. Cohen, M. L. Nature 2000, 406, 762. https://doi.org/10.1038/35021206
  3. Almasirad, A.; Tabatabai, S. A.; Faizi, M.; Kebriaeezadeh, A.;Mehrabi, N.; Dalvandi, A.; Shafiee, A. Bioorg. Med. Chem. Lett.2002, 10, 2893. https://doi.org/10.1016/S0968-0896(02)00143-8
  4. Foroumadi, A.; Kargar, Z.; Sakhteman, A.; Sharifzadeh, Z.; Feyzmohammadi,R.; Kazemi, M.; Shafiee, A. Bioorg. Med. Chem. Lett. 2006, 16, 1164. https://doi.org/10.1016/j.bmcl.2005.11.087
  5. Michael, R.; Stillings, M. R.; Welbourn, A. P.; Walter, D. S. J. Med. Chem. 1986, 29, 2280. https://doi.org/10.1021/jm00161a025
  6. Schenone, S. S.; Brullo, C. C.; Bruno, O. O.; Bondavalli, F. F.; Ranise, A. A.; Filippelli, W. W.; Rinaldi, B. B.; Capuano, A. A.; Falcone, G. G. Bioorg. Med. Chem. 2006, 14, 1698. https://doi.org/10.1016/j.bmc.2005.10.064
  7. Clerici, F.; Pocar, D.; Guido, M.; Loche, A.; Perlini, V.; Brufani, M. J. Med. Chem. 2001, 44, 931. https://doi.org/10.1021/jm001027w
  8. Kaya, A. B.; Chizhov, N. P.; Chigareva, N. G. Pharm. Chem. Jour. 1978, 12, 66.
  9. Tuncbilek, M.; Altanlar, N. Il Farmaco 1999, 54, 475. https://doi.org/10.1016/S0014-827X(99)00054-3
  10. Ergene, N.; Capan, G. Il Farmaco 1994, 49, 449.
  11. Diurno, M.V.; Mazzoni, O.; Izzo, A. A.; Bolognese, A. Il Farmaco 1997, 52, 237.
  12. Verma, A.; Saraf, S. K.; Eur. J. Med. Chem. 2008, 43, 897. https://doi.org/10.1016/j.ejmech.2007.07.017
  13. Chavan, A. A.; Pai, N. R. Arkivoc 2007, 148.
  14. Diurno, M. V.; Mazzoni, O.; Correale, G.; Monterry, I. G.; Il Farmaco 1999, 54, 579. https://doi.org/10.1016/S0014-827X(99)00064-6
  15. Shafiee, A.; Naimi, E.; Mansobi, P.; Foroumadi, A.; Shekari, M. J. Het. Chem. 1995, 32, 1235. https://doi.org/10.1002/jhet.5570320424
  16. Altmtas, H.; Ates, O.; Kocabalkanli, A.; Birteksoz, S.; Otuk, G. Ind. J. Chem. 2005, 44B, 585.
  17. Indian Pharmacopoeia 1996, Appendix 9, A-100.
  18. Karegoudar, P.; Karthikeyan, M. S.; Prasad, D. J.; Mahalinga, M.; hivaramholla,B.; Kumari, N. S. Eur. J. Med. Chem. 2008, 43, 261. https://doi.org/10.1016/j.ejmech.2007.03.014
  19. Skaggs, B. A. A.; Motley, M.; Warnock, D. W.; Morrissor, C. J. J. Clin. Microbial. 2000, 38, 2254.

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