Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Antimicrobial Activity of Newly Synthesized 2,5-Disubstituted 1,3,4-Thiadiaozle Derivatives

  • Ramiz, Mahmoud M.M. (Department of Physics and Mathematical Engineering, Faculty of Electronic Engineering, Menouf, Menoufia University) ;
  • Abdel-Rahman, Adel A.H. (Department of Chemistry, Faculty of Science, Northern Border University)
  • Received : 2011.08.26
  • Accepted : 2011.10.03
  • Published : 2011.12.20
Download PDF
⟨ Previous Next ⟩

Abstract

A number of new 2,5-disubstituted 1,3,4-thiadiazole and their S- or N-substituted derivatives as well as the corresponding sugar hydrazone derivatives were synthesized and tested for their antimicrobial activity against Bacillus subtilis (Gram-positive), Pseudomonas aeruginosa (Gram-negative), and Streptomyces species (Actinomycetes). The synthesized compounds displayed different degrees of antimicrobial activities or inhibitory actions.

Keywords

References

  1. Hermakens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643-5678. https://doi.org/10.1016/S0040-4020(97)00279-2
  2. Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Foder, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385-1401. https://doi.org/10.1021/jm00036a001
  3. Krchnak, V.; Holladay, M. W. Chem. Rev. 2002, 102, 61-92. https://doi.org/10.1021/cr010123h
  4. Nfzi, A.; Ostresh, J. M.; Houghten, R. A. Chem. Rev. 1997, 97, 449-472. https://doi.org/10.1021/cr960010b
  5. Thompson, L. A.; Ellman, J. A.; Chem. Rev. 1996, 96, 555-600. https://doi.org/10.1021/cr9402081
  6. Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135-8173. https://doi.org/10.1016/0040-4020(95)00467-M
  7. Mullican, M. D.; Wilson, M. W.; Connor, D. T.; Kostlan, C. R.; Schrier, D. J.; Dyer, R. D. J. Med. Chem. 1993, 36, 1090-1098. https://doi.org/10.1021/jm00060a017
  8. Song, Y.; Connor, D. T.; Sercel, A. D.; Sorenson, R. J.; Doubleday, R.; Unangst, P. C.; Roth, B. D.; Beylin, V. G.; Gilbertsen, R. B.; Chan, K.; Schrier, D. J.; Guglietta, A.; Bornemeier, D. A.; Dyer, R. D. J. Med. Chem. 1999, 42, 1161-1169. https://doi.org/10.1021/jm980570y
  9. Boschelli, D. H.; Connor, D. T.; Bornemeier, D. A.; Dyer, R. D.; Kennedy, J. A.; Kuipers, P. J.; Okonkwo, G. C.; Schrier, D. J.; Wright, C. D. J. Med. Chem. 1993, 36, 1802-1810. https://doi.org/10.1021/jm00065a002
  10. El-Emam A. A.; Al-Deeb, O. A.; Al-Omar, M.; Lehmann, J. Bioorg. Med. Chem. 2004, 12, 5107-5113. https://doi.org/10.1016/j.bmc.2004.07.033
  11. Dogan, H. N.; Duran, A.; Rollas, S.; Sener, G.; Uysal, M. K.; Gulen, D. Bioorg. Med. Chem. 2002, 10, 2893-2898. https://doi.org/10.1016/S0968-0896(02)00143-8
  12. Hollar, B. S.; Gonsalves, R.; Shenoy, S. Eur. J. Med. Chem. 2000, 35, 267-271. https://doi.org/10.1016/S0223-5234(00)00154-9
  13. Omar, A. M. E.; Aboul-Wafa, O. M. J. Heterocycl. Chem. 1986, 23, 1339-1341. https://doi.org/10.1002/jhet.5570230514
  14. Kurtzer, F.; Katritzky, A. R.; Boulton, A. J., Eds., Advances in Heterocyclic Chemistry, Academic Press: New York, 1965; vol. 5, p 165.
  15. Foroumadi, A.; Mirzaei, M.; Shafiee, A. Farmaco 2001, 56, 621- 623. https://doi.org/10.1016/S0014-827X(01)01099-0
  16. Awad, L. F.; El Ashry, E. S. H. Carbohydr. Res. 1998, 312, 9-22. https://doi.org/10.1016/S0008-6215(98)00205-5
  17. Varvarasou, A.; Sistra-Papastaikoud, T.; Tsantili-Kakoulidou, A.; Vamvakides, A. Farmaco 1998, 53, 320-326. https://doi.org/10.1016/S0014-827X(98)00024-X
  18. Holla, B. S.; Poorjary, K. N.; Rao, B. S.; Shivananda, M. K. Eur. J. Med. Chem. 2002, 37, 511-517. https://doi.org/10.1016/S0223-5234(02)01358-2
  19. Carvalho, S. A.; Lopes, F. A. S.; Saloma, K.; Nelilma, C.; Solange, R. M. S. V.; de Castro, S. L. W.; da Silvaa, E. F.; Fragac, C. A. M. Bioorg. Med. Chem. 2008, 16, 413-421. https://doi.org/10.1016/j.bmc.2007.09.027
  20. Ashour, F. A.; Habib, N. S.; Taibbi, M.; Dine, S.; Dine, A. Farmaco 1990, 45, 134-139.
  21. Rollas, S.; Karakus, S.; Durgun, B. B.; Kiraz, M.; Erdeniz, H. Farmaco 1996, 51, 811-814.
  22. Foroumadi, A.; Soltani, F.; Moshafi, M. H.; Askari, A. O. Farmaco 2003, 58, 1023-1028. https://doi.org/10.1016/S0014-827X(03)00191-5
  23. Abdel-Rahman, A. A.-H.; El-Sayed, W. A.; Abdel-Bary, H. M.; Abdel-Megied, A. E.-S.; Morcy, E. M. Monatsh. Chem. 2008, 139, 1095-1101. https://doi.org/10.1007/s00706-008-0891-7
  24. El-Sayed, W. A.; Ramiz, M. M. M.; Abdel-Rahman, A. A.-H. Monatsh. Chem. 2008, 139, 1499-1505. https://doi.org/10.1007/s00706-008-0941-1
  25. El-Sayed, W. A.; Nassar, I. F.; Abdel-Rahman, A. A.-H. Monatsh. Chem. 2009, 140 , 365-370. https://doi.org/10.1007/s00706-008-0033-2
  26. Talath, S.; Gadad, A. K. Eur. J. Med. Chem. 2006, 41, 918-924. https://doi.org/10.1016/j.ejmech.2006.03.027
  27. Abdel-Aal, M. T.; El-Sayed, W. A.; El Ashry, E. S. H. Arch Pharm. Chem. Life Sci. 2006, 339, 356-663. https://doi.org/10.1002/ardp.200500225
  28. Abdel-Aal, M. T.; El-Sayed, W. A.; El-Kosy, S. M.; El Ashry, E. S. H. Arch Pharm. Chem. Life Sci. 2008, 341, 307-313. https://doi.org/10.1002/ardp.200700154
  29. Somogyi, L. Carbohydr. Res. 1977, 54, C14-C16. https://doi.org/10.1016/S0008-6215(77)80005-0
  30. Somogyi, L. Carbohydr. Res. 1978, 64, 289-292. https://doi.org/10.1016/S0008-6215(00)83712-X
  31. Jorgensen, J. H.; Jurnide, J. D.; Washington, J. A. American Society for Microbiology, Washington, DC, USA 1999, 1526-1543.
  32. Janssen, A. M.; Scheffer, J. J.; Svendsen, A. B. Planta Med. 1987, 53, 395-400. https://doi.org/10.1055/s-2006-962755
  33. Greenwood, Antimicrobial Chemotherapy, 4th ed, Oxford University Press: New York, 2000; p 114.

Cited by

  1. Tetrazolium Compounds: Synthesis and Applications in Medicine vol.20, pp.4, 2015, https://doi.org/10.3390/molecules20045528
  2. Synthesis of 4-Heteroaryl-Quinazoline Derivatives as Potential Anti-breast Cancer Agents vol.54, pp.1, 2017, https://doi.org/10.1002/jhet.2634