Synthesis of some new biheterocyclic triazole derivatives and evaluation of their antimicrobial activity
Yıl: 2010 Cilt: 34 Sayı: 2 Sayfa Aralığı: 165 - 180 Metin Dili: İngilizce İndeks Tarihi: 29-07-2022
Synthesis of some new biheterocyclic triazole derivatives and evaluation of their antimicrobial activity
Öz: 2-{3-(4-Substitutedbenzyl)-4-[2-(1H-indol-3-yl)ethyl]-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl}-N' -(arylmethylene) acetohydrazides (5a-g), 4-amino-2-{3-(4-substitutedbenzyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1- yl}-N' -(arylmethylene)acetohydrazides (6a,b), and 4-[2-(1H-indol-3-yl)ethyl]-5-(4-substitutedbenzyl)-2-{[5- (phenylamino)-1,3,4-thiadiazol-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-ones (8a,b) were synthesized starting from 4-alkyl-5-(4-substitutedbenzyl)-2,4-dihydro-3H-1,2,4-triazol-3-ones (2a-c) by several steps and their structures were well characterized by elemental analyses, IR, 1H-NMR, 13C-NMR, and mass spectral studies. They were also screened for their microbial activities. The obtained antimicrobial activity results revealed that 12 among the 24 compounds tested displayed variable growth inhibition effects on the tested grampositive and gram-negative bacterial strains. None of the compounds showed antifungal activity against yeast-like fungi.
Anahtar Kelime: Konular:
Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık
- 1. Ram, V. J. J. Het. Chem. 1998, 2, 253-256.
- 2. Yu, D.; Huiyuan, G. Bioorg. Med. Chem. Lett. 2002, 12, 857-859.
- 3. Bonde, C.; Gaikwad, N. J. Bioorg. Med. Chem. 2004, 12, 2151-2161.
- 4. Koca, M.; Servi, S.; Kirilmis, C.; Ahmedzade, M.; Kazaz, C.; ¨Ozbek, B.; ¨Ot¨uk, G. Eur. J. Med. Chem. 2005, 40, 1351-1358.
- 5. Sbardella, G.; Mai, A.; Artico, M.; Loddo, R.; Setzuc, M. G.; La Collac, P. Bioorg. Med. Chem. Lett. 2004, 14, 1537-1541.
- 6. Karalı, N.; G¨ursoy, A.; Kandemirli, F.; Shvets, N., Kaynak, F. B.; ¨Ozbey, S.; Kovalishyn V.; Dimogloc, A. Bioorg. Med. Chem. 2007, 15, 5888-5904.
- 7. Leboho, T. C.; Michael, J. P.; van Otterlo, W. A. L.; van Vuuren, S. F.; de Koning, C. B. Bioorg. Med. Chem. Lett. 2009, 19, 4948-4951.
- 8. Kutschy, P.; Mojmir, S.; Andreani, A.; Dzurilla, M.; Kov´acik, V.; Alf¨odi J.; Rossi, M.; Gramatov´a, M. Tetrahedron 2002, 58, 9029-9039.
- 9. Ryu, C. K.; Lee, J. Y.; Park, R. E.; Ma, M. Y.; Nho, J. H. Bioorg. Med. Chem. Lett. 2007, 17, 127-131.
- 10. Samosorn, S.; Bremner, J. B.; Ball, A.; Lewis, K. Bioorg. Med. Chem. 2006, 14, 857-865.
- 11. Kaplancıklı, Z. A.; Turan-Zitouni, G.; ¨ Ozdemir, A.; Revial, G. Eur. J. Med. Chem. 2008, 43, 155-159.
- 12. K¨u¸c¨ukg¨uzel, S. G.; Rollas, S.; Erdeniz, H.; Kiraz, M. Eur. J. Med. Chem. 1999, 34, 153-160.
- 13. Y¨uksek, H.; Demirba¸s, A.; Ikizler, A.; Johansson, C. B.; C¸elik, C. Ikizler, A. A. Arzn.-Forsh. Drug Res. 1997, 47, 405-409.
- 14. Tozkoparan, B.; G¨okhan, N.; Aktay, G.; Ye¸silada, E.; Ertan, M. Eur. J. Med. Chem. 2000, 35, 743-750.
- 15. Ikizler, A. A.; Uzunali, E.; Demirba¸s, A. Indian J. Pharm. Sci. 2000, 5, 289-292.
- 16. Demirbas, N.; Ugurluoglu, R.; Demirbas, A. Bioorg. Med. Chem. 2002, 10, 3717-3723.
- 17. Turan-Zitouni, G.; Sıvacı, M.; Kılı¸c, F. S.; Erol, K. Eur. J. Med. Chem. 2001, 36, 685-689.
- 18. Demirbas, A.; Johansson, C. B.; Duman, N.; Ikizler, A. Acta Pol. Pharm.-Drug Res. 1996, 53, 117-123.
- 19. Ikizler, A.; Demirbas, N.; Ikizler, A. A. J. Het. Chem. 1996, 33, 1765-1769.
- 20. Malbec, F.; Milcent, R.; Vicart ,P.; Bure, A. M. J. Het. Chem. 1984, 21, 1769-1774.
- 21. Zhang, J.; Chang, C-W. T. J. Org. Chem. 2009, in press.
- 22. Goss, P. E. Best Practice Res. 2004, 18, 113-130.
- 23. Yu, L. T.; Ho, M. T.; Chang, C. Y. and Yang, T. K. Tetrahedron: Asim., 2007, 18, 949-962.
- 24. Gupta, A.; Unadkat, J. D. and Mao, Q. J. Pharm. Sci. 2007, 96, 3226-3235.
- 25. Schiller, S. D. and Fung, H. B.; Clinical Therapeutics 2008, 29, 1862-1886.
- 26. Ashok, M.; Holla, B. S. and Poojary, B., Eur. J. Med. Chem. 2007, 42, 1095-1101.
- 27. Rao, B. M.; Sangaraju, S.; Srinivasu, M. K.; Madhavan, P.; Devi, M. L.; Kumar, P. R.; Candrasekhar, P.; Arpitha, Ch.; Balaji, T. S. J. Pharm. Biomed. Anal. 2006, 41, 1146-1151.
- 28. Hancu, G.; Gaspar, A.; Gyeresi, A. J. Biochem. Biophys. Methods 2007, 69, 251-259.
- 29. Bajetti, E.; Zilembo, N.; Bichisao, E.; Pozzi, P.; Toffolatti, T. Critical Reviews in Oncology: Hematology 2000, 33, 137-142.
- 30. Holla, B. S.; Shivananda, M. K.; Shenoy, M. S.; Antony, G. Il Farmaco 1998, 53, 531-535.
- 31. Holla, B. S.; Mahalinga, M.; Karthikeyan, M. S.; Poojary, B.; Akberali, P. M.; Kumari, N. S. Eur. J. Med. Chem. 2005, 40, 1173-1178.
- 32. Holla, B. S.; Rao, B. S.; Shridhara, K.; Akberali, P. M. Il Farmaco 2000, 55, 338-344.
- 33. Holla, B. S.; Veerendra, M. K. Shivananda, B. Poojary, B. Eur. J. Med. Chem. 2003, 38, 759-767.
- 34. Ashok, M.; Holla, B. S.; Poojary, B. Eur. J. Med. Chem. 2007, 42, 1095-1101.
- 35. National Committee for Clinical Laboratory Standards 1993. NCCLS Document M7-A3, 13, (25), Willanova, PA., USA.
- 36. Milcent, R.; Redeuilh, C. J. Het. Chem. 1979, 16, 403-407.
- 37. Demirbas, N.; Demirbas, A., Karaoglu, S. A.; C¸ elik, E. Arkivoc 2005, (i ), 75-91.
- 38. Bayrak, H.; Demirbas, A.; Demirbas, N.; Alpay-Karaoglu, S. Eur. J. Med. Chem. 2009, 44, 1057-1066.
- 39. Demirbas, A.; Sahin, D.; Demirbas, N.; Alpay-Karaoglu, S. Eur. J. Med. Chem. 2009, 44, 2896-2903.
- 40. Demirbas, N.; Karaoglu, S. A.; Demirbas, A.; Sancak, K. Eur. J. Med. Chem. 2004, 39, 793-804.
- 41. Demirba¸s, A. Turk. J. Chem. 2004, 28, 311-323.
- 42. Galic, N.; Peric, B.; Kojic-Prodic, B.; Cimerman, Z. J. Mol. Stuc. 2001, 559, 187-194.
- 43. Wyrzykiewicz, E.; Prukah, D. J. Het. Chem. 1998, 35, 381-387.
APA | BEKTAŞ H, DEMİRBAŞ A, DEMİRBAŞ N, Alpay Karaoğlu Ş (2010). Synthesis of some new biheterocyclic triazole derivatives and evaluation of their antimicrobial activity. , 165 - 180. |
Chicago | BEKTAŞ Hakan,DEMİRBAŞ Ahmet,DEMİRBAŞ NESLİHAN,Alpay Karaoğlu Şengül Synthesis of some new biheterocyclic triazole derivatives and evaluation of their antimicrobial activity. (2010): 165 - 180. |
MLA | BEKTAŞ Hakan,DEMİRBAŞ Ahmet,DEMİRBAŞ NESLİHAN,Alpay Karaoğlu Şengül Synthesis of some new biheterocyclic triazole derivatives and evaluation of their antimicrobial activity. , 2010, ss.165 - 180. |
AMA | BEKTAŞ H,DEMİRBAŞ A,DEMİRBAŞ N,Alpay Karaoğlu Ş Synthesis of some new biheterocyclic triazole derivatives and evaluation of their antimicrobial activity. . 2010; 165 - 180. |
Vancouver | BEKTAŞ H,DEMİRBAŞ A,DEMİRBAŞ N,Alpay Karaoğlu Ş Synthesis of some new biheterocyclic triazole derivatives and evaluation of their antimicrobial activity. . 2010; 165 - 180. |
IEEE | BEKTAŞ H,DEMİRBAŞ A,DEMİRBAŞ N,Alpay Karaoğlu Ş "Synthesis of some new biheterocyclic triazole derivatives and evaluation of their antimicrobial activity." , ss.165 - 180, 2010. |
ISNAD | BEKTAŞ, Hakan vd. "Synthesis of some new biheterocyclic triazole derivatives and evaluation of their antimicrobial activity". (2010), 165-180. |
APA | BEKTAŞ H, DEMİRBAŞ A, DEMİRBAŞ N, Alpay Karaoğlu Ş (2010). Synthesis of some new biheterocyclic triazole derivatives and evaluation of their antimicrobial activity. Turkish Journal of Chemistry, 34(2), 165 - 180. |
Chicago | BEKTAŞ Hakan,DEMİRBAŞ Ahmet,DEMİRBAŞ NESLİHAN,Alpay Karaoğlu Şengül Synthesis of some new biheterocyclic triazole derivatives and evaluation of their antimicrobial activity. Turkish Journal of Chemistry 34, no.2 (2010): 165 - 180. |
MLA | BEKTAŞ Hakan,DEMİRBAŞ Ahmet,DEMİRBAŞ NESLİHAN,Alpay Karaoğlu Şengül Synthesis of some new biheterocyclic triazole derivatives and evaluation of their antimicrobial activity. Turkish Journal of Chemistry, vol.34, no.2, 2010, ss.165 - 180. |
AMA | BEKTAŞ H,DEMİRBAŞ A,DEMİRBAŞ N,Alpay Karaoğlu Ş Synthesis of some new biheterocyclic triazole derivatives and evaluation of their antimicrobial activity. Turkish Journal of Chemistry. 2010; 34(2): 165 - 180. |
Vancouver | BEKTAŞ H,DEMİRBAŞ A,DEMİRBAŞ N,Alpay Karaoğlu Ş Synthesis of some new biheterocyclic triazole derivatives and evaluation of their antimicrobial activity. Turkish Journal of Chemistry. 2010; 34(2): 165 - 180. |
IEEE | BEKTAŞ H,DEMİRBAŞ A,DEMİRBAŞ N,Alpay Karaoğlu Ş "Synthesis of some new biheterocyclic triazole derivatives and evaluation of their antimicrobial activity." Turkish Journal of Chemistry, 34, ss.165 - 180, 2010. |
ISNAD | BEKTAŞ, Hakan vd. "Synthesis of some new biheterocyclic triazole derivatives and evaluation of their antimicrobial activity". Turkish Journal of Chemistry 34/2 (2010), 165-180. |