Synthesis and antimicrobial and antitumor activitiy of some new (1,2,4) triazole-5-one derivatives
Synthesis and antimicrobial and antitumor activitiy of some new (1,2,4) triazole-5-one derivatives
4-[Arylidene-amino]-3-thiophen-2-ylmethyl-4,5-dihydro[1,2,4]triazole-5-one compounds (3a-g) with Schiff base character were obtained from the reaction of 4-amino-3-thiophen-2-ylmethyl-4,5-dihydro-1H-[1,2,4]triazole- 5-one (2) with various aldehydes. 1-(2-Oxo-2-phenyl-ethyl)-4-[arylidene-amino]-3-thiophen-2-ylmethyl-4,5- dihydro-1H-[1,2,4]triazole-5-ones (4a-g) were synthesized from the reaction of corresponding compounds 3ag with bromoacetophenone. 1-(2-Hydroxy-2-phenyl-ethyl)-3-thiophen-2-ylmethyl-4-[aryl-amino]4,5-dihydro- 1H-[1,2,4]triazole-5-ones (5a-g) and 1-(2-hydroxy-2-phenyl-ethyl)-3-thiophen-2-ylmethyl-4-[arylidene-amino]4,5- dihydro-1H-[1,2,4]triazole-5-ones (6b,d,e) were obtained from the selective reduction of 1-(2-oxo-2-phenylethyl)- 4-[arylidene-amino]-3-thiophen-2ylmethyl-4,5-dihydro-1H-[1,2,4] triazole-5-ones (4) with NaBH4. They were characterized by IR, $^1 H-NMR$, $^{13}C-NMR$, and elemental analyses. Compounds 2, 3a, 3c, 3g, 4f, 5b, and 5g showed good antifungal activity against yeast-like fungi. Compounds selected by the National Cancer Institute (NCI, USA) were investigated for antitumor activity.
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- 1. The Merck & Co. Inc. Index, Whitehouse Station , NJ, USA, 2001, 3737.
- 2. Zajac, M.; Pawelezyk, E.; Chemia Lekow, AM Poznan 2000, 188.
- 3. The Merck & Co. Inc. Index, Whitehouse Station , NJ, USA, 2001, 320.
- 4. The Merck &Co. Inc. Index,Whitehouse Station, NJ, USA, 2001, 8324.
- 5. Foroumadi, A., Soltani, F., Moshafi, M. F., Ashraf-Askari, R. IL Farmaco 2003, 58, 1023-1028.
- 6. Foroumadi, A., Mansouri, S., Kiani, Z., Rahmani, A. Eur. J. Med. Chem. 2003, 38, 851-854.
- 7. Foroumadi, A., Mirzai, M., Shafiee, A. IL Farmaco 2001, 56, 621-623.
- 8. Ulusoy, N., Gürsoy, A., Ötük, G. IL Farmaco 2001, 56, 947-952.
- 9. İskeleli, N., Işık, S¸., Sancak, K., Şaşmaz, S., Ünver, Y., Er, M. Acta Crytallographica Section C 2005, 61, 363-364.
- 10. Collin, X., Sauleau, A., Coulon, J. Bioorg. Med.Chem. 2003, 13, 2601-2605.
- 11. Demirayak, S¸., Benkli, K., Güven, K. Eur. J. Chem. 2000, 35, 1037-1040.
- 12. Demirbaş, A., Johansson, C. B., Duman, N., İkizler, A. A. Acta Pol. Pharm.-Drug Res. 1996, 53, 117-121.
- 13. İkizler, A. A., Uçar, F., Demirbaş, N., Yasa, I., Demirbaş, A. Ind. J. Pharm. Sci. 1999, 61, 271-274.
- 14. Yüksek, H., Demirbaş, A., İkizler, A., Johansson, C. B., Çelik, C., İkizler, A. A. Arzn.-Forsh. Drug Res. 1997, 47, 405-409.
- 15. Turan-Zitouni, G., Sıvacı, M. F., Kılıç, S., Erol, K. Eur. J. Chem. 2001, 36, 685-689.
- 16. İkizler, A. A., Uzunali, E., Demirbaş, A. Indian J. Pharm. 2000, 5, 289-292.
- 17. Holla, B. S., Poorjary, K. N., Tao, B. S., Shivananda, M. K. Eur. J. Med. Chem. 2002, 37, 511-517.
- 18. Holla, B. S., Sarojini, B. K., Rao, B. S., Akberali, P. M., Kumari, N. S., Shatty, V. Il Farmaco 2001, 56, 565-570.
- 19. Goss, P. E.; Strasser-Weippl, K. Best Pract. Res. Clin. End. Met. 2004, 18, 113-130.
- 20. Santen, J. R. Steroids 2003, 68, 559-567.
- 21. Clemons, M.; Colemon, R. E.; Verma, S. Cancer Treat. Rew. 2004, 30, 325-332.
- 22. Chen, S., Kao, Y. C., Laughton, C. A. J. Steroid Biochem. 1997, 61, 107-115.
- 23. İkizler A. A., Sancak, K. Collect. Czech. Commun. 1995, 60, 903-909.
- 24. Demirbaş N., Uğurluoğlu R., Turk. J. Chem. 2004, 28, 679-690.
- 25. Yılmaz, I., Arslan, N. B., Kazak, C., Sancak, K., Ünver, Y. Acta Crytallographica Section E 2006, 62, 3067-3068.
- 26. Ustabaş, R., Çoruh, U., Sancak, K., Ünver Y., Vazquez-Lopez, Ezequiel M. Acta Crystallographica Section E 2007, 63, 2982-2983.
- 27. Perez, C., Bazerque, M. Acta Biol. Med. Exp. 1990, 15, 113-115.
- 28. Ahmad, I., Mehmood, Z., Mohammed, F. J. Ethnopharmacol. 1998, 62, 183-193.
- 29. Gray, G. D. and Wickstrom, E. Biotechniques, 1996, 21, 780-782.