Synthesis and antimicrobial activities of some new 1,2,4-triazole derivatives

DEMİRBAŞ, NESLİHAN; DEMİRBAŞ, Ahmet; BEKTAŞ, Hakan; Alpay Karaoğlu, Şengül; BAYRAK, Hacer

Synthesis and antimicrobial activities of some new 1,2,4-triazole derivatives

Hacer BAYRAK, (Karadeniz Teknik Üniversitesi, Fen Edebiyat Fakültesi, Kimya Bölümü, Trabzon, Türkiye)

Ahmet DEMİRBAŞ, (Karadeniz Teknik Üniversitesi, Fen Edebiyat Fakültesi, Kimya Bölümü, Trabzon, Türkiye)

Hakan BEKTAŞ, (Giresun Üniversitesi, Kimya Bölümü, Giresun, Türkiye)

Şengül Alpay KARAOĞLU, (Giresun Üniversitesi, Fen Fakültesi, Biyoloji Bölümü, Giresun, Türkiye)

NESLİHAN DEMİRBAŞ (Karadeniz Teknik Üniversitesi, Fen Edebiyat Fakültesi, Kimya Bölümü, Trabzon, Türkiye)

Turkish Journal of Chemistry

3 0

Yıl: 2010 Cilt: 34 Sayı: 6 Sayfa Aralığı: 835 - 846 Metin Dili: İngilizce İndeks Tarihi: 29-07-2022

Synthesis and antimicrobial activities of some new 1,2,4-triazole derivatives

Öz:

The synthesis of ethyl [3-(cyanomethyl)-5-alkyl-4H -1,2,4-triazol-4-yl]carbamates (2a-d) was performed starting from ethyl 2-[ethoxy(4-(aryl)methylene]hydrazinecarboxylates (1a, 1b). The treatment of 2a with thiosemicarbazide afforded ethyl [3-[(5-amino-1,3,4-thiadiazol-2-yl)methyl]-5-(4-nitrophenyl)-4H-1,2,4- triazol-4-yl]carbamates (3a), whereas compound 2b produced 5-{[4-amino-5-(4-methylphenyl)-4H -1,2,4- triazol-3-yl]methyl}-1,3,4-thiadiazol-2-amine (3b) in the same reaction conditions. The treatment of tert - butyl 2-[2-(4-chlorophenyl)-1-ethoxyethylidene]hydrazinecarboxylate (5) with malonohydrazide or cyanoacethydrazide gave the corresponding 1,2,4-triazol-ylcarbamate derivatives (6 or 9); then the hydrolysis of these compounds resulted in the formation of 3-{[4-amino-5-(4-chlorobenzyl)-4H -1,2,4-triazol-3-yl]methyl}- 5-(4-chlorobenzyl)-4H -1,2,4-triazol-4-amine (7) and [4-amino-5-(4-chlorobenzyl)-4H -1,2,4-triazole-3-yl]acetonitrile (10), respectively. The synthesis of the Schiff base derivatives 3-(4-chlorobenzyl)-5-{[5-(4-chlorobenzyl)- 4-[(2-hydroxyphenyl-methylene)amino]-4H -1,2,4-triazol-3-yl]methyl}-N-(2-hydroxyphenylmethylene)- 4H-1,2,4-triazol-4-amine (8), and (5-(4-chlorobenzyl)-4-{[(2,6-dichlorophenyl)methylene]amino}-4H -1,2,4- triazol-3-yl)acetonitrile (12) was performed from the reaction of compounds 7 and 10 with salicyl aldehyde (for 8) or 2,6-dichlorobenzaldehyde (for 12), respectively. The treatment of compounds 5 or 10 with thiosemicarbazide gave 5-{[4-amino-5-(4-chlorobenzyl)-4H -1,2,4-triazol-3-yl]methyl}-1,3,4-thiadiazol- 2-amine (11). All the newly synthesized compounds were screened for their antimicrobial activities and were found to possess good or moderate antimicrobial activity.

Anahtar Kelime:

Konular: Mühendislik, Kimya

Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık

1. Roy, B.; Chakraborty, A.; Ghosh S. K.; Basak A. Bioorg. Med. Chem. Lett., 2009, 19, 7007-7010.
2. Dye, C.; Williams, B. G. Sci. Transl. Med., 2009, 1, 3-8.
3. Dye, C. Lancet, 2006, 367, 938-940.
4. Koca, M.; Servi, S.; Kirilmis, C.; Ahmedzade, M.; Kazaz, C.; Özbek, B.; Ötük, G. Eur. J. Med. Chem., 2005, 40, 1351-58.
5. Zalavadiya, P.; Tala, S.; Akbari, J.; Joshi, H. Arch. Pharm. Chem. Life Sci., 2009, 342, 469-475.
6. Bekhit, A. A.; El-Sayed, O. A.; Aboulmagd, E.; Park, J. Y. Eur. J. Med. Chem., 2004, 39, 249-255.
7. Farghaly, J. Y.; Bekhit, A. A.; Park, J. Y. Arch. Pharm. Pharm. Med. Chem., 2000, 333, 53-57.
8. Dixit, P. P.; Patil, V. J.; Nair, P. S.; Jain, S.; Sinha, N.; Arora, S. K. Eur. J. Med. Chem., 2006, 41, 423-428.
9. Hassan, E.; Al-Ashmawi, M. I.; Abdel-Fattah, B. Pharmazie 1983, 38, 833-835.
10. Goswami, B. N.; Kataky, J. C. S.; Baruah, J. N. J. Heterocycl. Chem., 1986, 23, 1439-1442.
11. Eweiss, N. F.; Bahajaj, A. A.; Elsherbini, E. A. J. Heterocycl. Chem., 1986, 23, 1451-1458.
12. Tsotinis, A.; Varvaresou, A.; Calageropoulou, T.; Papastaikoudi, T. S.; Tiligada, A. Arzneim. Forsch./Drug Res., 1997, 47, 307-310.
13. Garoufalias, S. S. P.; Todoulou, O. G.; Filippatos, E. C.; Valiraki, A. E. P.; Chytirogiou-Lada, A. Arzneim. Forsch./Drug Res., 1998, 48, 1019-1023.
14. Sui, Z.; Guan, J.; Hlasta, D. J.; Macielag, M. J.; Foleno, B. D.; Goldschmidt, R. M.; Loeloff, M. J.; Webb, G. C.; Barrett, J. F. Bioorg. Med. Chem. Lett., 1998, 8, 1929-1934.
15. Demirba¸s, N.; U˘gurluo˘glu, R. Turk. J. Chem., 2004, 28, 679-690.
16. Holla, B. S.; Gonsalves, R.; Shenoy, S. Il Farmaco, 1998, 53, 574-578.
17. Holla, B. S.; Poorjary, N. K.; Rao, S. B.; Shivananda, M. K. Eur. J. Med. Chem., 2002, 37, 511-517.
18. Y¨uksek, H.; Demirbas, A.; Ikizler, A.; Johansson, C. B.; C¸ elik, C.; Ikizler, A.A. Arzneim. Forsh. Drug Res., 1997, 47, 405-409.
19. Ghorab, M. M.; El-Sharief, A. M. S.; Ammar, Y. A.; Mohamed, S. I. Il Farmaco, 2000, 55, 354-361.
20. Kücükgüzel, S. G.; Rollas, S.; Erdeniz, H.; Kiraz, M. Eur. J. Med. Chem., 1999, 34, 153-159.
21. Tozkoparan, B.; Gökhan, N.; Aktay, G.; Yeşilada, E.; Ertan, M. Eur. J. Med. Chem., 2000, 35, 743-750.
22. Ikizler, A. A.; Uzunali, E.; Demirba¸s, A. Indian J. Pharm. Sci., 2000, 5, 289-292.
23. Demirbas, N., Alpay-Karaoglu, S.; Demirbas, A.; Sancak, K. Eur. J. Med. Chem., 2004, 39, 793-804.
24. Bayrak, H.; Demirbaş, A.; Alpay-Karaoglu, S.; Demirbaş, N. Eur. J. Med. Chem., 2009, 44, 1057-1066.
25. Bayrak, H.; Demirbas, A.; Demirbas, N.; Alpay-Karaoglu, S. Eur. J. Med. Chem., 2009, 44, 4362-4366.
26. Demirbas, A.; Sahin, D.; Demirbas, N.; Alpay-Karaoglu, S. Eur. J. Med. Chem., 2009, 44, 2896-2903.
27. Demirbas, N.; Ugurluoglu, R.; Demirbas, A. Bioorg. Med. Chem., 2002, 10, 3717-3723.
28. Demirbaş, N.; Uğurluoğlu, R.; Turk. J. Chem., 2004, 28, 559-571.
29. Demirbas, N.; Demirbas, A.; Alpay-Karaoglu, S. Russian J. Bioorg. Chem., 2005, 31, 430-440.
30. Pesson, M.; Dupin, S.; Antoine, M. Bull. Soc. Chim., France, 1962, 1364-1371.
31. Demirbaş, A.; Demirbaş, N.; İkizler, A. A. Indian J. Heterocycl. Chem., 1999, 9, 87-94.
32. National Committee for Clinical Laboratory Standards, NCCLS Document M7-A3, 1993, 13 (25), Villanova, PA., USA.
33. Foroumadi, A.; Emami, S.; Pournourmohammadi, S.; Kharazmi, A.; Shafiee, A. Eur. J. Med. Chem., 2005, 40, 1346-1350.
34. İkizler, A.; Demirbas, N.; İkizler, A. A. J. Heterocycl. Chem., 1996, 33, 1765-1769.
35. Galic, N.; Peric, B.; Kojic-Prodic, B.; Cimerman, Z. J. Mol. Struct. 2001, 559, 187-194.
36. Wyrzykiewicz, E.; Prukah, D. J. Heterocycl. Chem. 1998, 35, 381-387.
37. McKelvy, L. M.; Britt, R. T.; Davis, B. L.; Gillie, J. K.; Graves, B. F.; Lentz, L. A. Anal. Chem., 1998, 70, 119R-117R.
38. Salgın-Göksen, U.; Gokhan-Kelekci, N.; Goktas, O.; Köysal, Y.; Kılıc, E.; Isık, S.; Aktay, G.; Ozalp, M. Bioorganic & Medicinal Chemistry, 2007, 15, 5738-5751.
39. Gudasi, K. B.; Patil, M. S.; Vadavi, R. S.; Shenoy, R. V.; Patil, S. A. Transition Metal Chemistry, 2006, 31, 986-991.
40. Dugave, C.; Demange, L. Chem. Rev., 2003, 103, 2475-2532.
41. Rostom, S. A. F.;Ashour, H.M. A.;Abd El Razik, H.A.; Abd El Fattah, H.; El-Din, N.N. Bioorganic & Medicinal Chemistry, 2009, 17, 2410-2422.
42. Bektaş, B.; Karaali, N.; Şahin, D.; Demirbaş, A.; Karaoglu, S. A.; Demirbaş, N. Molecules, 2010, 15, 2427-2438.
43. Demirbaş, A. Turk. J. Chem., 2004, 28, 311-323.

APA	BAYRAK H, DEMİRBAŞ A, BEKTAŞ H, Alpay Karaoğlu Ş, DEMİRBAŞ N (2010). Synthesis and antimicrobial activities of some new 1,2,4-triazole derivatives. , 835 - 846.
Chicago	BAYRAK Hacer,DEMİRBAŞ Ahmet,BEKTAŞ Hakan,Alpay Karaoğlu Şengül,DEMİRBAŞ NESLİHAN Synthesis and antimicrobial activities of some new 1,2,4-triazole derivatives. (2010): 835 - 846.
MLA	BAYRAK Hacer,DEMİRBAŞ Ahmet,BEKTAŞ Hakan,Alpay Karaoğlu Şengül,DEMİRBAŞ NESLİHAN Synthesis and antimicrobial activities of some new 1,2,4-triazole derivatives. , 2010, ss.835 - 846.
AMA	BAYRAK H,DEMİRBAŞ A,BEKTAŞ H,Alpay Karaoğlu Ş,DEMİRBAŞ N Synthesis and antimicrobial activities of some new 1,2,4-triazole derivatives. . 2010; 835 - 846.
Vancouver	BAYRAK H,DEMİRBAŞ A,BEKTAŞ H,Alpay Karaoğlu Ş,DEMİRBAŞ N Synthesis and antimicrobial activities of some new 1,2,4-triazole derivatives. . 2010; 835 - 846.
IEEE	BAYRAK H,DEMİRBAŞ A,BEKTAŞ H,Alpay Karaoğlu Ş,DEMİRBAŞ N "Synthesis and antimicrobial activities of some new 1,2,4-triazole derivatives." , ss.835 - 846, 2010.
ISNAD	BAYRAK, Hacer vd. "Synthesis and antimicrobial activities of some new 1,2,4-triazole derivatives". (2010), 835-846.

APA	BAYRAK H, DEMİRBAŞ A, BEKTAŞ H, Alpay Karaoğlu Ş, DEMİRBAŞ N (2010). Synthesis and antimicrobial activities of some new 1,2,4-triazole derivatives. Turkish Journal of Chemistry, 34(6), 835 - 846.
Chicago	BAYRAK Hacer,DEMİRBAŞ Ahmet,BEKTAŞ Hakan,Alpay Karaoğlu Şengül,DEMİRBAŞ NESLİHAN Synthesis and antimicrobial activities of some new 1,2,4-triazole derivatives. Turkish Journal of Chemistry 34, no.6 (2010): 835 - 846.
MLA	BAYRAK Hacer,DEMİRBAŞ Ahmet,BEKTAŞ Hakan,Alpay Karaoğlu Şengül,DEMİRBAŞ NESLİHAN Synthesis and antimicrobial activities of some new 1,2,4-triazole derivatives. Turkish Journal of Chemistry, vol.34, no.6, 2010, ss.835 - 846.
AMA	BAYRAK H,DEMİRBAŞ A,BEKTAŞ H,Alpay Karaoğlu Ş,DEMİRBAŞ N Synthesis and antimicrobial activities of some new 1,2,4-triazole derivatives. Turkish Journal of Chemistry. 2010; 34(6): 835 - 846.
Vancouver	BAYRAK H,DEMİRBAŞ A,BEKTAŞ H,Alpay Karaoğlu Ş,DEMİRBAŞ N Synthesis and antimicrobial activities of some new 1,2,4-triazole derivatives. Turkish Journal of Chemistry. 2010; 34(6): 835 - 846.
IEEE	BAYRAK H,DEMİRBAŞ A,BEKTAŞ H,Alpay Karaoğlu Ş,DEMİRBAŞ N "Synthesis and antimicrobial activities of some new 1,2,4-triazole derivatives." Turkish Journal of Chemistry, 34, ss.835 - 846, 2010.
ISNAD	BAYRAK, Hacer vd. "Synthesis and antimicrobial activities of some new 1,2,4-triazole derivatives". Turkish Journal of Chemistry 34/6 (2010), 835-846.