Synthesis and antioxidant and antimicrobial evaluation of novel 4-substituted-1H-1,2,4-triazole derivatives

Turkish Journal of Chemistry

Volumn 36, Issue 6, 2012, Pages 867-884

  Baytaş, Sultan ^a   Kapçak, Evin ^a   Çoban, Tülay ^b   Özbilge, Hatice ^c  

^a GAZI UNIVERSITY   (Turkey)

^b ANKARA UNIVERSITY   (Turkey)

^c ERCIYES UNIVERSITY   (Turkey)

Author keywords

1,2,4 triazole; Antimicrobial activity; DPPH; Indole; Lipid peroxidation; Superoxide

Indexed keywords

EID: 84870856821     PISSN: 13000527     EISSN: 13036130     Source Type: Journal    
DOI: 10.3906/kim-1202-62     Document Type: Article

References (52)

1. D'Autreaux, B.; Toledano, M. B. Nature Reviews Molecular Cell Biology 2007, 8, 813-824.
2. Uchida, K., Free Rad. Biol. Med. 2000, 28, 1685-1696.
3. Cadenas, E.; Davies, K. J. A., Free Rad. Biol. Med. 2000, 29, 222-230.
4. Remans, P. H.; van Oosterhout, M.; Smeets, T. J.; Sanders, M.; Frederiks, W. M.; Reedquist, K. A.; Tak, P. P.; Breedveld, F. C; van Laar, J. M.; Arthritis Rheum. 2005, 52, 2003-2009.
5. Surapaneni, K. M.; Venkataramana, G.; Indian J. Med. Sci. 2007, 61, 9-14.
6. Waris, G.; Ahsan, H.; J. Carcinog. 2006, 5, 14-21.
7. Klika, K.; Saleem, A.; Sinkkonen, J.; Kahkonen, M.; Loponen, J.; Tahtinen, P.; Pihlaja, K. Arkivoc 2004, 8, 83-105.
8. Balakrishna, A.; Veera, M.; Reddy, N.; Nayak, K.; Manjunath, M.; Reddy, C., Chem. Pharm. Bull. 2008, 56, 1486-1489.
9. Saracoglu, N. Top. Heterocycl. Chem. 2007, 11, 1-61.
10. Suzen, S. Top. Heterocycl. Chem. 2007, 11, 145-178.
11. Antosiewicz, J.; Damiani, E.; Jassem, W.; Wozniak, M.; Orena, M.; Greci, L. Free Rad. Biol. Med. 1997, 22, 249-255.
12. Dong, Y.; Venkatchalam, T. K.; Narla, R. K.; Trieu, V. N.; Sudbeck, E.A.; Uckun, F. Free Rad. Biol. Med. 2000, 10, 87-90.
13. Olgen, S.; Coban, T. Arch. Pharm. Pharm. Med. Chem. 2002, 7, 331-338.
14. Olgen, S.; Coban, T. Biol. Pharm. Bull. 2003, 26, 736-738.
15. Suzen, S.; Bozkaya, P.; Coban, T.; Nebioglu, D. J. Enzym. Inhib. Med. Chem. 2006, 21, 405-411.
16. Mathew, V.; Keshavayya, J.; Vaidya, V.P., Giles. D. Eur. J. Med. Chem. 2004, 42, 823-840.
17. Raafat M. S. Arkivoc 2006, 9, 59-112.
18. Brodie, A. M.; Schwarzel, W. C.; Shaikh, A. A.; Brodie, H. J. Endocrinol. 1977, 100, 1684-1688.
19. Bekircan, O.; Ozen, T.; Gumrukcuoglu, N.; Bektas, H. Z. Naturfor. 2008, 63, 548-554.
20. Kus, C.; Ayhan-Kilcigil, G.; Can-Eke, B.; Iscan, M., Arch. Pharm. Res. 2004, 27, 156-163.
21. Ayhan-Kilcigil, G.; Kus, C.; Coban, T.; Can-Eke, B.; Iscan, M. J. Enzym. Inhib. Med. Chem. 2004, 19, 129-135.
22. Ayhan-Kilcigil, G.; Kus, C.; Coban, T.; Can-Eke, B.; Ozbey, S.; Iscan, M. J. Enzym. Inhib. Med. Chem. 2005, 20, 503-514.
23. Kus, C.; Ayhan-Kilcigil, G.; Ozbey, S.; Kaynak, F. B.; Kaya, M.; Coban, T.; Can-Eke, B. Bioorg. Med. Chem. 2008, 16, 4294-4303.
24. Andreadou, I.; Tsantili-Kakoulidou, A.; Spyropoulou, E.; Siatra, T. Chem. Pharm. Bull. 2003, 51, 1128-1131.
25. Avila, M.; Said, N.; Ojcius D. M. Microbes and Infections 2008, 10, 942-947.
26. Al-Qawasmeh, R. A.; Huesca, M.; Nedunuri, V.; Peralta, R.; Wright, J.; Lee, Y.; Young, A. Bioorg. Med. Chem. Lett. 2010, 20, 3518-3520.
27. Oh, K.; Mar, W.; Kim, S.; Kim, J.; Oh, M.; Kim, J.; Shin, D.; Sim, C. J.; Shin, J. Bioorg. Med. Chem. Lett. 2005, 15, 4927-4931.
28. Yamamoto, Y.; Kurazono, M. Bioorg. Med. Chem. Lett. 2007, 17, 1626-1628.
29. Ryu, C. K.; Lee, J. Y.; Park, R. E.; Ma, M. Y.; Nho, J. H. Bioorg. Med. Chem. Lett. 2007, 17, 127-131.
30. Tiwari, R. K.; Singh, D.; Singh, J.; Yadav, V.; Pathak, A. K.; Dabur, R.; Chhillar, A. K.; Singh, R.; Sharma, G. L.; Chandraa, R.; Vermaa, A. K. Bioorg. Med. Chem. Lett. 2006, 16, 413-416.
31. Mahboobi, S.; Eichhorn, E.; Popp, A.; Sellmer, A.; Elz, S.; M?ollmann, U. Eur. J. Med. Chem. 2006, 41, 176-191.
32. Sellitto, G.; Faruolo, A.; Caprariis, P.; Altamura, S.; Paonessa, G.; Ciliberto, G. Bioorg. Med. Chem. 2010, 18, 6143-6148.
33. Raval, J. P.; Patel, H. V.; Patel, P. S.; Desai K. R. Journal of Saudi Chemical Society 2010, 14, 417-421.
34. Al-Soud, Y. A.; Al-Dweri, M. N.; Al-Masaudi, N. A. Il Farmaco 2004, 59, 775-783.
35. Isloor, A. M.; Kalluraya, B.; Shetty, P. Eur. J. Med. Chem. 2009, 44, 3784-3787.
36. Tsotinis, A.; Varvaresou, A.; Calogeropoulou, T.; Papastaikoudi, T.; Tiligada, A. Arzneim.-Forsch./Drug Res. 1997, 47, 307-310.
37. Kaplancikli, Z.; Turan-Zitouni, G.; ? Ozdemir, A.; Revial, G. Eur. J. Med. Chem. 2008, 43, 155-159.
38. Alemany, A.; Fernandez, A. E.; Hernandez, S. R.; Anales de Quimica 1975, 71, 406-411.
39. McCord, J. M.; Fridovich, I. J. Biol. Chem. 1969, 244, 6049-6055.
40. Blois, M. S. Nature 1958, 181, 1199-1200.
41. Mihara, M.; Uchiyama, M.; Fukuzawa, K. Biochem. Med. 1980, 23, 302-311.
42. Clinical and Laboratory Standards Institute (CLSI) (formerly NCCLS), P.S.f.A.S.T., 16th Informational Supplement. CLSI M100-S16, Clinical and Laboratory Standards Institute, 940 West Valley Road, Wayne, Pennsylvania, USA, 2006.
43. Clinical and Laboratory Standards Institute (CLSI) (formerly NCCLS), R.M.f.B.D.A.S.T.Y., Approved standard, M27-A, Clinical and Laboratory Standards Institute, 940 West Valley Road, Wayne, Pennsylvania, USA, 2006.
44. Tsotinis, A.; Afroudakis, P. A.; Davidson, K.; Prashar, A.; Sugden, D. J. Med. Chem. 2007, 50, 6436-6440.
45. Zheng, X.; Li, Z.; Wang, Y.; Chen, W.; Huang, Q.; Liu, C.; Song, G. J. Fluorine Chem. 2003, 123, 163-169.
46. Moise, M.; Sunel, V.; Profire, L.; Popa, M.; Desbrieres, J.; Peptu, C. Molecules 2009, 14, 2621-2631.
47. Shi, W.; Qian, X.; Zhang, R.; Song, G. J. Agric. Food Chem. 2001, 49, 124-130.
48. Amir, M.; Shikha, K. Eur. J. Med. Chem. 2004, 39, 535-545.
49. Turan-Zitouni, G., Sivac, M.; Kilic, F. S.; Erol, K. Eur. J. Med. Chem. 2001, 36, 685-689.
50. Das, S.; Falchi, M.; Bertelli, A.; Maulik, N.; Das, D. K. Arzneim.-Forsch./Drug Res. 2006, 56, 700-706.
51. Riccioni, G.; Bucciarelli, T.; Mancini, B.; Di Ilio, C.; Capra, V.; D'Orazio, N.; Expert. Opin. Investig. Drugs 2007, 16, 25-32.
52. Andreadou, I.; Tasouli, A.; Iliodromitis, E.; Tsantili-Kakoulidou, A.; Papalois, A.; Siatra, T.; Kremastinos, D. Eur. J. Pharm. 2002, 453, 271-277.