Yıl: 2015 Cilt: 39 Sayı: 1 Sayfa Aralığı: 42 - 53 Metin Dili: İngilizce İndeks Tarihi: 29-07-2022

Synthesis and evaluation of antioxidant activities of novel 1,3,4-oxadiazole and imine containing 1H-benzimidazoles

Öz:
Abstract: Some novel 2-(substitutedbenzylthio)-5-((2-(4-substitutedphenyl)-1H-benzo[d]imidazol-1-yl)methyl)-1,3,4-oxadiazoles (5--12) and 2-(2-(4-chlorophenyl)-1H-benzo[d]imidazol-1-yl)-N'-(arylmethylene)acetohydrazide derivatives (13--22) were prepared and their in vitro antioxidant properties were investigated by determination of rat liver microsomal NADPH-dependent inhibition of lipid peroxidation (LP) levels and microsomal ethoxyresorufin O-deethylase (EROD) activity. Compound 18 was found to be the most active compound with 100% inhibition on LP level and 92% inhibition on EROD. Compounds 4b, 17, and 19 showed the strongest inhibitory effect (97%) on EROD. The free radical scavenging capacities of the compounds were also tested in vitro determining the interaction of the stable free radical 2,2,diphenyl-1-picrylhydrazyl (DPPH), and compounds 4a and 4b exhibited good antioxidant activities.
Anahtar Kelime:

Konular: Mühendislik, Kimya
Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık
  • Grune, T. Oxidants and Antioxidant Defense Systems. The Handbook of Environmental Chemistry Vol. 2: Reac- tions, Processes; Springer: Berlin, Germany, 2005.
  • Huang, D.; Ou, B.; Prior, R. L. J. Agric. Food Chem. 2005, 53, 1841–1856.
  • Halliwell, B.; Chirico, S. Am. J. Clin. Nutr. 1993, 57, 715S–725S.
  • Cadenas, E.; Packer, L. Handbook of Antioxidants. 2nd edn. Revised and Expanded; Marcel Dekker: New York, NY, USA, 2002.
  • Molyneux, P. Songklanakarin J. Sci. Technol. 2004, 26, 211–219.
  • Kus, C.; Ayhan-Kılcıgil, G.; Can-Eke, B.; Iscan, M. Arch. Pharm. Res. 2004, 27, 156–163.
  • Kus, C.; Ayhan-Kilcigil, G.; Altanlar, N. J. Fac. Pharm. Ankara Univ. 2004, 33, 1–6.
  • Ayhan-Kılcıgil, G.; Kus, C.; Coban, T.; Can-Eke, B.; Iscan, M. J. Enzyme Inhib. Med. Chem. 2004, 19, 129–135.
  • Ayhan-Kilcigil, G.; Kus, C.; Coban, T.; Can-Eke, B.; Ozbey, S.; Iscan, M. J. Enzyme Inhib. Med. Chem. 2005, 20, 503–514.
  • Ayhan-Kilcigil, G.; Kus, C.; Ozdamar, E. D.; Can-Eke, B.; Iscan, M. Arch. Pharm. Chem. Life Sci. 2007, 340, 607–611.
  • Kerimov, I.; Ayhan-Kilcigil, G.; Can-Eke, B.; Altanlar, N.; Iscan, M. J. Enzyme Inhib. Med. Chem. 2007, 22, 696–701.
  • Kus, C.; Ayhan-Kilcigil, G.; Ozbey, S.; Kaynak, F. B.; Kaya, M.; Coban, T., Can-Eke, B. Bioorg. Med. Chem. 2008, 16, 4294–4303.
  • Kus, C.; Ayhan-Kılcıgil, G.; Tuncbilek, M.; Altanlar, N.; Coban, T.; Can-Eke, B.; Iscan, M. L. D. D. D. 2009, 6, 374–379.
  • Ayhan-Kilcigil, G.; Gurkan, S.; Coban, T.; Ozdamar, E. D.; Can-Eke, B. Chem. Biol. Drug. Des. 2012, 76, 869–877.
  • Kerimov, I.; Ayhan-Kılcıgil, G.; Ozdamar, E. D.; Can-Eke, B.; Coban, T.; Ozbey, S.; Kazak, C. Arch. Pharm. Chem. Life Sci. 2012, 345, 549–556.
  • Liu, F.; Luo, X. Q.; Song, B. A.; Bhadury, P. S.; Yang, S.; Jin, L. H.; Xue, W.; Hu, D. Y. Bioorg. Med. Chem. 2008, 16, 3632–3640.
  • Patorski, P.; Wyrzykiewicz, E.; Bartkowiak, G. Journal of Spectroscopy 2013, 2013, 1–12.
  • Kuodis, Z.; Rutavicius, A.; Matijoska, A.; Eicher–Lorka, O. Cent. Eur. J. Chem. 2007, 5, 996–1006. Blois, M. S. Nature 1958, 181, 1199–1200.
  • Burke, M. D.; Thompson, S.; Elcombe, C. R.; Halpert, J.; Haaparanta, T.; Mayer, R. T. Biochem. Pharmacol. 1985, 34, 3337–3345.
  • Iscan, M.; Arinc, E.; Vural, N.; Iscan, M. Y. Comp. Biochem. Physio. 1984, 77C, 177–190. Wills, E. D. Biochem. J. 1966, 99, 667–676.
  • Wills, E. D. Biochem. J. 1969, 113, 333–341.
  • Bishayee, S.; Balasubramanian, A. S. J. Neurochem. 1971, 18, 909–920.
APA ALP A, Kılcıgil G, ÖZDAMAR E, ÇOBAN T, EKE B (2015). Synthesis and evaluation of antioxidant activities of novel 1,3,4-oxadiazole and imine containing 1H-benzimidazoles. , 42 - 53.
Chicago ALP AYŞE SELEN,Kılcıgil Gülgün,ÖZDAMAR Elçin Deniz,ÇOBAN TÜLAY,EKE BİNAY Synthesis and evaluation of antioxidant activities of novel 1,3,4-oxadiazole and imine containing 1H-benzimidazoles. (2015): 42 - 53.
MLA ALP AYŞE SELEN,Kılcıgil Gülgün,ÖZDAMAR Elçin Deniz,ÇOBAN TÜLAY,EKE BİNAY Synthesis and evaluation of antioxidant activities of novel 1,3,4-oxadiazole and imine containing 1H-benzimidazoles. , 2015, ss.42 - 53.
AMA ALP A,Kılcıgil G,ÖZDAMAR E,ÇOBAN T,EKE B Synthesis and evaluation of antioxidant activities of novel 1,3,4-oxadiazole and imine containing 1H-benzimidazoles. . 2015; 42 - 53.
Vancouver ALP A,Kılcıgil G,ÖZDAMAR E,ÇOBAN T,EKE B Synthesis and evaluation of antioxidant activities of novel 1,3,4-oxadiazole and imine containing 1H-benzimidazoles. . 2015; 42 - 53.
IEEE ALP A,Kılcıgil G,ÖZDAMAR E,ÇOBAN T,EKE B "Synthesis and evaluation of antioxidant activities of novel 1,3,4-oxadiazole and imine containing 1H-benzimidazoles." , ss.42 - 53, 2015.
ISNAD ALP, AYŞE SELEN vd. "Synthesis and evaluation of antioxidant activities of novel 1,3,4-oxadiazole and imine containing 1H-benzimidazoles". (2015), 42-53.
APA ALP A, Kılcıgil G, ÖZDAMAR E, ÇOBAN T, EKE B (2015). Synthesis and evaluation of antioxidant activities of novel 1,3,4-oxadiazole and imine containing 1H-benzimidazoles. Turkish Journal of Chemistry, 39(1), 42 - 53.
Chicago ALP AYŞE SELEN,Kılcıgil Gülgün,ÖZDAMAR Elçin Deniz,ÇOBAN TÜLAY,EKE BİNAY Synthesis and evaluation of antioxidant activities of novel 1,3,4-oxadiazole and imine containing 1H-benzimidazoles. Turkish Journal of Chemistry 39, no.1 (2015): 42 - 53.
MLA ALP AYŞE SELEN,Kılcıgil Gülgün,ÖZDAMAR Elçin Deniz,ÇOBAN TÜLAY,EKE BİNAY Synthesis and evaluation of antioxidant activities of novel 1,3,4-oxadiazole and imine containing 1H-benzimidazoles. Turkish Journal of Chemistry, vol.39, no.1, 2015, ss.42 - 53.
AMA ALP A,Kılcıgil G,ÖZDAMAR E,ÇOBAN T,EKE B Synthesis and evaluation of antioxidant activities of novel 1,3,4-oxadiazole and imine containing 1H-benzimidazoles. Turkish Journal of Chemistry. 2015; 39(1): 42 - 53.
Vancouver ALP A,Kılcıgil G,ÖZDAMAR E,ÇOBAN T,EKE B Synthesis and evaluation of antioxidant activities of novel 1,3,4-oxadiazole and imine containing 1H-benzimidazoles. Turkish Journal of Chemistry. 2015; 39(1): 42 - 53.
IEEE ALP A,Kılcıgil G,ÖZDAMAR E,ÇOBAN T,EKE B "Synthesis and evaluation of antioxidant activities of novel 1,3,4-oxadiazole and imine containing 1H-benzimidazoles." Turkish Journal of Chemistry, 39, ss.42 - 53, 2015.
ISNAD ALP, AYŞE SELEN vd. "Synthesis and evaluation of antioxidant activities of novel 1,3,4-oxadiazole and imine containing 1H-benzimidazoles". Turkish Journal of Chemistry 39/1 (2015), 42-53.