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

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.

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

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.

___

  • 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.
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
  • Yayıncı: TÜBİTAK
Sayıdaki Diğer Makaleler

Synthesis, properties, and electrochemistry of a photochromic compound based on dithienylethene and ProDOT

Melek PAMUK ALGI, Atilla CİHANER, Fatih ALGI

Purification and characterization of NADPH-cytochrome P450 reductase from Lake Van fish liver microsomes and investigation of some chemical and metals' effects on the enzyme activity

Müslüm KUZU, Mehmet ÇİFTCİ

Secondary metabolites from Sambucus ebulus

İrem ATAY, Hasan KIRMIZIBEKMEZ, Ahmet Ceyhan GÖREN, Erdem YEŞİLADA

Deposition of cadmium sulfide and zinc sulfide thin films by aerosol-assisted chemical vapors from molecular precursors

Ashfaque Ahmed MEMON, Malik DILSHAD, Neerish REVAPRASADU

Reduction behavior of fenoxaprop-p-ethyl and its voltammetric determination

Zeki EŞ, İbrahim Hüdai TAŞDEMİR

Electrochemical monitoring of the interaction between mitomycin C and DNA at chitosan--carbon nanotube composite modified electrodes

Pembe Ece CANAVAR, Ece EKŞİN, Arzum ERDEM

Preparation of visible light sensitive nano-sized N-TiO2 photocatalysts and their photocatalytic activity under visible light

Young-Gu KANG, Kwang-Hyeok LEE, Hyun-Sik HAHM

Synthesis and properties of novel magnetic nanoparticles grafted with nitropyridine-substituted calix[4]arene derivative as Cr6+ extractant

Serkan SAYIN, Vildan DOĞAN

Synthesis of methyl 4-(9H-carbazole-9-carbanothioylthio) benzoate: electropolymerization and impedimetric study

Murat ATEŞ, Nesimi ULUDAĞ, Fatih ARICAN, Tolga KARAZEHİR

Synthesis and characterization of substituted benzimidazole Co(II), Fe(II), and Zn(II) complexes and structural characterization of dichlorobis{1-[2-(1-piperidinyl)ethyl]-1H-benzimidazole-KN3} zinc(II)

Hasan KÜÇÜKBAY, Ülkü YILMAZ, Mehmet AKKURT, Orhan BÜYÜKGÜNGÖR