Identification of a Novel Series of N-Phenyl-5-[(2phenylbenzimidazol-1-yl)methyl]-1,3,4-oxadiazol-2-amines as Potent Antioxidants and Radical Scavengers

被引:11
作者
Ayhan-Kilcigil, Gulgun [1 ]
Kus, Canan [1 ]
Coban, Tulay [2 ]
Ozdamar, Elcin D. [2 ]
Can-Eke, Benay [2 ]
机构
[1] Ankara Univ, Dept Pharmaceut Chem, Fac Pharm, TR-06100 Ankara, Turkey
[2] Ankara Univ, Dept Toxicol, Fac Pharm, TR-06100 Ankara, Turkey
关键词
Benzimidazoles; DPPH; EROD; Lipid peroxidation; Oxadiazoles; LIPID PEROXIDE FORMATION; ANTIFUNGAL; MECHANISMS;
D O I
10.1002/ardp.201300324
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
In this study, some novel 5-[[2-(phenyl/p-chlorophenyl)-benzimidazol-1-yl]-methyl]-N-substituted phenyl-1,3,4-oxadiazol-2-amine derivatives (28-45) with an oxadiazole ring were synthesized. The antioxidant properties and radical scavenging activities of the compounds were investigated employing various in vitro systems: hepatic microsomal NADPH-dependent inhibition of lipid peroxidation levels, scavenging of DPPH free radicals, and inhibition of microsomal ethoxyresorufin O-deethylase activity (EROD). Compounds 34 and 41 were found to be good scavengers of DPPH radicals (76% and 84%) when compared to BHT (90%). Almost all of the compounds examined were found to possess a good inhibitor effect on the microsomal EROD activity. Moreover, 32 and 41 were more active analogs (97% and 98%) on the microsomal EROD activity than caffeine (85%).
引用
收藏
页码:276 / 282
页数:7
相关论文
共 28 条
  • [1] Synthesis and antiparasitic and antifungal evaluation of 2′-arylsubstituted-1H,1′H-[2,5′]bisbenzimidazolyl-5-carboxamidines
    Alp, Mehmet
    Goker, Hakan
    Brun, Reto
    Yildiz, Sulhiye
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (05) : 2002 - 2008
  • [2] Synthesis and anti-inflammatory, analgesic, ulcerogenic and lipid peroxidation activities of some new 2-[(2,6-dichloroanilino) phenyl]acetic acid derivatives
    Amir, M
    Shikha, K
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2004, 39 (06) : 535 - 545
  • [3] Synthesis, antioxidant and radical scavenging activities of novel benzimidazoles
    Ayhan-Kilcigil, G
    Ku, C
    Çoban, T
    Can-Eke, B
    Özbey, S
    Iscan, M
    [J]. JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2005, 20 (05) : 503 - 514
  • [4] Synthesis and antioxidant properties of novel benzimidazole derivatives
    Ayhan-Kilcigil, G
    Kus, C
    Çoban, T
    Can-Eke, B
    Iscan, M
    [J]. JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2004, 19 (02) : 129 - 135
  • [5] Synthesis and antioxidant capacities of some new benzimidazole derivatives
    Ayhan-Kilcigil, Guelguen
    Kus, Canan
    Ozdamar, Elcin D.
    Can-Eke, Benay
    Iscan, Muemtaz
    [J]. ARCHIV DER PHARMAZIE, 2007, 340 (11) : 607 - 611
  • [6] Antioxidant evaluation protocols: Food quality or health effects
    Becker, EM
    Nissen, LR
    Skibsted, LH
    [J]. EUROPEAN FOOD RESEARCH AND TECHNOLOGY, 2004, 219 (06) : 561 - 571
  • [7] LIPID PEROXIDE FORMATION IN RAT BRAIN
    BISHAYEE, S
    BALASUBRAMANIAN, AS
    [J]. JOURNAL OF NEUROCHEMISTRY, 1971, 18 (06) : 909 - +
  • [8] ANTIOXIDANT DETERMINATIONS BY THE USE OF A STABLE FREE RADICAL
    BLOIS, MS
    [J]. NATURE, 1958, 181 (4617) : 1199 - 1200
  • [9] ETHOXYPHENOXAZONES, PENTOXYPHENOXAZONES, AND BENZYLOXYPHENOXAZONES AND HOMOLOGS - A SERIES OF SUBSTRATES TO DISTINGUISH BETWEEN DIFFERENT INDUCED CYTOCHROMES-P-450
    BURKE, MD
    THOMPSON, S
    ELCOMBE, CR
    HALPERT, J
    HAAPARANTA, T
    MAYER, RT
    [J]. BIOCHEMICAL PHARMACOLOGY, 1985, 34 (18) : 3337 - 3345
  • [10] C Ku, 2004, ARCH PHARM RES, V27, P156