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 [J].
Alp, Mehmet ;
Goker, Hakan ;
Brun, Reto ;
Yildiz, Sulhiye .
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 [J].
Amir, M ;
Shikha, K .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2004, 39 (06) :535-545
[3]   Synthesis, antioxidant and radical scavenging activities of novel benzimidazoles [J].
Ayhan-Kilcigil, G ;
Ku, C ;
Çoban, T ;
Can-Eke, B ;
Özbey, S ;
Iscan, M .
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2005, 20 (05) :503-514
[4]   Synthesis and antioxidant properties of novel benzimidazole derivatives [J].
Ayhan-Kilcigil, G ;
Kus, C ;
Çoban, T ;
Can-Eke, B ;
Iscan, M .
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2004, 19 (02) :129-135
[5]   Synthesis and antioxidant capacities of some new benzimidazole derivatives [J].
Ayhan-Kilcigil, Guelguen ;
Kus, Canan ;
Ozdamar, Elcin D. ;
Can-Eke, Benay ;
Iscan, Muemtaz .
ARCHIV DER PHARMAZIE, 2007, 340 (11) :607-611
[6]   Antioxidant evaluation protocols: Food quality or health effects [J].
Becker, EM ;
Nissen, LR ;
Skibsted, LH .
EUROPEAN FOOD RESEARCH AND TECHNOLOGY, 2004, 219 (06) :561-571
[7]   LIPID PEROXIDE FORMATION IN RAT BRAIN [J].
BISHAYEE, S ;
BALASUBRAMANIAN, AS .
JOURNAL OF NEUROCHEMISTRY, 1971, 18 (06) :909-+
[8]   ANTIOXIDANT DETERMINATIONS BY THE USE OF A STABLE FREE RADICAL [J].
BLOIS, MS .
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 [J].
BURKE, MD ;
THOMPSON, S ;
ELCOMBE, CR ;
HALPERT, J ;
HAAPARANTA, T ;
MAYER, RT .
BIOCHEMICAL PHARMACOLOGY, 1985, 34 (18) :3337-3345
[10]  
C Ku, 2004, ARCH PHARM RES, V27, P156