In this study, we prepared some new oxadiazolyl benzimidazole derivatives and investigated their antioxidant properties by determination of microsomal NADPH-dependent inhibition of lipid peroxidation levels (LP assay) and microsomal ethoxyresorufin O-deethylase activity (EROD assay). Some of these compounds 20, 23 had slightly inhibitory effects (28%) on the lipid peroxidation levels at 10(-3 )M concentration lower than standard BHT (65%). 5-[2-(Phenyl)-benzimidazol-1-yl-methyl]-2-mercapto-[1,3,4]-oxadiazole 16 was found to be more active than caffeine on the ethoxyresorufin O-deethylase activity with an IC(50 )value of 2.0 6 10(-4 )M.
In this study, two new series of 2-amino-1,3,4-oxadiazoles and 5-aryl-1,3,4-oxadiazoles carrying a benzimidazole moiety were synthesized. The antioxidant properties of these compounds were investigated in vitro by the determination of the microsomal NADPH-dependent inhibition of lipid peroxidation levels (LP), the microsomal ethoxyresorufin O-deethylase activity (EROD), and DPPH radical scavenger effects. Among the tested compounds, 2-[(2-(4-chlorophenyl)-1H-benzo[d]imidazole-1-yl)methyl]-5-(4-fluorophenyl)-1,3,4-oxadiazole (9) was found to be the most active compound in all three in vitro systems.
Our approach was to synthesize and examine the antioxidant properties of some new 2-[2-(4-chlorophenyl)benzimidazole-1-yl]-N-(2-arylmethyleneamino) acetamide (1-18) and 2-[2-(4-chlorophenyl)benzimidazole-1-yl]-N-(4-oxo-2-aryl-thiazolidine-3-yl)acetamide (1t-18t) derivatives. Their in vitro effects on rat liver microsomal NADPH-dependent lipid peroxidation levels (LP assay) and microsomal ethoxyresorufin O-deethylase activities (EROD assay) were determined. The free radical scavenging properties of the compounds were also examined in vitro determining the interaction of 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical. The compounds showed significant effects in the above tests. Reactive oxygen species (ROS) and reactive nitrogen species (RNS) are generated in aerobic organisms as part of the normal physiological and metabolic processes or from exogenous factors and agents. These ROS are capable of damaging a wide range of essential macromolecules (membrane lipids, proteins, nucleic acids). The damages by ROS are directly or indirectly implicated in the pathogenesis of various disorders such as cardiovascular diseases, Alzheimer's and other neurodegenerative diseases,
Some novel 2-(substitutedbenzylthio)-5-((2-(4-substitutedphenyl)-1 H -benzo[d]imidazol-1-yl)methyl)-1,3,4oxadiazoles (5-12) and 2-(2-(4-chlorophenyl)-1 H -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.
Amaç: Bu çalışma, 4-(sübstitüe benziliden)-2-(sübstitüefenil)oksazol-5(4H)-on (E1-E10) türevlerini sentezlemek, yapılarını aydınlatmak ve antioksidan etkilerini araştırmaktır. Gereç ve Yöntemler: Oksazol-5(4H)-on türevleri iki yolak ile sentezlenmiştir. Yeni hippürik asit türevlerini (7-13) elde etmek için, glisin ve açillenmiş uygun benzoik asitler kullanıldı ve bu bileşiklerin (7-13) uygun benzaldehitler ile kondensasyon reaksiyonu ile de sonuç ürünlere (E1-E10) ulaşılmıştır. Bu ürünler etil asetat/n-hekzan solvan sistemi kullanılarak kolon kromatografisi ile temizlenmiştir. Tüm bileşikler için 1 H and 13 C-nükleer manyetik rezonans, mass spektrometresi (ESI-MS), elemental analiz yöntemleri kullanılarak yapıları tanımlanmıştır. Lipid peroksidasyon inhibisyonu ve karaciğer sitokrom P450 bağımlı Etoksirezorfin-O-deetilaz (EROD) enzimi üzerindeki etkileri sıçanlarda in vitro olarak tespit edildi. Bulgular: Mikrozomal EROD aktivitesi üzerinde en aktif analog, EROD aktvitesini %89 ile inhibe eden E3'tür, benzer şekilde 10-3 M konsantrasyonda spesifik inhibitör kafeinden (%85) daha iyi idi. Sonuç: Bu çalışmanın bulguları, E3 gibi sentezlenen bileşiklerin, önemli antioksidan aktivite sergilediğini göstermektedir. Anahtar kelimeler: Oksazolidinonlar, sentez, antioksidan aktivite, lipid peroksidasyon, EROD aktivite Objectives: To synthesize and characterize 4-(substituted benzylidene)-2-(substituted phenyl)oxazol-5(4H)-one derivatives (E1-E10), and evaluate them for antioxidant activity. Materials and Methods: Required oxazole-5(4H)-one derivatives were synthesized in two steps to obtain novel hippuric acid derivatives (7-13); glycine and acylated appropriate benzoic acid derivatives were used and then, final compounds were obtained with condensation of 7-13 with appropriate benzaldehydes (E1-E10). These products were purified by column chromatography using ethyl acetate/n-hexane as eluent. All the compounds were unequivocally characterized using the combination of 1 H and 13 C-nuclear magnetic resonance, mass spectrometry (ESI-MS), and elemental analysis. The inhibition of lipid peroxidation and its effects on hepatic cytochrome P450-dependent ethoxyresorufin-O-deethylase (EROD) enzyme were determined in rats in vitro. Results: The most active analogue on the microsomal EROD activity was E3 which inhibited the microsomal EROD activity (89%) and was similarly better than that of the specific inhibitor caffeine (85%) at 10-3 M concentration. Conclusion:The findings of this study indicate that the synthesized compounds, such as E3, display significant antioxidant activity.
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