Synthesis and antioxidant properties of novel benzimidazoles containing substituted indole or 1,1,4,4-tetramethyl-1,2,3,4-tetrahydro-naphthalene fragments (original) (raw)
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Synthesis, antioxidant and radical scavenging activities of novel benzimidazoles
Journal of Enzyme Inhibition and Medicinal Chemistry, 2005
The synthesis and antioxidant evaluation of some novel benzimidazole derivatives (10 -24) are described. Antioxidant properties of the compounds were investigated employing various in vitro systems viz., microsomal NADPH-dependent inhibition of lipid peroxidation (LP), interaction of 2,2-diphenyl-1-picrylhydrazyl (DPPH) and scavenging of superoxide anion radical. Compounds 12 and 13 showed very good antioxidant capacity and were 17-18 -fold more potent than BHT (IC 50 2.3 £ 10 24 M) with 1.3 £ 10 25 M and 1.2 £ 10 25 M IC 50 values, respectively, by interaction of the stable DPPH free radical.
Synthesis and evaluation ofin vitroantioxidant capacities of some benzimidazole derivatives
Journal of Enzyme Inhibition and Medicinal Chemistry, 2006
New, except 1d, melatonin analogue benzimidazole derivatives were synthesized and characterized in the present study. The potential role of melatonin as an antioxidant by scavenging and detoxifying ROS raised the possibility that compounds that are analogous to melatonin can also be used for their antioxidant properties. Therefore the antioxidant effects of the newly synthesized compounds were investigated in vitro by means of their inhibitory effect on hydrogen peroxide-induced erythrocyte membrane lipid peroxidation (EMLP) and on various erythrocyte antioxidant enzymes viz. superoxide dismutase (SOD), catalase (CAT) and glucose-6-phosphate dehydrogenase (G6PD). The synthesized benzimidazole derivatives showed remarkable antioxidant activity in vitro in the H 2 O 2-induced EMLP system. Furthermore their effects on various antioxidant enzymes are discussed and evaluated from the perspective of structure-activity relationships.
Synthesis and evaluation of in vitro antioxidant capacities of some benzimidazole derivatives
Journal of Enzyme Inhibition and Medicinal Chemistry, 2006
New, except 1d, melatonin analogue benzimidazole derivatives were synthesized and characterized in the present study. The potential role of melatonin as an antioxidant by scavenging and detoxifying ROS raised the possibility that compounds that are analogous to melatonin can also be used for their antioxidant properties. Therefore the antioxidant effects of the newly synthesized compounds were investigated in vitro by means of their inhibitory effect on hydrogen peroxide-induced erythrocyte membrane lipid peroxidation (EMLP) and on various erythrocyte antioxidant enzymes viz. superoxide dismutase (SOD), catalase (CAT) and glucose-6-phosphate dehydrogenase (G6PD). The synthesized benzimidazole derivatives showed remarkable antioxidant activity in vitro in the H 2 O 2 -induced EMLP system. Furthermore their effects on various antioxidant enzymes are discussed and evaluated from the perspective of structure-activity relationships.
Synthesis and Antioxidant Activity of Some Novel Benzimidazole Derivatives
Dhaka University Journal of Pharmaceutical Sciences, 2018
A series of 2-substituted-5-methylbenzimidazole derivatives (3a-e) were synthesized by reacting 4-methyl-1,2-phenylenediamine (1) with a number of p-substituted benzaldehydes (2a-e) in moderate yields (25.51-40.21%). The synthesized compounds (3a-e) were characterized by spectroscopic data and were evaluated for antioxidant activity using DPPH free radical scavenging assay. The compounds showed significant antioxidant activity having IC50 value of 1.054-19.05 µg/ml as compared to the standard BHT (26.96 µg/ml).
Synthesis and Antioxidant Properties of New Benzimidazole Derivatives
Politeknik dergisi, 2021
❖ Synthesized compounds were evaluated for their in vitro antioxidant activity. ❖ The structures of synthesized compounds were established on the basis of spectral data. ❖ Enzyme activity was calculated by spectrofluorimetric measurement of the amount of resorufin formed. ❖ The reducing power activities of the compounds were compared with BHT. ❖ Values were the means of three replicates ± Standard deviation.
Synthesis and antioxidant capacities of some new benzimidazole derivatives
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.
Synthesis and Antioxidant Activity of 2-SUBSTITUTED-5-NITRO Benzimidazole Derivatives
International Journal of Pharmacy and Pharmaceutical Sciences, 2016
Objective: This study was conducted to synthesise some 2-substituted-5-nitro benzimidazole derivatives to evaluate their antioxidant activity. Methods: The titled compounds were synthesised by sodium metabisulfite mediated reaction of 4-nitro-1, 2-phenylenediamine with a number of para-substituted benzaldehydes. The antioxidant activity was evaluated by 2, 2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging method. Results: All the compounds exhibited good antioxidant activity having IC50 Conclusion: Among the synthesised compounds, compounds 3a-c have been found to possess the most prominent antioxidant activity which might be attributed due to the presence of chloro, bromo and fluoro substituents in the molecule. The compounds may act as the future lead(s) for the development of potential antioxidant compounds. values in the range of 3.17 to 7.59 µg/ml while that of standard butylated hydroxytoluene (BHT) was 18.42 µg/ml.
International Journal of Pharmacy and Pharmaceutical Sciences, 2017
Objective: This study was conducted to synthesise some 2-substituted-5-nitro benzimidazole derivatives to evaluate their antioxidant activity. Methods: The titled compounds were synthesised by sodium metabisulfite mediated reaction of 4-nitro-1, 2-phenylenediamine with a number of para-substituted benzaldehydes. The antioxidant activity was evaluated by 2, 2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging method. Results: All the compounds exhibited good antioxidant activity having IC50 Conclusion: Among the synthesised compounds, compounds 3a-c have been found to possess the most prominent antioxidant activity which might be attributed due to the presence of chloro, bromo and fluoro substituents in the molecule. The compounds may act as the future lead(s) for the development of potential antioxidant compounds. values in the range of 3.17 to 7.59 µg/ml while that of standard butylated hydroxytoluene (BHT) was 18.42 µg/ml.
Turkish Journal of Chemistry, 2015
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.
Chemical Biology & Drug Design, 2013
2-aryl-1-arylmethyl-1H-benzimidazole derivatives having different side chains on the structure were examined in-vitro for their antioxidant abilities by DPPH (2,2-diphenyl-1-picryl hydrazine) radical scavenging activity, reducing ability, OH radical scavenging activity, inhibition of polyphenol oxidase (PPO) and xanthine oxidase (XO). Overall, with few exceptions, all the 2aryl-1-arylmethyl-1H-benzimidazoles showed moderate biological activity with all parameters examined. The 2-aryl-1-arylmethyl-1H-benzimidazoles were found to be reactive towards DPPH radical and had considerable reducing ability, with significant XO inhibition. With few exceptions, all the compounds under study were found to possess moderate to poor OH radical scavenging activity and inhibited PPO significantly. These findings suggest that, these 2-aryl-1arylmethyl-1H-benzimidazoles can be considered as potential antioxidant and XO inhibitory agents, those might be further, explored for the design of lead antioxidant and anti-gout drug candidates using in vivo trials.