Synthesis, antioxidant and radical scavenging activities of novel benzimidazoles (original) (raw)
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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 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.
Journal of enzyme inhibition and medicinal chemistry, 2005
Some 6-fluoro-5-substituted-benzimidazole derivatives in which indole and 1,1,4,4-tetramethyl-1,2,3,4-tetrahydro-naphthalene groups were attached to the 2-position of the benzimidazole ring were synthesized and tested for antioxidant properties in vitro. Almost all the synthesized compounds at the 10(-3) M concentrations showed superoxide anion scavenging activity. Compounds 5, 3, 9, 4, 17 and 13 have strong inhibitory effects on superoxide anion formation (98%, 93%, 91%, 88%, 85% and 81%, respectively) at 10(-3) M concentration and these results are better than 30 IU of superoxide dismutase (SOD) (76%). Compound 11 is the most effective scavenger of 2,2-diphenyl-1-picrylhydrazyl (DPPH) stable free radical at 10(-3)M (61%) concentration.
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.
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.
Antioxidant and antifungal properties of benzimidazole derivatives
Zeitschrift fur Naturforschung. Section C, Biosciences
Antioxidant and radical scavenging properties of a series of 2-[4-(substituted piperazin-/piperidin-1-ylcarbonyl)phenyl]-1H-benzimidazole derivatives were examined. Free radical scavenging properties of compounds 11-30 and 33 were evaluated for the stable free radical 2,2-diphenyl-1-picrylhydrazyl (DPPH) and superoxide anion radical. In addition the inhibitory effects on the NADPH-dependent lipid peroxidation levels were determined by measuring the formation of 2-thiobarbituric acid reactive substances (TBARS) using rat liver microsomes. Compound 33 which has a p-fluorobenzyl substitutent at position 1 exhibited the strongest inhibition (83%) of lipid peroxidation at a concentration of 10(-3) M, while the nonsubstituted analogue 13 caused 57% inhibition. This result is fairly consistent with the antimicrobial activity results against both Staphylococcus aureus and Candida albicans.
Archives of Pharmacal Research, 2004
Some benzimidazole derivatives namely 1-[(substituted thiocarbamoylhydrazine carbonyl) methyl]-2-phenyl-lH-benzimidazoles (la-13a), N-[(2-phenylbenzimidazol-l-yl methyl)-[1,3,4]thiadiazole-2-yl]-substituted phenyl amines (lb-13b) and 5-(2-phenyl benzimidazol-l-ylmethyl)-4-substituted phenyl-4H-1,2,4-triazole-3-thiones (lc-13c) were synthesized, and their in vitro effects on the rat liver microsomal NADPH-dependent lipid peroxidation (LP) levels were determined. The most active compound 1Oa caused an 84% inhibition of LP at 10 3 M, which is better than that of butylated hydroxytoluene (BHT) (65%).
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.