Novel 5-(Arylideneamino)-1H-Benzo[d]imidazole-2-thiols as Potent Anti-Diabetic Agents: Synthesis, In Vitro α-Glucosidase Inhibition, and Molecular Docking Studies

Abstract

A novel series of multifunctional benzimidazoles has been reported as potent inhibitors of α-glucosidase. The procedure relies on the synthesis of 5-amino-1H-benzo[d]imidazole-2-thiol 5 via the multistep reaction through 2-nitroaniline 1, benzene-1,2-diamine 2, 1H-benzo[d]imidazole-2-thiol 3, and 5-nitro-1H-benzo[d]imidazole-2-thiol 4. Further treatment of 5 with aromatic aldehydes 6a−m provided access to the target 5-(arylideneamino)-1H-benzo[d]imidazole-2-thiols 7a−m.The results of the bioactivity assessment revealed all the compounds as excellent inhibitors of the enzyme (IC 50 range: 0.64 ± 0.05 μM to 343.10 ± 1.62 μM) than acarbose (873.34 ± 1.21). Among them, 7i was the most active inhibitor (IC 50 : 0.64 ± 0.05 μM) followed by 7d

“Microwave-Assisted, Solvent Free, One Pot Synthesis of Novel Bioactive Imidazolyl - Pyrazole derivatives catalyzed by Mesolite type Natural Zeolite”

“…Imidazole moiety has been found in number of biological active compounds which have an important medicinal agent. Based on literature surveys imidazole derivatives shows various biological activity such as potent antidiabetic [17], Antimicrobial [18], antifungal [19], anticancer [20,21], antitubercular [22], and anti-HIV [23]. Azo Imidazole derivative shows potential inhibitory action against COVID-19 main proteases [24] and Anti-inflammatory [25].…”

Synthesis of novel coumarin–hydrazone hybrids as α-glucosidase inhibitors and their molecular docking studies

“…The a-glucosidase inhibition assay was performed by using our previous reported methodology. [47][48][49] Experiments were carried out by using phosphate buffer 50 mM, pH. 6.8.…”

Synthesis, Structural Elucidation, In Silico and In Vitro Studies of New Class of Methylenedioxyphenyl-Based Amide Derivatives as Potential Myeloperoxidase Inhibitors for Cardiovascular Protection

“…The present study focuses on the synthesis and application of phytochemical-based organic scaffolds targeting cardiovascular disease risk factors, namely, diabetes and atherosclerosis. Sci-Finder search showed limited scientific reports in the literature for nitro-substituted methylenedioxyphenyl amide-based molecules. , Imidazole, isoindoline, pyridine, triazole, quinoline, and thiosemicarbazone-based heterocyclic derivatives targeting diabetes and atherosclerosis have been reported. − Relatively, a few phytochemical-based scaffolds are used for treating diabetes and atherosclerosis. − Chemically linking phytochemical derivatives to organic molecules improves the efficacy and reduces the toxicity of the drug. Thus, minimal toxicity and maximal effectiveness are anticipated when piperine derivatives are chemically linked to an amine via an amide bond.…”

“… 36 , 37 Imidazole, isoindoline, pyridine, triazole, quinoline, and thiosemicarbazone-based heterocyclic derivatives targeting diabetes and atherosclerosis have been reported. 38 − 43 Relatively, a few phytochemical-based scaffolds are used for treating diabetes and atherosclerosis. 44 − 46 Chemically linking phytochemical derivatives to organic molecules improves the efficacy and reduces the toxicity of the drug.…”