4-Adamantyl-(2-(arylidene)hydrazinyl)thiazoles as potential antidiabetic agents: experimental and docking studies

To develop an efficient and cost-effective antidiabetic agent. A simple and convenient synthetic strategy was used to prepare 4-adamantyl-(2-(arylidene)hydrazinyl)thiazoles. Fifteen newly established structures of 4-adamantyl-(2-(arylidene)hydrazinyl)thiazoles were tested for their α-amylase, antiglycation and antioxidant activities. Almost all tested compounds showed excellent α-amylase inhibition. Compounds and exhibited the highest potency, with IC values of 16.34 ± 2.67 and 16.64 ± 1.12 μM, respectively. Compounds and exhibited comparable antiglycation potential with the standard, aminoguanidine. The antioxidant potential of compound was found to be excellent, with an IC value of 28.19 ± 0.2563 μM. The binding interactions of compound (binding energy = -8.833 kcal/mol) with human pancreatic α-amylase identified as a potent α-amylase inhibitor. Enrichment of established structures with more electron-donating functionalities may assist/lead to the development of more potent antidiabetic drugs. Diabetes is one of the major causes of death in the present era. To combat damaging processes associated with diabetes, called glycation and oxidation, we prepared a series of compounds called 4-adamantyl-(2-(arylidene)hydrazinyl)thiazoles. The established structures were tested for their antidiabetic potential. The compounds 4-adamantyl-(2-(4-chlorobenzylidene)hydrazinyl)thiazole and 4-adamantyl-(2-(2-chlorobenzylidene)hydrazinyl)thiazole showed the highest potency. The compounds 4-adamantyl-(2-(4-bromobenzylidene)hydrazinyl)thiazole and 4-adamantyl-(2-(2-hydroxybenzylidene)hydrazinyl)thiazole exhibited comparable antiglycation potential. The antioxidant potential of compound 4-adamantyl-(2-(3-nitrobenzylidene)hydrazinyl)thiazole was found to be excellent. A further test was used to check toxicity and all compounds were found to be biocompatible. We also investigated, through docking studies, the way in which these compounds interact with the human proteins albumin and pancreatic α-amylase. Novel adamantylhydrazinylthiazoles were prepared, characterized and evaluated for their antiglycation/antioxidant potential and amylase inhibition. Cytotoxicity of the compounds was checked and molecular docking was performed to check their binding interactions with HSA and HPA.