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Mechanochemical Synthesis, in vitro Evaluation and Molecular Docking Studies of 4-Amino-2-arylamino-5-(benzofuran-2-oyl)thiazoles as Antidiabetic Agents

Author(s):

Kallikat N. Rajasekharan*, Vijayan R. Akhila, Maheswari R Priya, Daisy R. Sherin, Girija K. Krishnapriya and Thanathu K. Manojkumar   Pages 1 - 9 ( 9 )

Abstract:


The synthesis of 4-amino-2-arylamino-5-(benzofuran-2-oyl)thiazoles 4a-h, for example of 2,4-diaminothiazole-benzofuran hybrids and an evaluation of their antidiabetic activity, by in vitro and computational methods, are reported. The synthesis of these diaminothiazoles was achieved mechanochemically by a rapid solvent-less method. Their antidiabetic activity was assessed by α-glucosidase and α-amylase inhibition assays. The IC50 value for α-glucosidase inhibition by 4-amino-5- (benzofuran-2-oyl)-2-(4-methoxyphenylamino)thiazole (4d) was found to be 20.04 μM and the IC50 value for α-amylase inhibition, 195.03 μM, whereas the corresponding values for reference acarbose were 53.38 μM and 502.03 μM, respectively. Molecular docking studies at the active sites of α- glucosidase and α-amylase showed that among the diaminothiazoles 4a-h now studied, 4-amino-5- (benzofuran-2-oyl)-2-(4-methoxyphenylamino)thiazole (4d) has the highest D-scores of -8.63 and -8.08 for α-glucosidase and for α-amylase, with binding energies -47.76 and -19.73 kcal/mol, respectively.

Keywords:

Mechanochemical, α-Glucosidase, α-Amylase, Molecular Docking, 2-4-Diaminothiazoles

Affiliation:

University of Kerala, Department of Chemistry, Kariavattom Campus, Thiruvananthapuram, University of Kerala, Department of Chemistry, Kariavattom Campus, Thiruvananthapuram, University of Kerala, Department of Chemistry, Kariavattom Campus, Thiruvananthapuram, IIITM-K, Centre for Computational Modeling and Data Engineering, University of Kerala, Department of Chemistry, Kariavattom Campus, Thiruvananthapuram, IIITM-K, Centre for Computational Modeling and Data Engineering



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