Synthesis, Binding and Docking Studies of Indole‐1,3,4‐Thiadiazole Derivatives As Potent Α‐Amylase and Lox Inhibitors

Author:

Doddagaddavalli Manasa A.1,Katrahalli Umesha2,Joshi Shrinivas D.3,Seetharamappa J.1

Affiliation:

1. Department of Chemistry Karnatak University Dharwad 580 003, Karnataka India

2. PG Department of Chemistry Vijaya College, Basavanagudi Bengaluru 560 004 India

3. Novel Drug Design and Discovery Laboratory Department of Pharmaceutical Chemistry SET's College of Pharmacy Dharwad 580 002, Karnataka India

Abstract

AbstractSeries of indole‐1,3,4‐thiadiazole compounds (IT 17) were synthesized and characterized by FT‐IR, 1H NMR, 13C NMR and ESI‐MS spectral data. Further, the compounds (IT 17) were screened for antidiabetic, antioxidant and anti‐inflammatory activities. Most of these compounds exhibited moderate to good antidiabetic, antioxidant and anti‐inflammatory activities against α‐amylase enzyme, ABTS and lipoxygenase enzyme, respectively. Among these, IT‐1 displayed the better activity compared to that of standard drugs. The mechanism of binding of IT‐1, IT‐5 and IT‐6 with a transporter protein, human serum albumin was investigated by fluorescence spectroscopic and circular dichroism studies. These compounds quenched the intrinsic fluorescence intensity of HSA and moderate binding was evident from the values of binding constants which are in the order of 105 M−1. The molecular docking studies of the compounds were performed against human pancreatic alpha‐amylase in complex with montbretin A (PDB ID: 4W93). The studied compounds interacted with amino acid residues (ASP197, GLU240 and TYR151) which were similar to that of the reference drug, acarbose. The ADME properties of designed compounds were studied using SwissADME software. All the compounds obeyed Lipinski's rule of five. All the compounds showed low or non‐toxicity towards different toxicity classes as analyzed using ProTox‐II online tool.

Publisher

Wiley

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