Jump to main content
Jump to site search


Synthesis of novel inhibitors of α-amylase based on thiazolidine-4-one skeleton containing pyrazole moiety and their configurational studies

Abstract

Postprandial hyperglycemia can be controlled by delaying the absorption of glucose resulting from carbohydrate digestion. α-amylase is the initiator of the hydrolysis of polysaccharides, therefore developing α-amylase inhibitors can lead to development of new treatments for metabolic disorders like diabetes mellitus. In the present work, we set out to rationally develop α-amylase inhibitors based on thiazolidine-4-one scaffold. The structure of all these newly synthesized hybrids was confirmed by spectroscopic analysis (IR, 1H-NMR, MS). Appearance of two sets of signals for some protons in 1H NMR revealed the existence of a mixture of 2E,5Z (37.1-42.0% ) and 2Z,5Z isomer (58.4-62.8%) which was further supported by DFT studies. All the newly synthesized compounds have potential inhibitory properties as revealed through in vitro α-amylase inhibition activity. Compound 5a in 100 µg/mL concentration showed remarkable inhibition of 90.04%. In vitro α-amylase inhibition was further supported by docking studies of compound 5a against active site of human pancreatic α-amylase (PDB ID: 2QV4). Docking studies revealed that the bonding interactions found between 5a and human pancreatic α-amylase are similar to those responsible for α-amylase inhibition by acarbose.

Back to tab navigation
Please wait while Download options loads

Supplementary files

Publication details

The article was received on 18 Feb 2017, accepted on 12 May 2017 and first published on 16 May 2017


Article type: Research Article
DOI: 10.1039/C7MD00080D
Citation: Med. Chem. Commun., 2017, Accepted Manuscript
  •   Request permissions

    Synthesis of novel inhibitors of α-amylase based on thiazolidine-4-one skeleton containing pyrazole moiety and their configurational studies

    D. P. Kumar, M. Duhan, K. Kadyan, J. Sindhu, S. Kumar and H. Sharma, Med. Chem. Commun., 2017, Accepted Manuscript , DOI: 10.1039/C7MD00080D

Search articles by author