Repository of Research and Investigative Information

Repository of Research and Investigative Information

Ilam University of Medical Sciences

Novel cyclic thiourea derivatives of aminoalcohols at the presence of AlCl3 catalyst as potent alpha-glycosidase and alpha-amylase inhibitors: Synthesis, characterization, bioactivity investigation and molecular docking studies

Wed Sep 28 22:52:26 2022

(2020) Novel cyclic thiourea derivatives of aminoalcohols at the presence of AlCl3 catalyst as potent alpha-glycosidase and alpha-amylase inhibitors: Synthesis, characterization, bioactivity investigation and molecular docking studies. Bioorganic Chemistry. p. 104216. ISSN 1090-2120 (Electronic) 0045-2068 (Linking)

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Official URL: https://www.ncbi.nlm.nih.gov/pubmed/32911191

Abstract

The article is devoted to the targeted synthesis and study of cyclic thiourea and their various new derivatives as new organic compounds containing polyfunctional group in the molecule. First time the reaction of the corresponding synthesized pyrimidinethione with 1,2-epoxy-3-chlorpropane at the presence of AlCl3 catalyst in 75-80 yield alkyl-1-(3-chloro-2-hydroxypropyl)-4-alkyl-6-phenyl-2-thioxo-1,2,5,6- tetrahydropyrimidine-5-carboxylates. In the next stage, new cyclic thiourea derivatives of aminoalcohols were synthesised from the reaction of chlorinated derivatives of pyrimidinethiones with single amines and their structures were investigated by spectroscopic methods. In this study, a series of novel compounds were tested towards some metabolic enzymes including alpha-glycosidase (alpha-Gly) and alpha-amylase (alpha-Amy) enzymes. Novel compounds showed Kis in ranging of 10.43 +/- 0.94-111.37 +/- 13.25 microM on alpha-glycosidase and IC50 values in ranging of 14.38-106.51 microM on alpha-amylase. The novel cyclic thiourea derivatives of aminoalcohols had effective inhibition profiles against all tested metabolic enzymes. Binding affinity and inhibition mechanism of the most active compounds were detected with in silico studies and have shown that 2-Hydroxypropyl and butan-1-aminium moieties play a key role for inhibition of the enzymes.

Item Type: Article
Creators:
CreatorsEmail
Sujayev, A.UNSPECIFIED
Taslimi, P.UNSPECIFIED
Garibov, E.UNSPECIFIED
Karaman, M.UNSPECIFIED
Mahdi Zangeneh, M.UNSPECIFIED
Keywords: Aminoalchole Cyclic thiourea Enzyme inhibition Epichlorohydrine Molecular docking competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
Divisions:
Page Range: p. 104216
Journal or Publication Title: Bioorganic Chemistry
Journal Index: Pubmed
Volume: 104
Identification Number: https://doi.org/10.1016/j.bioorg.2020.104216
ISSN: 1090-2120 (Electronic) 0045-2068 (Linking)
Depositing User: مهندس مهدی شریفی
URI: http://eprints.medilam.ac.ir/id/eprint/3106

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