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Coumarin sulfonates: New alkaline phosphatase inhibitors; in vitro and in silico studies.

Authors :
Salar U
Khan KM
Iqbal J
Ejaz SA
Hameed A
Al-Rashida M
Perveen S
Tahir MN
Source :
European journal of medicinal chemistry [Eur J Med Chem] 2017 May 05; Vol. 131, pp. 29-47. Date of Electronic Publication: 2017 Mar 06.
Publication Year :
2017

Abstract

A library of coumarin derived sulfonyl esters (1-38) was synthesized by reacting various hydroxy coumarins with different alkyl and aryl sulfonyl chlorides. All compounds were evaluated for their potential to inhibit alkaline phosphatases (hTNAP and hIAP). Most of the compounds were found to be inhibitors of APs. Compound 20 was found to be the most active hIAP inhibitor (IC <subscript>50</subscript>  = 1.11 ± 0.15 μM), whereas, compound 13 was found to be the most active hTNAP inhibitor (IC <subscript>50</subscript>  = 0.58 ± 0.17 μM). Detailed structure activity relationship studies (SAR), and molecular docking studies were carried out to identify structural elements necessary for AP inhibition, in addition to rationalize most probable binding site interaction of the inhibitors with the AP enzymes.<br /> (Copyright © 2017 Elsevier Masson SAS. All rights reserved.)

Details

Language :
English
ISSN :
1768-3254
Volume :
131
Database :
MEDLINE
Journal :
European journal of medicinal chemistry
Publication Type :
Academic Journal
Accession number :
28288318
Full Text :
https://doi.org/10.1016/j.ejmech.2017.03.003