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Coumarin sulfonates: New alkaline phosphatase inhibitors; in vitro and in silico studies.
- 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.)
- Subjects :
- Alkaline Phosphatase metabolism
Coumarins chemical synthesis
Coumarins chemistry
Dose-Response Relationship, Drug
Enzyme Inhibitors chemical synthesis
Enzyme Inhibitors chemistry
Humans
Models, Molecular
Molecular Structure
Structure-Activity Relationship
Sulfonic Acids chemical synthesis
Sulfonic Acids chemistry
Alkaline Phosphatase antagonists & inhibitors
Coumarins pharmacology
Enzyme Inhibitors pharmacology
Sulfonic Acids pharmacology
Subjects
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