Synthesis and evaluation of the alpha-glucosidase inhibitory activity of 3-[4-(phenylsulfonamido)benzoyl]-2H-1-benzopyran-2-one derivatives

Shaojie Wang; Jufang Yan; Xiaoyan Wang; Zhuo Yang; Fengwei Lin; Tingjian Zhang

doi:10.1016/j.ejmech.2009.12.031

Synthesis and evaluation of the alpha-glucosidase inhibitory activity of 3-[4-(phenylsulfonamido)benzoyl]-2H-1-benzopyran-2-one derivatives

Eur J Med Chem. 2010 Mar;45(3):1250-5. doi: 10.1016/j.ejmech.2009.12.031. Epub 2009 Dec 22.

Authors

Shaojie Wang¹, Jufang Yan, Xiaoyan Wang, Zhuo Yang, Fengwei Lin, Tingjian Zhang

Affiliation

¹ Key Laboratory of New Drugs Design and Discovery of Liaoning Province, Shenyang Pharmaceutical University, 103 Culture Road, Shenhe District, Shenyang 110016, China. [email protected]

PMID: 20045223
DOI: 10.1016/j.ejmech.2009.12.031

Abstract

In the course of studies directed toward the discovery of novel non-sugar alpha-glucosidase inhibitors for the treatment of diabetes, a series of 3-[4-(phenylsulfonamido)benzoyl]-2H-1-benzopyran-2-one derivatives was synthesized and evaluated as alpha-glucosidase inhibitors. Most compounds showed good inhibitory activity with IC(50) values ranging from 0.0645 microM to 26.746 microM. 7-Hydroxy-6-methoxy-3-[4-(4-methylphenylsulfonamido)benzoyl]-2H-1-benzopyran-2-one 7u manifested the most potent inhibitory activity with an IC(50) value of 0.0645 microM.

MeSH terms

Benzopyrans / chemical synthesis
Benzopyrans / chemistry
Benzopyrans / pharmacology
Coumarins / chemical synthesis*
Coumarins / chemistry
Coumarins / pharmacology*
Drug Design
Enzyme Inhibitors* / chemical synthesis
Enzyme Inhibitors* / pharmacology
Glycoside Hydrolase Inhibitors*
Inhibitory Concentration 50
Molecular Structure
Sulfonamides / chemical synthesis
Sulfonamides / chemistry
Sulfonamides / pharmacology

Substances

7-hydroxy-6-methoxy-3-(4-(4-methylphenylsulfonamido)benzoyl)-2H-1-benzopyran-2-one
Benzopyrans
Coumarins
Enzyme Inhibitors
Glycoside Hydrolase Inhibitors
Sulfonamides