Novel 3-O-acyl mesquitol analogues as free-radical scavengers and enzyme inhibitors: synthesis, biological evaluation and structure-activity relations...

Basic Information

ID: ALA1136168

Journal: Bioorg Med Chem Lett

Title: Novel 3-O-acyl mesquitol analogues as free-radical scavengers and enzyme inhibitors: synthesis, biological evaluation and structure-activity relationship.

Authors: Jagadeeshwar Rao R, Tiwari AK, Kumar US, Reddy SV, Ali AZ, Rao JM.

Abstract: A new isomer of mesquitol (2,3-trans-3',4',7,8-tetrahydroxyflavan-3-ol) was isolated from Dichrostachys cinerea in excellent yields. It has shown free-radical scavenging property and alpha-glucosidase inhibitory activities but, it could not display xanthine oxidase inhibitory property. However, it was observed that acylation of 3-OH group significantly enhanced the alpha-glucosidase inhibition and displayed xanthine oxidase inhibitory potential. The structure activity relationship revealed that the degree of lipophilicity played a major role in improving enzyme inhibitory activities. A positive correlation was observed between enzyme inhibitory potential and acyl chain length (upto C-16) of aliphatic esters.

CiteXplore: 12873513

DOI: 10.1016/s0960-894x(03)00494-3

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