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ID: ALA1139933

Journal: Bioorg Med Chem

Title: Synthesis of andrographolide derivatives: a new family of alpha-glucosidase inhibitors.

Authors: Xu HW, Dai GF, Liu GZ, Wang JF, Liu HM.

Abstract: Andrographolide (1), the cytotoxic agent of the plant Andrographis paniculata, was subjected to semi-synthetic studies leading to a series of new derivatives, a novel family of glucosidase inhibitors. Nicotination of 3,19-hydroxyls in 15-alkylidene andrographolide derivatives (9) was favorable to alpha-glucosidase inhibition activity. Among them, 15-p-chlorobenzylidene-14-deoxy-11,12-didehydro-3,19-dinicotinateandrographolide (11c) was a very potent inhibitor against alpha-glucosidase with an IC50 value of 6 microM. However, all compounds concerned for beta-glucosidase showed no inhibition. All compounds synthesized were characterized by the analysis of NMR, IR, HRMS spectra and the stereochemistry of 2 was confirmed by X-ray analysis.

CiteXplore: 17428667

DOI: 10.1016/j.bmc.2007.03.063