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Bioorg Med Chem. 2008 Nov 15;16(22):9757-63. doi: 10.1016/j.bmc.2008.09.066. Epub 2008 Sep 30.

Synthesis of triazole-linked beta-C-glycosyl dimers as inhibitors of PTP1B.

Author information

1
PPSM, ENS Cachan, CNRS, UniverSud, 61 av President Wilson, F-94230 Cachan, France.

Abstract

Protein tyrosine phosphatase 1B (PTP1B) has emerged as a promising target for type 2 diabetes. We have successfully synthesized dimeric acetylated and benzoylated beta-C-d-glucosyl and beta-C-D-galactosyl 1,4-dimethoxy benzenes or naphthalenes by click chemistry. These compounds were further transformed into the corresponding beta-C-D-glycosyl-1,4-quinone derivatives by CAN oxidation. The in vitro inhibition test showed that dimeric benzoylated beta-C-D-glycosyl 1,4-dimethoxybenzenes or 1,4-benzoquinones were good inhibitors of PTP1B (IC(50): 0.62-0.88 miroM), with no significant difference between gluco and galacto derivatives.

PMID:
18922697
DOI:
10.1016/j.bmc.2008.09.066
[Indexed for MEDLINE]

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