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Bioorg Med Chem Lett. 1999 Feb 22;9(4):529-32.

Synthesis and biological evaluation of alpha,alpha-difluorobenzylphosphonic acid derivatives as small molecular inhibitors of protein-tyrosine phosphatase 1B.

Author information

1
School of Pharmacy, Tokyo University of Pharmacy & Life Science, Horinouchi, Hachioji, Japan.

Abstract

A series of alpha,alpha-difluorobenzylphosphonic acids having a hydrophobic functional group were prepared via the Stille coupling reaction from halogenated alpha,alpha-difluorobenzylphosphonates. Evaluation of inhibitory activity toward protein tyrosine phosphatase (PTP 1B) revealed that the ethynyl, phenylethynyl and (E)-styryl groups on the benzene nuclei increased the inhibitory activity of alpha,alpha-difluorobenzylphosphonic acid. Inhibitory activities significantly increased upon introducing both (E)-styryl and bis-methylsulfonamide functional groups onto the benzene nuclei of alpha,alpha-difluorobenzylphosphonic acid.

PMID:
10098656
DOI:
10.1016/s0960-894x(99)00027-x
[Indexed for MEDLINE]

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