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Benzothiazole benzimidazole (S)-isothiazolidinone derivatives as protein tyrosine phosphatase-1B inhibitors.

Abstract：

:Benzothiazole benzimidazole (S)-isothiazolidinone ((S)-IZD) derivatives 5 were discovered through a peptidomimetic modification of the tripeptide (S)-IZD protein tyrosine phosphatase 1B (PTP1B) inhibitor 1. These derivatives are potent, competitive, and reversible inhibitors of PTP1B with improved caco-2 permeability. An X-ray co-crystal structure of inhibitor 5/PTP1B at 2.2A resolution demonstrated that the benzothiazole benzimidazole forms bi-dentate H-bonds to Asp48, and the benzothiazole interacts with the surface of the protein in a solvent exposed region towards the C-site. The design, synthesis, and SAR of this novel series of benzothiazole benzimidazole containing (S)-IZD inhibitors of PTP1B are presented herein.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Sparks RB,Polam P,Zhu W,Crawley ML,Takvorian A,McLaughlin E,Wei M,Ala PJ,Gonneville L,Taylor N,Li Y,Wynn R,Burn TC,Liu PC,Combs AP

doi

10.1016/j.bmcl.2006.10.079

subject

Has Abstract

pub_date

2007-02-01 00:00:00

pages

736-40

issue

3

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(06)01252-2

journal_volume

17

pub_type

杂志文章

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