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Azolylthioacetamides as a potent scaffold for the development of metallo-β-lactamase inhibitors.

Abstract：

:In an effort to develop new inhibitors of metallo-β-lactamases (MβLs), twenty-eight azolylthioacetamides were synthesized and assayed against MβLs. The obtained benzimidazolyl and benzioxazolyl substituted 1-19 specifically inhibited the enzyme ImiS, and 10 was found to be the most potent inhibitor of ImiS with an IC50 value of 15 nM. The nitrobenzimidazolyl substituted 20-28 specifically inhibited NDM-1, with 27 being the most potent inhibitor with an IC50 value of 170 nM. Further studies with 10, 11, and 27 revealed a mixed inhibition mode with competitive and uncompetitive inhibition constants in a similar range as the IC50 values. These inhibitors resulted in a 2-4-fold decrease in imipenem MIC values using E. coli cells producing ImiS or NDM-1. While the source of uncompetitive (possibly allosteric) inhibition remains unclear, docking studies indicate that 10 and 11 may interact orthosterically with Zn2 in the active site of CphA, while 27 could bridge the two Zn(II) ions in the active site of NDM-1 via its nitro group.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Xiang Y,Chang YN,Ge Y,Kang JS,Zhang YL,Liu XL,Oelschlaeger P,Yang KW

doi

10.1016/j.bmcl.2017.10.038

subject

Has Abstract

pub_date

2017-12-01 00:00:00

pages

5225-5229

issue

23

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(17)31032-6

journal_volume

27

pub_type

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