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Design, synthesis, and evaluation of alpha-ketoheterocycles as class C beta-lactamase inhibitors.

Abstract：

:A series of specific alpha-ketoheterocycles (benzoxazole, thiazole, imidazole, tetrazole, and thiazole-4-carboxylate) has been synthesized in order to assess their potential as beta-lactamase inhibitors. The syntheses were achieved either by construction of the heterocycle (benzoxazole) from an appropriate alpha-hydroxyimidate, followed by oxidation of the alcohol, or by direct reaction of methyl phenaceturate with a lithiated heterocycle. The properties of these compounds in aqueous solution are described and their inhibitory activity against beta-lactamases assessed. They did inhibit the class C beta-lactamase of Enterobacter cloacae P99 but not the TEM beta-lactamase. The most effective inhibitor of the former enzyme (K(i)=0.11 mM) was 5-(phenylacetylglycyl) tetrazole, probably because it is an anion at neutral pH. Interpretation of the results was aided by computational models of the tetrahedral adducts. Most of the compounds also inhibited alpha-chymotrypsin but not porcine pancreatic elastase.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Kumar S,Pearson AL,Pratt RF

doi

10.1016/s0968-0896(01)00107-9

subject

Has Abstract

pub_date

2001-08-01 00:00:00

pages

2035-44

issue

8

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(01)00107-9

journal_volume

9

pub_type

杂志文章

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