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Non-transpeptidase binding arylthioether β-lactams active against Mycobacterium tuberculosis and Moraxella catarrhalis.

Bioorganic & medicinal chemistry (2015-01-01)
Tim N Beck, Dina Lloyd, Rostislav Kuskovsky, Jeanette Minah, Kriti Arora, Balbina J Plotkin, Jacalyn M Green, Helena I Boshoff, Clifton Barry, Jeffrey Deschamps, Monika I Konaklieva
ABSTRACT

The prevalence of drug resistance in both clinical and community settings as a consequence of alterations of biosynthetic pathways, enzymes or cell wall architecture is a persistent threat to human health. We have designed, synthesized, and tested a novel class of non-transpeptidase, β-lactamase resistant monocyclic β-lactams that carry an arylthio group at C4. These thioethers exhibit inhibitory and cidal activity against serine β-lactamase producing Mycobacterium tuberculosis wild type strain (Mtb) and multiple (n=8) β-lactamase producing Moraxella catarrhalis clinical isolates.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
2-Azetidinone, 98%
Sigma-Aldrich
Chloroform-d, 99.8 atom % D, contains 0.03 % (v/v) TMS
Sigma-Aldrich
Acetone-d6, "100%", 99.96 atom % D
Sigma-Aldrich
Chloroform-d, ≥99.8 atom % D, contains 0.5 wt. % silver foil as stabilizer, 0.03 % (v/v) TMS
Sigma-Aldrich
Chloroform-d, "100%", 99.96 atom % D, contains 0.5 wt. % silver wire as stabilizer
Sigma-Aldrich
Acetone-d6, 99.9 atom % D, contains 0.03 % (v/v) TMS
Sigma-Aldrich
Chloroform-d, "100%", 99.96 atom % D, contains 0.03 % (v/v) TMS
Sigma-Aldrich
Acetone-d6, 99.5 atom % D
Sigma-Aldrich
Acetone-d6, 99.9 atom % D, contains 1 % (v/v) TMS
Sigma-Aldrich
Acetone-d6, 99.9 atom % D
Sigma-Aldrich
Acetone-d6, 99.9 atom % D
Sigma-Aldrich
Chloroform-d, 99.8 atom % D, contains 1 % (v/v) TMS
Sigma-Aldrich
Acetone-d6, 99.9 atom % D
Sigma-Aldrich
Chloroform-d, "100%", 99.96 atom % D
Sigma-Aldrich
Chloroform-d, 99.8 atom % D, contains 0.1 % (v/v) TMS
Sigma-Aldrich
Chloroform-d, 99.8 atom % D
Sigma-Aldrich
Chloroform-d, ≥99.8 atom % D, anhydrous
Sigma-Aldrich
Chloroform-d, 99.8 atom % D, contains 0.05 % (v/v) TMS
Sigma-Aldrich
Chloroform-d, ≥99.8 atom % D, contains 0.5 wt. % silver foil as stabilizer
Sigma-Aldrich
Acetone-d6, ≥99.9 atom % D, contains 0.03 % (v/v) TMS
Sigma-Aldrich
Acetone-d6, 99.9 atom % D
Sigma-Aldrich
Acetone-d6, "100%", 99.96 atom % D