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Design, Synthesis, and Antibacterial Activity of Novel Carbacephems

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Syntheses of (±)-cis-3-hydroxycarbonyl-7-(phenylacetamido)carbacephem (10), (±)-cis-3- methoxycarbonyl-7-(phenylacetamido)carbacephem (11), (±)-cis-2-chloro-3-hydroxycarbonyl-7-(phenylacetamido) carbacephem (14), and (±)-cis-2-chloro-3-methoxycarbonyl-7-(phenylacetamido)carbacephem (15) were accomplished. These four heretofore undescribed compounds 10, 11, 14, and 15 showed notable activity against Staphylococcus aureus FDA 209P, Escherichia coli ATCC 39188, Pseudomonas aeruginosa 1101-75, Klebsiella pneumoniae NCTC 418 as well as the β-lactamase producing organisms E. coli A9675, P. aeruginosa 18S-H and methicillin-resistant organism S. aureus 95. The electronic activation of lactam moieties of 11 and 15 enhanced remarkably their antibacterial activity relative to those of the 10 and 14. The chlorine atom in 14 and 15, acting as an effective leaving group, also resulted in an increment in the biological activity in comparison with those of the parent carbacephemes 10 and 11. The mode of action related to 14 and 15 can be explained by a non-classical [1,4]-elimination process.

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Keywords: Cephalosporin; antibacterial; antibiotic; b-Lactam; b-Lactamase; carbacephem

Document Type: Research Article

Affiliations: TaiGen Biotechnology, 138 Shin Ming Rd., Neihu Dist., Taipei, Taiwan 114, R. O. C.

Publication date: March 1, 2006

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  • Letters in Drug Design & Discovery publishes original letters on all areas of rational drug design and discovery including medicinal chemistry, in-silico drug design, combinatorial chemistry, high-throughput screening, drug targets, and structure-activity relationships. The emphasis will be on publishing quality papers very rapidly. Letters will be processed rapidly by taking full advantage of Internet technology for both the submission and review of manuscripts. The journal is essential reading to all pharmaceutical scientists involved in research in drug design and discovery.
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