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Design, Synthesis, and Antibacterial Activity of Novel Carbacephems Publisher



Moosavimovahedi AA1 ; Yen CF2 ; Chamani J3 ; Khodarahmi GA4 ; Saboury AA1 ; Hakimelahi GH1, 4, 5, 6
Authors
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Authors Affiliations
  1. 1. Institute of Biochemistry and Biophysics, University of Tehran, Tehran, Iran
  2. 2. Department of Chemical and Materials Engineering, Ta Hwa Institute of Technology, Chiunglin, Hsinchu 30703, Taiwan
  3. 3. Department of Biology, Faculty of Science, Islamic Azad University-Mashad Branch, Mashhad, Iran
  4. 4. Department of Medicinal Chemistry, Faculty of Pharmacy, Isfahan University of Medical Sciences, Isfahan, Iran
  5. 5. Institute of Chemistry, Academia Sinica, Taipei, 115, Taiwan
  6. 6. TaiGen Biotechnology, Taipei, 114, 138 Shin Ming Rd., Neihu Dist., Taiwan

Source: Letters in Drug Design and Discovery Published:2006


Abstract

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. © 2006 Bentham Science Publishers Ltd.
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