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Carbapenem-Based Prodrugs. Design, Synthesis, and Biological Evaluation of Carbapenems Publisher Pubmed



Hakimelahi GH1, 2, 3, 5 ; Moosavimovahedi AA1 ; Saboury AA1 ; Osetrov V2 ; Khodarahmi GA3 ; Shia KS4
Authors
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Authors Affiliations
  1. 1. Inst. of Biochemistry and Biophysics, University of Tehran, Tehran, Iran
  2. 2. Institutes of Chem. and Biomed. Sci., Academia Sinica, Taipei 115, Taiwan
  3. 3. Department of Medicinal Chemistry, Faculty of Pharmacy, Isfahan Univ. of Medical Sciences, Isfahan, Iran
  4. 4. Div. Biotech. Pharmaceutical Res., National Health Research Institutes, Taipei 114, Taiwan
  5. 5. TaiGen Biotechnology, Taipei 114, 138 Shin Ming Road, Taiwan

Source: European Journal of Medicinal Chemistry Published:2005


Abstract

Syntheses of racemic trans-3-hydroxycarbonyl-6-(phenylacetamido)carbapenem (13), trans-3-phosphono-6-(phenylacetamido)carbapenem (17), and β-lactam based prodrugs 19 and 22 were accomplished. Carbapenem 13 was found to possess antibacterial activity, comparable with imipenem (+)-3, against Staphylococcus aureus FDA 209P, S. aureus 95, Escherichia coli ATCC 39188, Klebsiella pneumoniae NCTC 418, Pseudomonas aeruginosa 1101-75, P. aeruginosa 18S-H, and Xanthomonas maltophilia GN 12873. Like imipenem ((+)-3), carbapenem 13 was not stable to X. maltophilia oxyiminocephalosporinase type II. Its phosphonate analog 17, however, was neither a significant antibacterial agent nor a good β-lactamase inhibitor. Chemical combinations of trans carbapenem 13 with cis carbapenem 6 (compound 19) as well as clavulanic acid (20) with cis carbapenem 6 (compound 22) via a tetrachloroethane linker exhibited remarkable activity against β-lactamase producing microorganisms in vitro. © 2005 Elsevier SAS. All rights reserved.
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