國家衛生研究院 NHRI:Item 3990099045/4959

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Title:	Design, synthesis and biological evaluation of novel carbapenems
Authors:	Hakimelahi, GH;Moosavi-Movahedi, AA;Saboury, AA;Osetrov, V;Khodarahmi, GA;Shia, KS
Contributors:	Division of Biotechnology and Pharmaceutical Research
Abstract:	Racemic trans-3-hydroxycarbonyl-6-(phenylacetamido)carbapenem 13 and trans-3-phosphono-6-(phenylacetamido)carbapenem 17 were synthesized. Formation of the carbapenem nuclei in 13 involved an internal Wittig reaction of the corresponding monocyclic β-lactam 10 using NaH in THF. The key step in the transformation of carbapenam 15 to 3-phosphonocarbapenem 17 involved either a decarboxylative-bromination reaction and subsequent elimination or a bromination reaction followed by decarboxylative-elimination. 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.
Date:	2005
Relation:	International Journal of Scientific Research. 2005;14:59-70
Link to:	http://www.cos.uaeu.ac.ae/pdf/irsu/cos_chemistry_ijsru_vol_14.pdf
Appears in Collections:	[Kak-Shan Shia] Periodical Articles

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