Nuclear analogs of β-lactam antibiotics. XIII. Structure activity relationships in the isocephalosporin series

The general synthetic scheme to nuclear analogs of cephalosporins described in previous papers of this series is reviewed and the synthesis of a series of sidechain derivatives is given. Thus, systems of the following type were formed: carbacephems (A), 2-isocephems (B), N-2-isocephems (C), and O-2-...

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Published in:Canadian journal of chemistry 1980-12, Vol.58 (23), p.2508-2523
Main Authors: Doyle, Terrence W, Douglas, James L, Belleau, Bernard, Conway, Terry T, Ferrari, C. F, Horning, Donald E, Lim, Gary, Luh, Bing-Yu, Martel, Alain, Menard, Marcel, Morris, L. R, Misiek, Martin
Format: Article
Language:English
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Summary:The general synthetic scheme to nuclear analogs of cephalosporins described in previous papers of this series is reviewed and the synthesis of a series of sidechain derivatives is given. Thus, systems of the following type were formed: carbacephems (A), 2-isocephems (B), N-2-isocephems (C), and O-2-isocephems (D). The invitro microbiological activity of these compounds (with appropriate side-chains attached) is given, with comparison to analogous cephalosporins. Systems of type A, B, and C were only prepared with a 3-H or CH 3 substituent and had modest antibacterial activity. The O-2-isocephems (D) were prepared with a wide variety of sidechains at 3 and 7 and were found to have biological activity quite comparable to the cephalosporins. A more detailed biological examination (both invitro and invivo) of the O-2-isocephem analog ( 19 i) of cephalothin was made.
ISSN:0008-4042
1480-3291
DOI:10.1139/v80-402