Nuclear analogs of β-lactam antibiotics. XIII. Structure activity relationships in the isocephalosporin series
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Abstract
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 (19i) of cephalothin was made.
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