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

Autor:	Gary Lim, James L. Douglas, Martin Misiek, Marcel Menard, Leeson R. Morris, Bing Yu Luh, C. F. Ferrari, Alain Martel, Donald E. Horning, Terry T. Conway, Terrence W. Doyle, Bernard Belleau
Rok vydání:	1980
Předmět:	chemistry.chemical_compound Series (mathematics) chemistry medicine.drug_class Stereochemistry Organic Chemistry Antibiotics Cephalosporin medicine Lactam General Chemistry Catalysis
Zdroj:	Canadian Journal of Chemistry. 58:2508-2523
ISSN:	1480-3291 0008-4042
DOI:	10.1139/v80-402
Popis:	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 CH3 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.
Databáze:	OpenAIRE
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