Structure--activity relationships in cephalosporins prepared from penicillins. 2. Analogues of cephalexin substituted in the 3-methyl group

A previously outlined general procedure for preparing various 3-substituted cephalosporins from the penicillin nucleus has been used, with modifications where required, to prepare a series of analogues of cephalexin with various substituents in the 3-methyl group. The 3-substituents most conducive t...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1977-08, Vol.20 (8), p.1086-1090
Main Authors: Brain, E G, Eglington, A J, James, B G, Nayler, J H, Osborne, N F, Pearson, M J, Smale, T C, Southgate, R, Tolliday, P, Basker, M J, Mizen, L W, Sutherland, R
Format: Article
Language:English
Subjects:
Animals
Bacteria - drug effects
Cephalexin - analogs & derivatives
Cephalexin - blood
Cephalexin - chemical synthesis
Cephalexin - pharmacology
Mice
Microbial Sensitivity Tests
Staphylococcus aureus - drug effects
Structure-Activity Relationship
Time Factors
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Summary:A previously outlined general procedure for preparing various 3-substituted cephalosporins from the penicillin nucleus has been used, with modifications where required, to prepare a series of analogues of cephalexin with various substituents in the 3-methyl group. The 3-substituents most conducive to broad-spectrum antibacterial activity were 3-pyridylmethyl and m- or p-carboxybenzyl. The compounds were only poorly absorbed by the oral route in mice, but the 3-(carboxybenzyl) compounds gave more prolonged useful serum levels than the usual cephalosporins.
ISSN:0022-2623
DOI:10.1021/jm00218a019