Synthesis and antimicrobial properties of substituted beta-aminoxypropionyl penicillins and cephalosporins.
Some beta-aminoxypropionyl penicillins (3) and cephalosporins (4 and 5), planned on the basis of the hypothesis that the (methyleneaminoxy)methyl group (greater than C = NOCH2) could be a "bioisoster" of either aryls or other aromatic groups, were synthesized and assayed for their antimicrobial properties. Compounds 3-5, tested on Gram-positive and Gram-negative bacteria, both sensitive to enzyme inactivation and otherwise, exhibited an activity trend that was not substantially different from that of the corresponding phenylacetamido derivatives taken as terms of comparison.
Balsamo
A
A
Istituto di Chimica Farmaceutica, Facoltà di Farmacia, Università di Pisa, Italy.
Broccali
G
G
Lapucci
A
A
Macchia
B
B
Macchia
F
F
Orlandini
E
E
Rossello
A
A
D000667:Ampicillin / Q000494:pharmacology; D002439:Cefotaxime / Q000494:pharmacology; D002506:Cephalexin / Q000494:pharmacology; D002511:Cephalosporins / Q000138:chemical synthesis / Q000494:pharmacology*; D055598:Chemical Phenomena; D002621:Chemistry; D006090:Gram-Negative Bacteria / Q000187:drug effects*; D006094:Gram-Positive Bacteria / Q000187:drug effects*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D010400:Penicillin G / Q000494:pharmacology; D010406:Penicillins / Q000138:chemical synthesis / Q000494:pharmacology*
D002511:Cephalosporins; D010406:Penicillins; C028619:phenylacetyl 7-aminodesacetoxycephalosporanic acid; D000667:Ampicillin; C059979:cefaloram; D002439:Cefotaxime; D002506:Cephalexin; D010400:Penicillin G