Direct introduction of a formamido group into the 7 alpha (6 alpha)-position of cephalosporins (penicillins).
A novel direct introduction of a formamido group into the 7 alpha (6 alpha)-position of cephalosporins (penicillins) was achieved by treatment of 7 beta (6 beta)-[(3,5-di-tert-butyl-4-oxo-2,5-cyclohexadien-1- ylidene)methylimino]cephem (penam) esters with N,N-bis(trimethylsilyl)formamide, followed by deblocking with Girard reagent T to give the corresponding 7 alpha (6 alpha)-formamido-7 beta (6 beta)-amino derivatives. Three 7 alpha-formamidocephalosporins were prepared by the conventional N-acylation of 7 alpha-formamidocephem. All of them were resistant to beta-lactamases, showing similar MIC values against both of a pair of a beta-lactamase-producing strain and the corresponding non or low-producing strain of the same species of bacteria, when tested on Staphylococcus aureus, Klebsiella pneumoniae, Escherichia coli, Proteus mirabilis, Proteus vulgaris, Morganella morganii, Enterobacter cloacae and Citrobacter freundii.
Kamachi
H
H
Bristol-Myers Research Institute, Ltd., Tokyo Research Center, Japan.
Okita
T
T
Yamasaki
T
T
Naito
T
T
D001419:Bacteria / Q000187:drug effects*; D002511:Cephalosporins / Q000138:chemical synthesis* / Q000494:pharmacology; D055598:Chemical Phenomena; D002621:Chemistry; D002851:Chromatography, High Pressure Liquid; D005559:Formamides; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010406:Penicillins / Q000138:chemical synthesis* / Q000494:pharmacology; D013055:Spectrophotometry, Infrared
D002511:Cephalosporins; D005559:Formamides; D010406:Penicillins