Synthesis and antibacterial activity of new arylamido derivatives of 6 beta-aminopenicillanic, 7 beta-aminocephalosporanic and 7 beta-aminodesacetoxycephalosporanic acids.
New semisynthetic penicillins and cephalosporins have been synthesized by acylation of 6 beta-aminopenicillanic, 7 beta-aminocephalosporanic and 7 beta-aminodesacetoxycephalosporanic acids with ortho-substituted aromatic acids, using the method of mixed anhydrides. The chemical structures of the compounds obtained were confirmed by elemental analysis and by IR- and 1H-NMR spectra. Antibacterial activities of the compounds were determined by the macrodilution susceptibility test in brain-heart infusion broth. Test organisms producing beta-lactamases: Bacillus subtilis L2, Bacillus subtilis HB2, Bacillus cereus 30, Bacillus subtilis 6633 ATCC, Bacillus mycoides 924; Staphylococcus aureus 1/45 "Oxford" as Gram-positive bacteria, and Escherichia coli 111, Escherichia coli K12/F-¿lac-/, Escherichia coli K12/F-¿lambda-/, Escherichia coli K12/F-¿lambda-¿lac+/ as Gram-negative bacteria. In general, the derivatives of 6 beta-aminopenicillanic acid were more active than 7 beta-aminocephalosporanic and 7 beta-aminodesacetoxycephalosporanic acid derivatives. Among all the compounds synthesized 6 beta-[4'-(dimethylamino)-azobenzene-2-amido]penicillanic acid and 6 beta-(N-phenylanthranilamido)penicillanic acid showed the best activity and were with the broadest spectrum of action.
Kaloyanov
N
N
Department of Organic Chemistry, University of Chemical Technology and Metallurgy, Sofia, Bulgaria.
Stoyanova
R
R
D001407:Bacillus / Q000187:drug effects; D001419:Bacteria / Q000187:drug effects*; D002511:Cephalosporins / Q000138:chemical synthesis* / Q000494:pharmacology; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D003470:Culture Media; D004926:Escherichia coli / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D010397:Penicillanic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D010406:Penicillins / Q000138:chemical synthesis* / Q000494:pharmacology; D013211:Staphylococcus aureus / Q000187:drug effects
D002511:Cephalosporins; D003470:Culture Media; D010406:Penicillins; D010397:Penicillanic Acid; C004408:aminopenicillanic acid