3-[(1,2,3-Thiadiazol-5-ylthio)methyl]cephalosporins.
The syntheses of ten 3-](1,2,3-thiadiazol-5-ylthio)methyl]cephalosporins, made by displacement of the 3'-acetoxy group by the novel thiol derivatives, potassium 1,2,3-thiadiazole-5-thiolate and dipotassium 1,2,3-thiadiazole-4-carboxylate-5-thiolate, are described. Several of the compounds showed good in vitro antibacterial activity against both Gram-positive and Gram-negative organisms. The subcutaneous in vivo activities against Staphylococcus aureus were generally less than that of cafazolin. Four of the compounds were administered orally and all were active; the 7 beta-(thiophen-2-acetamido) and 7 beta-(D-2-amino-2-phenylacetamido)-3-[(1,2,3-thiadiazol-5-ylthio)methyl] compounds were equally active by either route, with a PD50 of ca. 1 mg/kg.
D000818:Animals; D002511:Cephalosporins / Q000138:chemical synthesis* / Q000494:pharmacology; D004926:Escherichia coli / Q000187:drug effects; D007711:Klebsiella pneumoniae / Q000187:drug effects; D051379:Mice; D011514:Proteus vulgaris / Q000187:drug effects; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D013203:Staphylococcal Infections / Q000188:drug therapy; D013297:Streptococcus pyogenes / Q000187:drug effects
D002511:Cephalosporins