Semisynthetic beta-lactam antibiotics IX. Synthesis and antibacterial activity of 7-[2- (2-aminothiazol-4-yl) -2-sulfoacetamido]-cephalosporanic acid and its derivatives
Minami, I.; Akimoto, H.; Kondo, M.; Nomura, H.
Chemical and Pharmaceutical Bulletin 31(2): 482-489
ISSN/ISBN: 0009-2363 PMID: 6883583 DOI: 10.1248/cpb.31.482
Novel 2-(2-aminothiazol-4-yl)-2-sulfoacetyl cephalosporins were synthesized by 2 routes: acylation of 7-aminocephalosporanic acid or its analogs with an active derivative of 2-(2-aminothiazol-4-yl)-2-sulfoacetic acid, and side chain sulfonation of .gamma.-chloroacetoacetyl cephalosporins with SO3-dioxane and subsequent thiazole ring formation by treatment with thiourea. The cephalosporin with 4-carbamoylpyridiniomethyl at the 3-position showed a potent antipseudomonal activity but had poor activity against other gram-negative bacteria; the cephalosporin with 1-methyltetrazol-5-ylthiomethyl at the 3-position showed a broad spectrum activity, but caused no inhibition of Pseudomonas aeruginosa.