Semisynthetic cephalosporins with alpha-oximino acid side chains. The preparation and coupling of 4-acylamino-alpha-oximinobenzeneacetic acids and 1,2-dihydro-6-methyl-alpha-oximino-2-oxo-3-pyridineacetic acid to 7-aminocephalosporanic acid.
A series of 4-acylamino-alpha-oximinobenzeneacetic acids, and 1,2-dihydro-6-methyl-alpha-oximino-2-oxo-3-pyridineacetic acid were prepared and coupled to 7-aminocephalosporanic acid and its 3'-(1-methyltetrazol-5-yl)thiolo analogue. Several coupling methods and oxime protecting groups were thoroughly examined. The best coupling procedure employed dimethylchloroformiminium chloride, and the tetrahydropyranyl (THP) group was selected for oxime protection. The cephalosporins prepared were tested and compared to cefuroxime and cefotaxime. The corresponding alpha-keto acids, and O-methyl oximes were also examined.
D000813:Anilides / Q000138:chemical synthesis / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D002511:Cephalosporins / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D007098:Imino Acids / Q000138:chemical synthesis / Q000494:pharmacology; D011728:Pyridones / Q000138:chemical synthesis / Q000494:pharmacology; D013329:Structure-Activity Relationship
D000813:Anilides; D002511:Cephalosporins; D007098:Imino Acids; D011728:Pyridones