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.

Autor: Domagala JM, Haskell TH, Showalter HD
Jazyk: angličtina
Zdroj: The Journal of antibiotics [J Antibiot (Tokyo)] 1981 Nov; Vol. 34 (11), pp. 1447-55.
DOI: 10.7164/antibiotics.34.1447
Abstrakt: 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.
Databáze: MEDLINE