RESUMEN
The synthesis of 1 beta-methylcarbapenems having a ROCH2 substituent at the 2-position is described. Their in vitro antibacterial activity and DHP-I susceptibilities are presented.
Asunto(s)
Antibacterianos/síntesis química , Antibacterianos/farmacología , Relación Estructura-Actividad , beta-LactamasRESUMEN
The antibiotic efrotomycin (I), C59H88N2O20, was isolated from cultures of Nocardia lactamdurans as an amorphous yellow powder. Mass spectral and NMR analyses show that the compound is a glycoside of the known antibiotic aurodox (II), C44H62N2O12. Ozonolysis and hydrolysis of I produced the disaccharide V, 6-deoxy-4-O-(6-deoxy-2,4-di-O-methyl-alpha -L-mannopyranosyl)-3-O-methyl-beta-D-allopyranose. This disaccharide is attached to the 4-hydroxyl group of the hexahydropyran substructure of aurodox via a beta-linkage to C-1 of the allose.
Asunto(s)
Antibacterianos , Espectroscopía de Resonancia Magnética , Espectrometría de Masas , Conformación Molecular , PiridonasRESUMEN
delta 1-Thienamycin (2), a double-bond isomer of thienamycin, was prepared by isomerizing N-[[(p-nitrobenzyl)oxy]-carbonyl]thienamycin p-nitrobenzyl ester (5b) with DBU in Me2SO followed by hydrogenolysis of the protecting groups. When evaluated in a disc-diffusion antibacterial assay, delta 1-thienamycin was found to be essentially devoid of activity. The lack of antibacterial activity was ascribed to a chemically less reactive beta-lactam amide bond than that found in thienamycin.