Document Report Card

ID: ALA1122813

Journal: J Med Chem

Title: Synthesis and antibacterial activity of 2-[(methoxycarbonyl)methylene]cephalosporins.

Authors: Kim CU, Misco PF, Haynes UJ, McGregor DN.

Abstract: The synthesis and in vitro activities of a series of 2-[(methoxycarbonyl)methylene]-3-cephem-4-carboxylic acids with methyl or acetoxymethyl at the 3-position are described. The key step in the synthesis includes the stereospecific formation of the 2-[(Z)-(methoxycarbonyl)methylene] group by Pummerer rearrangement of the sulfoxides 3a and 3b. It was also possible to isomerize photochemically the C-2 olefin of 4a to its E isomer, 9. The new derivatives exhibited significant in vitro Gram-positive antibacterial activity.

CiteXplore: 6471077

DOI: 10.1021/jm00375a026