Synthesis and antibacterial activity of 2-[(methoxycarbonyl)methylene]cephalosporins
- 1 September 1984
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 27 (9) , 1225-1229
- https://doi.org/10.1021/jm00375a026
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.Keywords
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