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Paper | Special issue | Vol 30, No. 1, 1990, pp.567-581
Published online, 1st January, 1970
DOI: 10.3987/COM-89-S65
1-Oxacephems with the Thienamycin-Type Side Chain(1). Synthesis and Antibacterial Activity of 7α-[(1R)-1-Hydroxyethl]1-1oxacephems Bearing Electron-Withdrawing Groups

Masayuki Murakami, Tsutomu Aoki, and Wataru Nagata*

*Shionogi Research Laboratories, Shionogi & Co. Ltd., Fukushima-ku, Osaka 553-0002, Japan

Abstract

1-Oxacephem derivatives, 2a-d, bearing the hydroxyethyl group at C and some electron-withdrawing groups at C3 were synthesized and tested for antibacterial activity. It was found that some of these compounds, in particular, 7α-hydroxyethyl-3-cyano-1-oxazephem 2d, exhibited antibacterial activity, although the potency was low. Some 7α-hydroxyethyl-2-oxo-1-oxacephems, 1a,b, were also prepared and found biologically inactive.