123151-20-2Relevant academic research and scientific papers
3-Sulfonyl-1-carba-1-dethiacephems
Crowell, Thomas A.,Halliday, Basil D.,McDonald, John H.,Indelicato, Joseph M.,Pasini, Carol E.,Wu, Ernie C. Y.
, p. 2436 - 2442 (2007/10/02)
The stability of the 1-carba-1-dethiacephalosporin framework has allowed the synthesis of a range of 3-sulfonyl-1-carba-1-dethiacephems unavailable for a variety of reasons in the cephem arena.The known p-nitrobenzyl 7β-(phenylacetamido)-3-oxy>-1-carba-1-dethia-3-cephem-4-carboxylate served as a precursor to this series of compounds.Displacement of the enol triflate with various sulfinates in acetonitrile or DMF and deprotection of the intermediates led to 7β-amino>-3--1-carba-1-dethia-3-cephem-4-carboxylic acids.The 3-sulfonyl-1-carba-1-dethiacephems display potent activity against both Gram-positive and Gram-negative bacteria.The following MIC's (μg/mL) for the 3-cyclopropyl sulfone are representative: Staphylococcus aureus = 4, Streptococcus pyogenes = 1, Haemophilus influenzae = 0.25, Escherichia coli = 0.03, Enterobacter cloacae = 0.25, Proteus rettgeri = 0.25.The excellent in vitro antibacterial activity of this series indicates the potential of the carbacephalosporin framework for exploring substituents which are unknown or which produce unstable cephems.
