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- W2007254959 abstract "Replacement of a sulphur atom by an oxygen at the 1-position of the cephem nucleus generally resulted in fourfold to sixteenfold increase of antibacterial activity in each pair of the structural congeners. However, the increased antibacterial activity caused by the replacement was accompanied by instability to β-lactamase to some extent, which was due presumably to the increased chemical reactivity of the β-lactam ring system. The aim of the research effort is to confer β-lactamase stability and expand the Gram-negative spectrum. Two types of substituents have been demonstrated to protect 1-oxacephem from enzymic hydrolysis and their protecting effects were specifically related to the types of β-lactamases derived from Gram-negative bacteria: the 7β-malonylamino function is specific to cephalosporinase and the 7α-methoxy group to penicillinase. The complementary effect of these substituents was clearly demonstrated. This line of studies led us to prepare the clinical candidate 6059-S, which possessed widely expanded antibacterial spectra against Gramnegative bacteria including indole-positive Proteus , Enterobacter , Sarratia marcescen s, Pseudomonas aeruginosa and Bacteroides fragilis." @default.
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- W2007254959 date "1980-05-16" @default.
- W2007254959 modified "2023-09-25" @default.
- W2007254959 title "Structural requirements for antibacterial activity and β-lactamase stability of 7β-arylmalonylamino-7α-methoxy-1-oxacephems" @default.
- W2007254959 doi "https://doi.org/10.1098/rstb.1980.0041" @default.
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