Synthesis and structure-activity relationships of a new series of cephalosporins, BMY-28142 and related compounds.
نویسندگان
چکیده
The synthesis of a series of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-oxyiminoacetamido] -3-ammoniomethyl-3-cephems is described. Variations of an oxyimino moiety in the 7-side chain and a quaternary ammonium moiety in the 3-side chain were examined and structure-activity relationships studied. BMY-28142, the 3-(N-methylpyrrolidinio)methyl derivative of the 7-alpha-methoxyimino series of cephalosporins, exhibited broad antimicrobial activity against both Gram-positive and Gram-negative bacteria including Pseudomonas aeruginosa.
منابع مشابه
In vitro studies of BMY-28142, a new broad-spectrum cephalosporin.
BMY-28142 was compared with other broad-spectrum antibiotics against gram-positive cocci and gram-negative bacilli. BMY-28142 was highly active against all gram-negative bacilli and especially against Enterobacter cloacae, Serratia marcescens, and Morganella morganii. Its in vitro activity suggests that BMY-28142 should prove to be useful for the treatment of gram-negative bacillary infections.
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Strains of Escherichia coli, Enterobacter aerogenes, and Enterobacter cloacae that were resistant to ceftazidime (MIC greater than 16 micrograms/ml) but susceptible to BMY 28142 (MIC less than 4 micrograms/ml) were found to contain higher levels of beta-lactamase activity (50- to 3,340-fold) than control strains of the corresponding species. Ceftazidime was at least as resistant as BMY 28142 to...
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Cephalosporinases of Enterobacter cloacae and Citrobacter freundii were responsible for resistance to newer cephalosporins such as cefotaxime and ceftazidime but not BMY-28142. Interaction of these cephalosporins including hydrolysis, binding, inhibition, and inactivation with cephalosporinases from E. cloacae GN7471 and C. freundii GN7391 were studied. BMY-28142 was much more stable against th...
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Compared with four beta-lactam antibiotics and amikacin, BRL 36650 and BMY-28142 were the most active against 509 Enterobacteriaceae, including cefotaxime-resistant isolates and resistant laboratory mutants. BRL 36650 was more active than aztreonam, ceftazidime, and BMY-28142 against Acinetobacter spp., Pseudomonas aeruginosa, and other Pseudomonas spp.; all strains were inhibited by 2 microgra...
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Thirty-one Cephalosporin compounds were modeled using the multivariate image analysis and applied to the quantitative structure activity relationship (MIA-QSAR) approach. The acid dissociation constants (pKa) of cephalosporins play a fundamental role in the mechanism of activity of cephalosporins. The antimicrobial activity of cephalosporins was related to their first pKa by different models. B...
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عنوان ژورنال:
- The Journal of antibiotics
دوره 39 8 شماره
صفحات -
تاریخ انتشار 1986