Studies on beta-lactam antibiotics. III. Syntheses and antibacterial activities of new 3-(1,3-dithiolan-2-yl)cephalosporins, YM-22508, YM-16457 and their prodrug-type esters.
نویسندگان
چکیده
The syntheses and biological activities of new 7-beta-[(Z)-2-(2-amino-4-thiazolyl)-2-hydroxy-iminoacetamido]-3-(1 ,3- dithiolan-2-yl)-3-cephem-4-carboxylic acid (YM-22508, 1a), 7-beta-[(Z)-2-(2-amino-4-thiazolyl)-2- methoxyiminoacetamido]-3-(1,3-dithiolan-2-yl)-3-cephem-4-carboxyli c acid (YM-16457, 1d) and their prodrug-type esters are described. Among them, YM-22561 (1c), the 1-acetoxyethyl ester of 1a, showed good in vivo efficacy in mice against infections of Staphylococcus aureus Smith, Streptococcus pyogenes S 23 and Escherichia coli NY-17 and a long plasma T1/2 in mice.
منابع مشابه
Studies on beta-lactam antibiotics. II. Synthesis and antibacterial activity of cephalosporins with substituted 1,3-dithietane directly attached to the C-3 position.
Preparation of cephalosporins bearing a 1,3-dithietane ring attached to the C-3 position using intramolecular rearrangement are described. The diastereoisomers (6a-I and 6a-II) were separated by silica gel column chromatography. These 3-[4-(carbamoyl carboxymethylene)-1,3-dithietane-2-yl]cephems showed comparable activity against Gram-negative bacteria to that of ceftazidime.
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The synthesis and antibacterial activity of 7 beta-[(Z)-2-(2-amino-4-thiazolyl)-2-(hydroxy or alkoxy)iminoacetamido]cephalosporins with various thiadiazolylthiomethyl moieties at the 3-position are discussed. Of the compounds (1a-1e, 7a-7d), 7 beta-[(Z)-2-(2-amino-4-thiazolyl)-2-hydroxyiminoacetamido]-3-[(1,2 ,4- thiadiazol-5-yl)thiomethyl]cephalosporin (1d: FK312) exhibited the highest activit...
متن کاملYM-47522, a novel antifungal antibiotic produced by Bacillus sp. II. Structure and relative stereochemistry.
YM-47522 (1) was isolated from the fermentation broth of Bacillus sp. YL-03709B as an antifungal antibiotic. The structure of 1 was elucidated by spectroscopic analyses. YM-47522 (1) consisted of C13 carboxylic acid amide and cinnamate moieties. The relative stereochemistry was also proposed on the basis of chemical transformation into a 1,3-diol acetonide and its NMR data.
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عنوان ژورنال:
- The Journal of antibiotics
دوره 44 4 شماره
صفحات -
تاریخ انتشار 1991