Studies on beta-lactam antibiotics. II. Synthesis and antibacterial activity of cephalosporins with substituted 1,3-dithietane directly attached to the C-3 position.
نویسندگان
چکیده
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.
منابع مشابه
Studies on monocyclic beta-lactam antibiotics. II. Synthesis and antibacterial activity of 3-acylamino-2-azetidinone-1-oxysulfonic acids.
The synthesis and in vitro antibacterial and beta-lactamase inhibitory activity of the 2-azetidinone-1-oxysulfonic acids having a substituent at C-4 position of the beta-lactam ring are described. The influence of C-4 substituents on the antibacterial activity was examined for the compounds having alpha-ureidoacetyl or alpha-oxyiminoacetyl group as acyl side chain at C-3 position. The antibacte...
متن کاملStudies on beta-lactam antibiotics. XIX. Structure-activity relationships of cephalosporins having a thiadiazolylthiomethyl group at the C-3 side chain.
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 کاملSTUDIES ON CEPHALOSPORIN ANTIBIOTICS III. SYNTHESIS, ANTIBACTERIAL ACTIVITY AND ORAL ABSORPTION OF NEW 3-(SUBSTITUTED-ALKYLTHIO)-7j8-[(Z)-2-(2-AMINOTHIAZOL-4-YL)- 2-(CARBOXYMETHOXYIMINO)ACETAMIDO] CEPHALOSPORINS
The synthesis, antibacterial activity and oral absorption in rats of new 7/?-[(Z)-2-(2-aminothiazol4-yl)-2-(carboxymethoxyimino)acetamido]cephalosporins (1) having various substituted-alkylthio groups at the C-3 position of the cephemnucleus are described. Of these, the cephalosporins with a cyanomethylthio group (Id) and fluoroethylthio group (lp) at the C-3 position showed a potent in vitro a...
متن کاملStudies on orally active cephalosporins. II. Synthesis and structure-activity relations of new [(E) or (Z) 3-substituted carbamoyloxy]-1-propenyl cephalosporins.
In an effort to find a new oral cephalosporin with well-balanced antibacterial spectrum, good oral absorbability and long plasma half-life, a series of oxyimino aminothiazolyl 3-[(E)- or (Z)-N-substituted carbamoyloxy]propenyl cephems was synthesized and evaluated for antibacterial activity and oral absorbability. The substituents of the carbamoyloxy group affected their in vitro activity and b...
متن کاملSTUDIES ON CEPHALOSPORIN ANTIBIOTICS IV. SYNTHESIS, ANTIBACTERIAL ACTIVITY AND ORAL ABSORPTION OF NEW 3-(2-SUBSTITUTED-VINYLTHIO)-7j5- [(Z)-2-(2-AMINOTHIAZOL-4-YL)-2-
A series of new 7j5-[(Z)-2-(2-aminothiazol-4-yl)-2-(carboxymethoxyimino)acetamido]cephalosporins (1) having various substituted-vinylthio groups at the C-3 position of the cephem nucleus was synthesized and evaluated for antibacterial activity and oral absorption in rats in comparison with cefixime. Of these, the cephalosporins (la and lc) with a lower alkoxycarbonylvinylthio group (Z-form) at ...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- The Journal of antibiotics
دوره 44 4 شماره
صفحات -
تاریخ انتشار 1991