Synthesis and antibacterial activity of 7-[2-(2-aminooxazol-4-yl)-(Z)-2-alkoxyiminoacetamido]-cephalosporin antibiotics.
نویسندگان
چکیده
In a previous paper3), we reported on the synthesis and the biological activity of 3-methoxymethyl cephalosporin derivatives, one of which, cefpodoxime proxetil (Fig. 1), has been successfully developed as a prodrug for oral use. Our further elaboration for developing orally active cephalosporins has been made in the direction of chemical modification of the C-7 acyl substituent of the 3-methoxymethyl cephalosporin derivatives. 7-[2-(2-Aminooxazol-4-yl)-(Z)-2-alkoxyimino-
منابع مشابه
FK037, a new parenteral cephalosporin with a broad antibacterial spectrum: synthesis and antibacterial activity.
Sir: In recent years, a number of new parenteral cephalosporins with a broad spectrum of antibacterial activity and a high stability against various /Mactamases have been reported1}. Most of them have a 7j5-[(Z)-2-(2-aminothiazol-4-yl)-2-alkoxyiminoacetamido] side chain, such as ceftizoxime (CZX) and ceftazidime (CAZ). They show excellent activity against Gram-negative bacteria and moderate act...
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 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 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 کاملImproved synthesis of an ester-type prodrug, 1-acetoxyethyl 7-[(Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-[(Z)-1- propenyl]-3-cephem-4-carboxylate (BMY-28271).
1-Acetoxyethyl 7-[(Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3- [(Z)-1-propenyl]-3-cephem-4-carboxylate (BMY-28271) is an ester-type prodrug of cephalosporin for oral use. Methods suitable for large scale preparation were investigated. The yield was improved by esterification of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-trityloxyiminoacetamido]cep hem-4-carboxylic acid (11) followed by removal...
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 45 7 شماره
صفحات -
تاریخ انتشار 1992