189099-43-2

Upstream product

• 35011-25-7 ethyl (2Z)-2-(hydroxyimino)-3-oxopentanoate 
• 189099-14-7 ethyl (Z)-2-(5-methyl-2-tritylaminothiazol-4-yl)-2-(trityloxyimino)acetate 
• 189099-13-6 ethyl (Z)-2-hydroxyamino-2-(5-methyl-2-tritylaminothiazol-4-yl)acetate 
• 189099-12-5 ethyl (Z)-2-(2-amino-5-methylthiazol-4-yl)-2-(hydroxyimino)acetate 
• 189099-11-4 ethyl (Z)-4-chloro-2-hydroxyimino-3-oxopentanoate 
• 74704-03-3 diphenylmethyl 7β-amino-3-methanesulfonyloxy-3-cephem-4-carboxylate 
• 189099-15-8 (Z)-2-(5-methyl-2-tritylaminothiazol-4-yl)-2-(trityloxyimino)acetic acid 
• 189099-17-0 diphenylmethyl 7β-amino-3-[(1-tritylpyrazol-4-yl)methylthio]-3-cephem-4-carboxylate 

Relevant academic research and scientific papers

Orally active cephalosporins. Part 4: Synthesis, structure-activity relationships and oral absorption of novel 3-(4-pyrazolylmethylthio)cephalosporins with various C-7 side chains

A series of 3-(4-pyrazolylmethylthio)cephalosporins with various C-7 side chains was designed, synthesized and evaluated for antibacterial activity and oral absorption in rats. Antibacterial activity against Haemophilus influenzae was markedly increased by the C-7 oxime moiety. Deamination at the 2 position of, or introduction of a substituent such as halogen or methyl to, the 5 position of the (Z)-2-(2-aminothiazol-4-yl)-2-(hydroxyimino) moiety improved oral absorption. Among these compounds, FR192752 (40a) having a (Z)-2-(2-amino-5-chlorothiazol-4-yl)-2-hydroxyiminoacetamido moiety, showed potent antibacterial activity against both Gram-positive and Gram-negative bacteria including H. influenzae and penicillin G-resistant Streptococcus pneumoniae (PRSP). Further, it showed higher oral absorption than CFDN and FK041.