159296-68-1

Upstream product

• 91439-44-0 diphenylmethyl 7β-tert-butoxycarbonylamino-3-[(Z)-2-(pyridin-3-yl)vinyl]-3-cephem-4-carboxylate 
• 143159-43-7 (6R,7R)-7-tert-Butoxycarbonylamino-8-oxo-3-[(triphenyl-λ⁵-phosphanylidene)-methyl]-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 
• 500-22-1 3-pyridinecarboxaldehyde 
• 128438-02-8 (Z)-2-(2-amino-thiazol-4-yl)-2-trityloxyimino-acetic acid-benzotriazol-1-yl ester 

Downstream Products

• 159296-78-3 pivaloyloxymethyl 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-trityloxyiminoacetamido]-3-[(Z)-2-(pyridin-3-yl)vinyl]-3-cephem-4-carboxylate 

Relevant academic research and scientific papers

Orally active cephalosporins: Synthesis, structure-activity relationships and oral absorption of 3-[(E) and (Z)-2-substituted vinyl]- cephalosporins

A series of 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3- [(E)- and (Z)-2-substituted vinyl]-3-cephem-4-carboxylic acids was designed and synthesized using palladium-catalyzed coupling reactions of a 3- methanesulfonyloxy-3-cephem and an E substituted vinyl stannane or Wittig reaction of a 3-triphenylphosphoniummethyl cephem and an aldehyde as a key step. These compounds were evaluated for in vitro antibacterial activity and oral absorption in rats. A number of them exhibited excellent antibacterial activity against both Gram-positive and Gram-negative bacteria including Haemophilus influenzae. Among them, FR86524 (2j), having a (Z)-2-(3- pyridyl)vinyl moiety at the C-3 position, had the most well balanced activity. Although FR86254 exhibited low oral absorption, the pivaloyloxymethyl ester (23) of FR86524 showed improved oral absorption. (C) 2000 Elsevier Science Ltd.