159492-75-8Relevant academic research and scientific papers
Orally active cephalosporins: Synthesis, structure-activity relationships and oral absorption of 3-[(E) and (Z)-2-substituted vinyl]- cephalosporins
Yamamoto, Hirofumi,Terasawa, Takeshi,Ohki, Ayako,Shirai, Fumiyuki,Kawabata, Kohji,Sakane, Kazuo,Matsumoto, Satoru,Matsumoto, Yoshimi,Tawara, Shuichi
, p. 43 - 54 (2007/10/03)
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.
