YAKHAK HOEJI (약학회지)

The Pharmaceutical Society of Korea (대한약학회)
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Synthesis of 7-Arylidene Cephalosporanates for ${\beta}-lactamase$ Inhibitor

${\beta}-Lactamase$ 억제작용이 기대되는 7-Arylidene Cephalosporanate 유도체의 합성

  • Lee, Jong-Min (Division of Medicinal Chemistry, College of Pharmacy, Chung-ang University) ;
  • Yim, Chul-Bu (Division of Medicinal Chemistry, College of Pharmacy, Chung-ang University) ;
  • Im, Chae-Uk (Division of Medicinal Chemistry, College of Pharmacy, Chung-ang University)
  • 이종민 (중앙대학교 약학대학 의약화학 교실) ;
  • 임철부 (중앙대학교 약학대학 의약화학 교실) ;
  • 임채욱 (중앙대학교 약학대학 의약화학 교실)
  • Published : 2008.08.31
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Abstract

The synthesis of 7-arylidene cephalosporanates for ${\beta}-lactamase$ inhibitor was described. The reactions of substituted benzyl halides $[1]{\sim}[3]$ with triphenylphosphine gave triphenylphcsphonium chlorides $[4]{\sim}[6]$. These phosphonium salts were treated with n-butyllithium to give ylides, which were reated with 7-oxocephalosporanate [7] by Wittig reaction to afford the 7-exomethylene cephalosporanates $[8]{\sim}[10]$. These cephalosporanates were oxidized to cephalosporanate sulfones $[11]{\sim}[13]$ with mCPBA. The deprotection of benzhydryl cephalosporanate $[8]{\sim}[13]$ with $AlCl_3$ and $NaHCO_{3}$ gave sodium salts of 7-arylidene cephalosporanates $[14]{\sim}[19]$.

Keywords

References

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