(3S,4R)-4-[4-(Benzyloxy)phenyl]-3-(4-fluorophenyl)-1-\ [(S)-1-(4-methoxyphenyl)ethyl]azetidin-2-one | 926657-20-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (3S,4R)-4-[4-(Benzyloxy)phenyl]-3-(4-fluorophenyl)-1-\ [(S)-1-(4-methoxyphenyl)ethyl]azetidin-2-one
• 英文别名: (3S,4R)-3-(4-fluorophenyl)-1-[(1S)-1-(4-methoxyphenyl)ethyl]-4-(4-phenylmethoxyphenyl)azetidin-2-one
• CAS: 926657-20-7
• 化学式: C₃₁H₂₈FNO₃
• 分子量: 481.567
• InChiKey: DBYNPSDKHGNXFA-NRAUDTLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.84
• 重原子数：
  36.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3S,4R)-4-[4-(Benzyloxy)phenyl]-3-(4-fluorophenyl)-1-\ [(S)-1-(4-methoxyphenyl)ethyl]azetidin-2-one 在 ammonium cerium(IV) nitrate 作用下， 以55%的产率得到(3S,4R)-3-(4-Fluorophenyl)-4-[4-(phenylmethoxy)phenyl]-2-azetidinone
  参考文献：
  名称：

  Ezetimibe analogs with a reorganized azetidinone ring: Design, synthesis, and evaluation of cholesterol absorption inhibitions

  摘要：

  The underlying principle of drug design in this paper is that the maximum retention of the functional groups that exist in the marketed drug would provide a higher probability for comparable safety while the conformational changes in the newly created analogs should not constitute a significant structural variation to adversely affect biological activity. Four individual isomers of backbone re-organized ezetimibe analogs were designed and synthesized. Their effects on the cholesterol levels in rat serum were evaluated by a high-cholesterol and high-fat diet feeding experiment. All the new analogs showed significant effect in lowering the levels of total cholesterol in serum. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.078
• 作为产物：
  描述：

  4-苄氧基苯甲醛 在 三乙胺 作用下， 以 甲苯 为溶剂， 生成 (3S,4R)-4-[4-(Benzyloxy)phenyl]-3-(4-fluorophenyl)-1-\ [(S)-1-(4-methoxyphenyl)ethyl]azetidin-2-one
  参考文献：
  名称：

  Ezetimibe analogs with a reorganized azetidinone ring: Design, synthesis, and evaluation of cholesterol absorption inhibitions

  摘要：

  The underlying principle of drug design in this paper is that the maximum retention of the functional groups that exist in the marketed drug would provide a higher probability for comparable safety while the conformational changes in the newly created analogs should not constitute a significant structural variation to adversely affect biological activity. Four individual isomers of backbone re-organized ezetimibe analogs were designed and synthesized. Their effects on the cholesterol levels in rat serum were evaluated by a high-cholesterol and high-fat diet feeding experiment. All the new analogs showed significant effect in lowering the levels of total cholesterol in serum. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.078