3-(4-fluorophenyl)-4R-(2-hydroxyphenyl)-5S-(1R-hydroxy-3-phenylpropyl)oxazolidin-2-one | 1011265-15-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-(4-fluorophenyl)-4R-(2-hydroxyphenyl)-5S-(1R-hydroxy-3-phenylpropyl)oxazolidin-2-one
• 英文别名: (4R,5S)-3-(4-fluorophenyl)-4-(2-hydroxyphenyl)-5-[(1R)-1-hydroxy-3-phenylpropyl]-1,3-oxazolidin-2-one
• CAS: 1011265-15-8
• 化学式: C₂₄H₂₂FNO₄
• 分子量: 407.441
• InChiKey: GWXQKSOMHYPUFN-DNVJHFABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  70
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 palladium on activated charcoal 环己烯 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 5.0h， 生成 3-(4-fluorophenyl)-4R-(2-hydroxyphenyl)-5S-(1R-hydroxy-3-phenylpropyl)oxazolidin-2-one
  参考文献：
  名称：

  Substituted oxazolidinones as novel NPC1L1 ligands for the inhibition of cholesterol absorption

  摘要：

  Cholesterol absorption inhibition (CAI) represents an important treatment option for hypercholesterolemia. Herein, we report the design and evaluation of a series of substituted oxazolidinones as ligands for the Niemann Pick C1 Like 1 (NPC1L1) protein, a key mediator of cholesterol transport. Novel analogs were initially evaluated in a brush border membrane NPC1L1 binding assay; subsequently, promising compounds were evaluated in vivo for acute inhibition of cholesterol absorption. These studies identified analogs with low micromolar NPC1L1 binding affinity and acute in vivo efficacy of >50% absorption inhibition at 3 mg/kg. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.083