(4S,5R)-3-benzyl-5-cyclohexyl-2-oxo-oxazolidine-4-carboxylic acid | 1319734-52-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (4S,5R)-3-benzyl-5-cyclohexyl-2-oxo-oxazolidine-4-carboxylic acid
• CAS: 1319734-52-5
• 化学式: C₁₇H₂₁NO₄
• 分子量: 303.358
• InChiKey: ISFWTKUFSZDOHA-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  66.84
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (4S,5R)-3-benzyl-5-cyclohexyl-2-oxo-oxazolidine-4-carboxylic acid 在 20 % Pd(OH)2/C 、 氢气 、 potassium hydroxide 作用下， 生成 (2S,3R)-β-cyclohexylserine
  参考文献：
  名称：

  Spirodiketopiperazine-based CCR5 antagonist: Discovery of an antiretroviral drug candidate

  摘要：

  Following the discovery that hydroxylated derivative 3 (Fig. 1) was one of the oxidative metabolites of the original lead 1, it was found that hydroxylated compound 4 possesses higher in vitro anti-HIV potency than the corresponding non-hydroxylated compound 2. Structural hybridation of 4 with the orally available analog 5 resulted in another orally-available spirodiketopiperazine CCR5 antagonist 6a that possesses more favorable pharmaceutical profile for use as a drug candidate. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.109
• 作为产物：
  描述：

  3-cyclohexyl-2-propen-1-ol 在 叔丁基过氧化氢 、 Jones reagent 、 D-(-)-酒石酸二乙酯 、 titanium(IV) isopropoxide 、 sodium hydride 、 potassium hydroxide 作用下， 以 四氢呋喃 、 正辛烷 、 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 、 丙酮 为溶剂， 反应 7.5h， 生成 (4S,5R)-3-benzyl-5-cyclohexyl-2-oxo-oxazolidine-4-carboxylic acid
  参考文献：
  名称：

  Discovery of 4-[4-({(3R)-1-butyl-3-[(R)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undec-9-yl}methyl)phenoxy]benzoic acid hydrochloride: A highly potent orally available CCR5 selective antagonist

  摘要：

  Based on the original spirodiketopiperazine design framework, further optimization of an orally available CCR5 antagonist was undertaken. Structural hybridization of the hydroxylated analog 4 derived from one of the oxidative metabolites and the new orally available non-hydroxylated benzoic acid analog 5 resulted in another potent orally available CCR5 antagonist 6a as a clinical candidate. Full details of a structure-activity relationship (SAR) study and ADME properties are presented. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.022