(2R,3R)-2-(t-butoxycarbonylamino)-3-cycloheptyl-3-hydroxy-propanoic acid | 578717-45-0

• 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: (2R,3R)-2-(t-butoxycarbonylamino)-3-cycloheptyl-3-hydroxy-propanoic acid
• 英文别名: (2R,3R)-3-cycloheptyl-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 578717-45-0
• 化学式: C₁₅H₂₇NO₅
• 分子量: 301.383
• InChiKey: ICNXTYVFVCRXFL-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2-(t-butoxycarbonylamino)-3-cycloheptyl-3-hydroxy-propanoic acid 在 sodium tris(acetoxy)borohydride 、 20 % Pd(OH)2/C 、 氢气 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 50.0~80.0 ℃ 、101.33 kPa 条件下， 反应 5.0h， 生成 4-[4-(((3R)-1-butyl-3-[(R)-cycloheptyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undec-9-yl)methyl)phenoxy]benzoic acid hydrochloride
  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
• 作为产物：
  描述：

  在 盐酸 、 lithium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 4.0h， 生成 (2R,3R)-2-(t-butoxycarbonylamino)-3-cycloheptyl-3-hydroxy-propanoic 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