benzyl (S)-1-[(1S,2R,4R)-4-(isopropyl(methyl)amino)-2-propylcyclohexyl]-2-oxopyrrolidin-3-ylcarbamate | 848001-50-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl (S)-1-[(1S,2R,4R)-4-(isopropyl(methyl)amino)-2-propylcyclohexyl]-2-oxopyrrolidin-3-ylcarbamate
• 英文别名: benzyl N-[(3S)-1-[(1S,2R,4R)-4-[methyl(propan-2-yl)amino]-2-propylcyclohexyl]-2-oxopyrrolidin-3-yl]carbamate
• CAS: 848001-50-3
• 化学式: C₂₅H₃₉N₃O₃
• 分子量: 429.603
• InChiKey: WRYOUPWRAWAPDX-LUKWVAJMSA-N

物化性质

• 沸点：
  588.0±50.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  61.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl (S)-1-[(1S,2R,4R)-4-(isopropyl(methyl)amino)-2-propylcyclohexyl]-2-oxopyrrolidin-3-ylcarbamate 在 氢溴酸 、 溶剂黄146 、 三乙胺 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 14.42h， 生成 (3S)-3-[(6-chloroquinazolin-4-yl)amino]-1-[(1S,2R,4R)-4-[methyl(propan-2-yl)amino]-2-propylcyclohexyl]pyrrolidin-2-one
  参考文献：
  名称：

  Discovery of a Potent and Orally Bioavailable Dual Antagonist of CC Chemokine Receptors 2 and 5

  摘要：

  We describe the hybridization of our previously reported acyclic and cyclic CC chemokine receptor 2 (CCR2) antagonists to lead to a new series of dual antagonists of CCR2 and CCRS. Installation of a gamma-lactam as the spacer group and a quinazoline as a benzamide mimetic improved oral bioavailability markedly. These efforts led to the identification of 13d, a potent and orally bioavailable dual antagonist suitable for use in both murine and monkey models of inflammation.

  DOI：

  10.1021/ml500505q
• 作为产物：
  描述：

  {(3S)-1-[(1S,2R,4R)-4-tert-butoxycarbonylamino-2-propylcyclohexyl]-2-oxopyrrolidin-3-yl}carbamic acid benzyl ester 在 sodium cyanoborohydride 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 24.17h， 生成 benzyl (S)-1-[(1S,2R,4R)-4-(isopropyl(methyl)amino)-2-propylcyclohexyl]-2-oxopyrrolidin-3-ylcarbamate
  参考文献：
  名称：

  Discovery of a Potent and Orally Bioavailable Dual Antagonist of CC Chemokine Receptors 2 and 5

  摘要：

  We describe the hybridization of our previously reported acyclic and cyclic CC chemokine receptor 2 (CCR2) antagonists to lead to a new series of dual antagonists of CCR2 and CCRS. Installation of a gamma-lactam as the spacer group and a quinazoline as a benzamide mimetic improved oral bioavailability markedly. These efforts led to the identification of 13d, a potent and orally bioavailable dual antagonist suitable for use in both murine and monkey models of inflammation.

  DOI：

  10.1021/ml500505q

文献信息

• Cyclic derivatives as modulators of chemokine receptor activity
  申请人：Carter H. Percy

  公开号：US20050054627A1

  公开（公告）日：2005-03-10

  The present application describes modulators of MCP-1 of formula (I): or pharmaceutically acceptable salt forms thereof, useful for the treatment of rheumatoid arthritis, multiple sclerosis, atherosclerosis and asthma.

  当前申请描述了MCP-1的调节剂，其化学公式为(I):或其药用可接受的盐形式，用于治疗类风湿性关节炎、多发性硬化症、动脉粥样硬化和哮喘。
• CYCLIC DERIVATIVES AS MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY
  申请人：Carter Percy H.

  公开号：US20090124668A1

  公开（公告）日：2009-05-14

  The present application describes modulators of MCP-1 of formula (I): or pharmaceutically acceptable salt forms thereof, useful for the treatment of rheumatoid arthritis, multiple sclerosis, atherosclerosis and asthma.

  本申请描述了 MCP-1 的调节剂，其化学式为 (I) 或其药学上可接受的盐形式，适用于治疗类风湿性关节炎、多发性硬化症、动脉粥样硬化和哮喘。