[(2S,3S)-2-amino-3-hydroxy-hexyl]-(2,4-dimethyl-benzyl)-carbamic acid benzyl ester | 1373237-44-5

• 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: [(2S,3S)-2-amino-3-hydroxy-hexyl]-(2,4-dimethyl-benzyl)-carbamic acid benzyl ester
• 英文别名: benzyl N-[(2S,3S)-2-amino-3-hydroxyhexyl]-N-[(2,4-dimethylphenyl)methyl]carbamate
• CAS: 1373237-44-5
• 化学式: C₂₃H₃₂N₂O₃
• 分子量: 384.519
• InChiKey: FQCFAROHBDJXRW-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  75.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(2S,3S)-2-amino-3-hydroxy-hexyl]-(2,4-dimethyl-benzyl)-carbamic acid benzyl ester 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 {(2S,3S)-2-[2-(3-amino-5-trifluoromethyl-phenylcarbamoyl)-acetylamino]-3-hydroxyhexyl}-(2,4-dimethyl-benzyl)-carbamic acid benzyl ester
  参考文献：
  名称：

  Discovery of an orally-bioavailable CC Chemokine Receptor 2 antagonist derived from an acyclic diaminoalcohol backbone

  摘要：

  We describe an isostere-driven approach to improve upon a previously-described series of capped dipeptide antagonists of CC Chemokine Receptor 2 (CCR2). Modification of the substitution around the isostere was combined with additional changes in a distal aromatic substituent to provide single-digit nanomolar antagonists of CCR2. These studies led to the identification of 18, a compound that was suitable for studies in murine models of CCR2 activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.007
• 作为产物：
  描述：

  2,4-二甲基苯甲醛 在 sodium cyanoborohydride 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 [(2S,3S)-2-amino-3-hydroxy-hexyl]-(2,4-dimethyl-benzyl)-carbamic acid benzyl ester
  参考文献：
  名称：

  Discovery of an orally-bioavailable CC Chemokine Receptor 2 antagonist derived from an acyclic diaminoalcohol backbone

  摘要：

  We describe an isostere-driven approach to improve upon a previously-described series of capped dipeptide antagonists of CC Chemokine Receptor 2 (CCR2). Modification of the substitution around the isostere was combined with additional changes in a distal aromatic substituent to provide single-digit nanomolar antagonists of CCR2. These studies led to the identification of 18, a compound that was suitable for studies in murine models of CCR2 activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.007

文献信息

• Malonamides and malonamide derivatives as modulators of chemokine receptor activity
  申请人：——

  公开号：US20040235835A1

  公开（公告）日：2004-11-25

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

  本申请描述了MCP-1的调节剂，其化学式为(I):1，或其药学上可接受的盐形式，用于预防哮喘、多发性硬化症、动脉粥样硬化和类风湿性关节炎。
• MALONAMIDES AND MALONAMIDE DERIVATIVES AS MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY
  申请人：Carter Percy

  公开号：US20070213379A1

  公开（公告）日：2007-09-13

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

  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，用于预防哮喘、多发性硬化症、动脉粥样硬化和类风湿性关节炎。
• US7230133B2
  申请人：——

  公开号：US7230133B2

  公开（公告）日：2007-06-12
• US7468440B2
  申请人：——

  公开号：US7468440B2

  公开（公告）日：2008-12-23