benzyl (2S,3S)-2-(3-(3-(tert-butoxycarbonyl)amino-5-(trifluoromethyl)phenylamino)-3-oxopropanamido)-3-hydroxyhex-4-ynylcarbamate | 845797-50-4

• 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 (2S,3S)-2-(3-(3-(tert-butoxycarbonyl)amino-5-(trifluoromethyl)phenylamino)-3-oxopropanamido)-3-hydroxyhex-4-ynylcarbamate
• 英文别名: benzyl N-[(2S,3S)-3-hydroxy-2-[[3-[3-[(2-methylpropan-2-yl)oxycarbonylamino]-5-(trifluoromethyl)anilino]-3-oxopropanoyl]amino]hex-4-ynyl]carbamate
• CAS: 845797-50-4
• 化学式: C₂₉H₃₃F₃N₄O₇
• 分子量: 606.599
• InChiKey: AMPDEPDZGCAGRA-GOTSBHOMSA-N

物化性质

• 沸点：
  788.7±60.0 °C(Predicted)
• 密度：
  1.335±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  43
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  155
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  benzyl (2S,3S)-2-(3-(3-(tert-butoxycarbonyl)amino-5-(trifluoromethyl)phenylamino)-3-oxopropanamido)-3-hydroxyhex-4-ynylcarbamate 在 5%-palladium/activated carbon 、 氢气 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 生成 [3-(2-{(1S,2S)-1-[(2,4-Dimethyl-benzylamino)-methyl]-2-hydroxy-pentylcarbamoyl}-acetylamino)-5-trifluoromethyl-phenyl]-carbamic acid tert-butyl 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：

  N-叔丁氧羰基-3-[(苄氧羰基)氨基]-L-丙氨酸 在 R-alphine borane 、 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 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 168.0h， 生成 benzyl (2S,3S)-2-(3-(3-(tert-butoxycarbonyl)amino-5-(trifluoromethyl)phenylamino)-3-oxopropanamido)-3-hydroxyhex-4-ynylcarbamate
  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

• Lactams of alkylated acyclic diamine derivatives as modulators of chemokine receptor activity
  申请人：Carter H. Percy

  公开号：US20050043392A1

  公开（公告）日：2005-02-24

  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.

  本申请描述了式(I)的MCP-1调节剂或其药用盐形式，可用于预防哮喘、多发性硬化症、动脉粥样硬化和类风湿性关节炎。
• [EN] N-ALKYLATED DIAMINOPROPANE DERIVATIVES AS MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY<br/>[FR] DERIVES DE DIAMINOPROPANE N-ALKYLES EN TANT QUE MODULATEURS DE L'ACTIVITE DU RECEPTEUR DE LA CHIMIOKINE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2005021499A1

  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 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)，或其药用盐形式，可用于预防哮喘、多发性硬化症、动脉粥样硬化和类风湿关节炎。
• N-alkylated diaminopropane derivatives as modulators of chemokine receptor activity
  申请人：Carter H. Percy

  公开号：US20050065147A1

  公开（公告）日：2005-03-24

  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，可用于预防哮喘、多发性硬化症、动脉粥样硬化和类风湿性关节炎。
• N-ALKYLATED DIAMINOPROPANE DERIVATIVES AS MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY
  申请人：Carter Percy H.

  公开号：US20080113976A1

  公开（公告）日：2008-05-15

  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，可用于预防哮喘、多发性硬化症、动脉粥样硬化和类风湿性关节炎。