N-[2-(S)-(3,4-dichlorophenyl)-3-carboxypropyl]-N-methyl-3-cyano-2-methoxy-1-naphthamide | 367249-64-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-[2-(S)-(3,4-dichlorophenyl)-3-carboxypropyl]-N-methyl-3-cyano-2-methoxy-1-naphthamide
• 英文别名: N-[2-(R)-(3,4-dichlorophenyl)-3-carboxypropyl]-N-methyl-3-cyano-2-methoxy-1-naphthamide；(3S)-4-[(3-cyano-2-methoxynaphthalene-1-carbonyl)-methylamino]-3-(3,4-dichlorophenyl)butanoic acid
• CAS: 367249-64-7
• 化学式: C₂₄H₂₀Cl₂N₂O₄
• 分子量: 471.34
• InChiKey: UNSIYMNPMQCIHK-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  90.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[2-(S)-(3,4-dichlorophenyl)-3-carboxypropyl]-N-methyl-3-cyano-2-methoxy-1-naphthamide 在 N,N-二异丙基乙胺 、 fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate 、 ammonium hydroxybenzotriazole 作用下， 以 二氯甲烷 为溶剂， 反应 0.83h， 以80%的产率得到N-[2-(S)-(3,4-dichlorophenyl)-3-aminocarbonylpropyl]-N-methyl-3-cyano-2-methoxy-1-naphthamide
  参考文献：
  名称：

  Structural Analysis and Optimization of NK₁ Receptor Antagonists through Modulation of Atropisomer Interconversion Properties

  摘要：

  We have previously described a series of antagonists that showed high potency and selectivity for the NK1 receptor. However, these compounds also had the undesirable property of existing as a mixture of interconverting rotational isomers. Here we show that alteration of the 2-naphthyl substituent can modulate the rate of isomer exchange. Comparisons of the NK1 receptor affinity for the various conformational. forms has facilitated the development of a detailed NK1 pharmacophore model.

  DOI：

  10.1021/jm030197g
• 作为产物：
  描述：

  N-[2-(S)-(3,4-dichlorophenyl)-4-hydroxybutyl]-N-methylamine 在 重铬酸吡啶 、 碳酸氢钠 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 N-[2-(S)-(3,4-dichlorophenyl)-3-carboxypropyl]-N-methyl-3-cyano-2-methoxy-1-naphthamide
  参考文献：
  名称：

  Structural Analysis and Optimization of NK₁ Receptor Antagonists through Modulation of Atropisomer Interconversion Properties

  摘要：

  We have previously described a series of antagonists that showed high potency and selectivity for the NK1 receptor. However, these compounds also had the undesirable property of existing as a mixture of interconverting rotational isomers. Here we show that alteration of the 2-naphthyl substituent can modulate the rate of isomer exchange. Comparisons of the NK1 receptor affinity for the various conformational. forms has facilitated the development of a detailed NK1 pharmacophore model.

  DOI：

  10.1021/jm030197g

文献信息

• Novel n-( 2-phenyl-3-aminopropyl)naphtamides
  申请人：——

  公开号：US20040014809A1

  公开（公告）日：2004-01-22

  A compound of the formula 1 wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , X 1 and X 2 are as defined in the specification useful for the treatment of diseases in which action of the neurokinin 1 receptor is implicated, methods of using such compounds and pharmaceutical compositions comprising such compounds.

  一种化合物的公式如下，其中R1、R2、R3、R4、R5、R6、X1和X2如规范中定义，用于治疗神经激肽1受体作用所涉及的疾病，使用这种化合物的方法以及包含这种化合物的药物组合物。
• Naphthamide neurokinin antagonists for use as medicaments
  申请人：——

  公开号：US20030158180A1

  公开（公告）日：2003-08-21

  A compound having the general formula (Ia) and methods of using such compounds for the treatment of diseases and pharmaceutical composition comprising such compounds.

  一种具有一般式(Ia)的化合物以及使用这种化合物治疗疾病的方法和包含这种化合物的制药组合物。
• NAPHTHAMIDE NEUROKININ ANTAGONISTS FOR USE AS MEDICAMENTS
  申请人：AstraZeneca AB

  公开号：EP1278719A1

  公开（公告）日：2003-01-29
• NOVEL N-(2-PHENYL-3-AMINOPROPYL)NAPHTAMIDES
  申请人：AstraZeneca AB

  公开号：EP1307425B1

  公开（公告）日：2005-04-20
• US6903092B2
  申请人：——

  公开号：US6903092B2

  公开（公告）日：2005-06-07