Tyrphostin deriv. 71 | 133550-52-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: Tyrphostin deriv. 71
• 英文别名: (E)-3-(3,4-dihydroxyphenyl)-2-(piperidine-1-carbonyl)prop-2-enenitrile
• CAS: 133550-52-4
• 化学式: C₁₅H₁₆N₂O₃
• 分子量: 272.304
• InChiKey: LNRHMUVQCQDANC-XYOKQWHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  84.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  哌啶 反应 16.0h， 生成 Tyrphostin deriv. 71
  参考文献：
  名称：

  Tyrphostins. II. Heterocyclic and .alpha.-substituted benzylidenemalononitrile tyrphostins as potent inhibitors of EGF receptor and ErbB2/neu tyrosine kinases

  摘要：

  We have previously described a novel series of low molecular weight protein tyrosine kinase inhibitors which we named tyrphostins. The characteristic active pharmacophore of these compounds was the hydroxy-cis-benzylidenemalononitrile moiety. In this article we describe three novel groups of tyrphostins: (i) one group has the phenolic moiety of the cis-benzylidenemalononitrile replaced either with other substituted benzenes or with heteroaromatic rings, (ii) another is a series of conformationally constrained derivatives of hydroxy-cis-benzylidenemalononitriles in which the malononitrile moiety is fixed relative to the aromatic ring, and (iii) two groups of compounds in which the position trans to the benzenemalononitrile has been substituted by ketones and amides. Among the novel tyrphostins examined we found inhibitors which discriminate between the highly homologous EGF receptor kinase (HER1) and ErbB2/neu kinase (HER2). These findings may lead to selective tyrosine kinase blockers for the treatment of diseases in which ErbB2/neu is involved.

  DOI：

  10.1021/jm00110a022

文献信息

• [EN] AN IMPROVED PROCESS FOR PREPARATION OF (2E)-2-CYANO-3-(3,4- DIHYDROXY-5-NITROPHENYL)N,N-DIETHYL-2-PROPENAMIDE POLYMORPHIC FORM A<br/>[FR] PROCÉDÉ AMÉLIORÉ DE PRÉPARATION DE LA FORME POLYMORPHE A DU (2E)-2-CYANO-3-(3,4-DIHYDROXY-5-NITROPHÉNYL)-N,N-DIÉTHYL-2-PROPÈNAMIDE
  申请人：NEULAND LAB LTD

  公开号：WO2009084031A2

  公开（公告）日：2009-07-09

  The present invention relates to an improved, cost effective, eco-friendly and easy t handle process to manufacture substantially pure form of (2E)-2-Cyano-3-(3,4-dihydroxy-5 nitrophenyl)-N,N-diethyl-2-propenamide or (E)- N,N-diethyl-2-cyano-3-(3,4-dihyroxy-5 nitroρhenyl)-acrylamide polymorphic form A commonly known as (E)-Entacapone represente by Formula I, using ammonium acetate as a base.
• Tyrphostins. II. Heterocyclic and .alpha.-substituted benzylidenemalononitrile tyrphostins as potent inhibitors of EGF receptor and ErbB2/neu tyrosine kinases
  作者：Aviv Gazit、Nir Osherov、Israel Posner、Pnina Yaish、Enrique Poradosu、Chaim Gilon、Alexander Levitzki

  DOI：10.1021/jm00110a022

  日期：1991.6

  We have previously described a novel series of low molecular weight protein tyrosine kinase inhibitors which we named tyrphostins. The characteristic active pharmacophore of these compounds was the hydroxy-cis-benzylidenemalononitrile moiety. In this article we describe three novel groups of tyrphostins: (i) one group has the phenolic moiety of the cis-benzylidenemalononitrile replaced either with other substituted benzenes or with heteroaromatic rings, (ii) another is a series of conformationally constrained derivatives of hydroxy-cis-benzylidenemalononitriles in which the malononitrile moiety is fixed relative to the aromatic ring, and (iii) two groups of compounds in which the position trans to the benzenemalononitrile has been substituted by ketones and amides. Among the novel tyrphostins examined we found inhibitors which discriminate between the highly homologous EGF receptor kinase (HER1) and ErbB2/neu kinase (HER2). These findings may lead to selective tyrosine kinase blockers for the treatment of diseases in which ErbB2/neu is involved.