Tyrphostin deriv. 33 | 133550-25-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: Tyrphostin deriv. 33
• 英文别名: (E)-3-(3,4-dihydroxyphenyl)-2-(4-nitrobenzoyl)prop-2-enenitrile
• CAS: 133550-25-1
• 化学式: C₁₆H₁₀N₂O₅
• 分子量: 310.266
• InChiKey: WSDDCSPJUMHQSE-KPKJPENVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  127
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  tert-butyl (Z)-2-cyano-3-hydroxy-3-(4-nitrophenyl)-2-propenoate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 Tyrphostin deriv. 33
  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