tert-butyl (Z)-2-cyano-3-hydroxy-3-(4-nitrophenyl)-2-propenoate | 133550-24-0

• 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: tert-butyl (Z)-2-cyano-3-hydroxy-3-(4-nitrophenyl)-2-propenoate
• 英文别名: tert-butyl (Z)-2-cyano-3-hydroxy-3-(4-nitrophenyl)prop-2-enoate
• CAS: 133550-24-0
• 化学式: C₁₄H₁₄N₂O₅
• 分子量: 290.276
• InChiKey: HFYRFNMWINVICV-QXMHVHEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  氰乙酸叔丁酯 、 4-硝基苯甲酰氯 在 sodium hydride 作用下， 生成 tert-butyl (Z)-2-cyano-3-hydroxy-3-(4-nitrophenyl)-2-propenoate
  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

• MST1 KINASE INHIBITORS AND METHODS OF THEIR USE
  申请人：Augeri David John

  公开号：US20120225857A1

  公开（公告）日：2012-09-06

  Compounds for the inhibition of mammalian Ste20-like kinase 1 (MST1) are disclosed, along with compositions comprising them and methods of their use in the treatment, management or prevention of an inflammatory or autoimmune diseases or disorders.

  揭示了用于抑制哺乳动物Ste20样激酶1（MST1）的化合物，以及包含它们的组合物和在治疗、管理或预防炎症性或自身免疫疾病或紊乱中使用它们的方法。
• US8440652B2
  申请人：——

  公开号：US8440652B2

  公开（公告）日：2013-05-14