2-cyano-N-[3-[4-[3-[(2-cyanoacetyl)amino]propyl]piperazin-1-yl]propyl]acetamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 2-cyano-N-[3-[4-[3-[(2-cyanoacetyl)amino]propyl]piperazin-1-yl]propyl]acetamide
• 化学式: C₁₆H₂₆N₆O₂
• 分子量: 334.421
• InChiKey: CBDXIDNSHSQFRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-cyano-N-[3-[4-[3-[(2-cyanoacetyl)amino]propyl]piperazin-1-yl]propyl]acetamide 、 3,4-二羟基苯甲醛 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以89%的产率得到(E)-2-cyano-N-[3-[4-[3-[[(E)-2-cyano-3-(3,4-dihydroxyphenyl)prop-2-enoyl]amino]propyl]piperazin-1-yl]propyl]-3-(3,4-dihydroxyphenyl)prop-2-enamide
  参考文献：
  名称：

  Tyrphostins. 6. Dimeric Benzylidenemalononitrile Tyrphostins:  Potent Inhibitors of EGF Receptor Tyrosine Kinase in Vitro

  摘要：

  Benzylidenemalononitrile (BMN) tyrphostins were previously found to be potent inhibitors of EGF receptor (EGFR) tyrosine kinase activity. Since these compounds were found to compete for the substrate and sometimes with the ATP site and since EGFR acts as a dimer, we prepared a series of dimeric tyrphostins. These dimeric tyrphostins were built from two BMN units linked by various spacers and designed to fit the dimeric cross-autophosphorylation signal transduction intermediate of the EGFR tyrosine kinases. Structure-activity relationship of these potent dimeric EGF receptor tyrosine kinase inhibitors is reported.

  DOI：

  10.1021/jm960225d
• 作为产物：
  描述：

  1,4-双(3-氨基丙基)哌嗪 、 氰乙酸甲酯 反应 1.0h， 以64%的产率得到2-cyano-N-[3-[4-[3-[(2-cyanoacetyl)amino]propyl]piperazin-1-yl]propyl]acetamide
  参考文献：
  名称：

  Tyrphostins. 6. Dimeric Benzylidenemalononitrile Tyrphostins:  Potent Inhibitors of EGF Receptor Tyrosine Kinase in Vitro

  摘要：

  Benzylidenemalononitrile (BMN) tyrphostins were previously found to be potent inhibitors of EGF receptor (EGFR) tyrosine kinase activity. Since these compounds were found to compete for the substrate and sometimes with the ATP site and since EGFR acts as a dimer, we prepared a series of dimeric tyrphostins. These dimeric tyrphostins were built from two BMN units linked by various spacers and designed to fit the dimeric cross-autophosphorylation signal transduction intermediate of the EGFR tyrosine kinases. Structure-activity relationship of these potent dimeric EGF receptor tyrosine kinase inhibitors is reported.

  DOI：

  10.1021/jm960225d

文献信息

• New chromene scaffolds for adenosine A2A receptors: Synthesis, pharmacology and structure–activity relationships
  作者：Filipe Areias、Marta Costa、Marián Castro、José Brea、Elisabet Gregori-Puigjané、M. Fernanda Proença、Jordi Mestres、María I. Loza

  DOI：10.1016/j.ejmech.2012.05.009

  日期：2012.8

  In silico screening of a c ollection of 1584 academic compounds identified a small molecule hit for the human adenosine A(2A) receptor (pK(i) = 6.2) containing a novel chromene scaffold (3a). To explore the structure activity relationships of this new chemical series for adenosine receptors, a focused library of 43 2H-chromene-3-carboxamide derivatives was synthesized and tested in radioligand binding assays at human adenosine A(1), A(2A), A(2B) and A(3) receptors. The series was found to be enriched with bioactive compounds for adenosine receptors, with 14 molecules showing submicromolar affinity (pK(i) >= 6.0) for at least one adenosine receptor subtype. These results provide evidence that the chromene scaffold, a core structure present in natural products from a wide variety of plants, vegetables, and fruits, constitutes a valuable source for novel therapeutic agents. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Tyrphostins. 6. Dimeric Benzylidenemalononitrile Tyrphostins:  Potent Inhibitors of EGF Receptor Tyrosine Kinase <i>in Vitro</i>
  作者：Aviv Gazit、Nir Osherov、Chaim Gilon、Alexander Levitzki

  DOI：10.1021/jm960225d

  日期：1996.1.1

  Benzylidenemalononitrile (BMN) tyrphostins were previously found to be potent inhibitors of EGF receptor (EGFR) tyrosine kinase activity. Since these compounds were found to compete for the substrate and sometimes with the ATP site and since EGFR acts as a dimer, we prepared a series of dimeric tyrphostins. These dimeric tyrphostins were built from two BMN units linked by various spacers and designed to fit the dimeric cross-autophosphorylation signal transduction intermediate of the EGFR tyrosine kinases. Structure-activity relationship of these potent dimeric EGF receptor tyrosine kinase inhibitors is reported.