methyl (E)-3-(3-nitro-4-((3-(pyrrolidin-1-yl)propyl)amino)phenyl)acrylate | 1145979-43-6

• 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: methyl (E)-3-(3-nitro-4-((3-(pyrrolidin-1-yl)propyl)amino)phenyl)acrylate
• CAS: 1145979-43-6
• 化学式: C₁₇H₂₃N₃O₄
• 分子量: 333.387
• InChiKey: TZVXTKKJWWTHHH-SOFGYWHQSA-N

物化性质

• 沸点：
  515.4±50.0 °C(predicted)
• 密度：
  1.232±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.68
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  84.71
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  苯丙醛 、 methyl (E)-3-(3-nitro-4-((3-(pyrrolidin-1-yl)propyl)amino)phenyl)acrylate 在 tin(II) chloride dihydrate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 生成 methyl (E)-3-(2-phenethyl-1-(3-(pyrrolidin-1-yl)propyl)-1H-benzo[d]imidazol-5-yl)acrylate
  参考文献：
  名称：

  N-Hydroxy-1,2-disubstituted-1H-benzimidazol-5-yl acrylamides as novel histone deacetylase inhibitors: Design, synthesis, SAR studies, and in vivo antitumor activity

  摘要：

  A series of N-hydroxy-1,2-disubstituted-1H-benzimidazol-5-yl acrylamides were designed and synthesized as novel HDAC inhibitors. General SAR has been established for the substituents at positions 1 and 2, as well as the importance of the ethylene group and its attachment to position 5. Optimized compounds are much more potent than SAHA in both enzymatic and cellular assays. A representative compound, 23 (SB639), has demonstrated antitumor activity in a colon cancer xenograft model. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.01.041
• 作为产物：
  描述：

  甲醇 、 (E)-3-(3-nitro-4-((3-(pyrrolidin-1-yl)propyl)amino)phenyl)acrylic acid 在 硫酸 作用下， 生成 methyl (E)-3-(3-nitro-4-((3-(pyrrolidin-1-yl)propyl)amino)phenyl)acrylate
  参考文献：
  名称：

  N-Hydroxy-1,2-disubstituted-1H-benzimidazol-5-yl acrylamides as novel histone deacetylase inhibitors: Design, synthesis, SAR studies, and in vivo antitumor activity

  摘要：

  A series of N-hydroxy-1,2-disubstituted-1H-benzimidazol-5-yl acrylamides were designed and synthesized as novel HDAC inhibitors. General SAR has been established for the substituents at positions 1 and 2, as well as the importance of the ethylene group and its attachment to position 5. Optimized compounds are much more potent than SAHA in both enzymatic and cellular assays. A representative compound, 23 (SB639), has demonstrated antitumor activity in a colon cancer xenograft model. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.01.041