Ethyl 2-[4-(1-hydroxy-4-phenylbut-3-en-2-yl)piperazin-1-yl]pyrimidine-5-carboxylate | 875138-52-6

• 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: Ethyl 2-[4-(1-hydroxy-4-phenylbut-3-en-2-yl)piperazin-1-yl]pyrimidine-5-carboxylate
• 英文别名: ethyl 2-[4-(1-hydroxy-4-phenylbut-3-en-2-yl)piperazin-1-yl]pyrimidine-5-carboxylate
• CAS: 875138-52-6
• 化学式: C₂₁H₂₆N₄O₃
• 分子量: 382.462
• InChiKey: WVGIOQHKALOMAN-UHFFFAOYSA-N

物化性质

• 沸点：
  594.1±60.0 °C(Predicted)
• 密度：
  1.225±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  78.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Ethyl 2-[4-(1-hydroxy-4-phenylbut-3-en-2-yl)piperazin-1-yl]pyrimidine-5-carboxylate 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以34%的产率得到Ethyl 2-[4-(1-methoxy-4-phenylbut-3-en-2-yl)piperazin-1-yl]pyrimidine-5-carboxylate
  参考文献：
  名称：

  Identification of a series of substituted 2-piperazinyl-5-pyrimidylhydroxamic acids as potent histone deacetylase inhibitors

  摘要：

  Pursuing our efforts in designing 5-pyrimidylhydroxamic acid anti-cancer agents, we have identified a new series of potent histone deacetylase (HDAC) inhibitors. These compounds exhibit enzymatic HDAC inhibiting properties with IC50 values in the nanomolar range and inhibit tumor cell proliferation at similar levels. Good solubility, moderate bioavailability, and promising in vivo activity in xenograft model made this series of compounds interesting starting points to design new potent HDAC inhibitors. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.118
• 作为产物：
  描述：

  乙醇醛二聚体 、 2-(哌嗪-1-基)嘧啶-5-羧酸乙酯 、 [(E)-2-苯基乙烯基]硼酸 以 乙醇 为溶剂， 生成 Ethyl 2-[4-(1-hydroxy-4-phenylbut-3-en-2-yl)piperazin-1-yl]pyrimidine-5-carboxylate
  参考文献：
  名称：

  Identification of a series of substituted 2-piperazinyl-5-pyrimidylhydroxamic acids as potent histone deacetylase inhibitors

  摘要：

  Pursuing our efforts in designing 5-pyrimidylhydroxamic acid anti-cancer agents, we have identified a new series of potent histone deacetylase (HDAC) inhibitors. These compounds exhibit enzymatic HDAC inhibiting properties with IC50 values in the nanomolar range and inhibit tumor cell proliferation at similar levels. Good solubility, moderate bioavailability, and promising in vivo activity in xenograft model made this series of compounds interesting starting points to design new potent HDAC inhibitors. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.118