N'-(3-allyl-2-hydroxybenzylidene)-2-(4-(3-nitrobenzyl)piperazin-1-yl)acetohydrazide | 1187960-36-6

• 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: N'-(3-allyl-2-hydroxybenzylidene)-2-(4-(3-nitrobenzyl)piperazin-1-yl)acetohydrazide
• 英文别名: N-[(2-hydroxy-3-prop-2-enylphenyl)methylideneamino]-2-[4-[(3-nitrophenyl)methyl]piperazin-1-yl]acetamide
• CAS: 1187960-36-6
• 化学式: C₂₃H₂₇N₅O₄
• 分子量: 437.498
• InChiKey: QMBYIVZXBKVZSR-UHFFFAOYSA-N

物化性质

• 熔点：
  84-86 °C
• 密度：
  1.26±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-烯丙基-2-羟基苯甲醛 、 2-(4-(3-nitrobenzyl)piperazin-1-yl)acetohydrazide 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 以74%的产率得到N'-(3-allyl-2-hydroxybenzylidene)-2-(4-(3-nitrobenzyl)piperazin-1-yl)acetohydrazide
  参考文献：
  名称：

  Procaspase-3 Activation as an Anti-Cancer Strategy: Structure−Activity Relationship of Procaspase-Activating Compound 1 (PAC-1) and Its Cellular Co-Localization with Caspase-3

  摘要：

  A goal of personalized medicine as applied to oncology is to identify compounds that exploit a defined molecular defect in a cancerous cell. A compound called procaspase-activating compound I (PAC-1) was reported that enhances the activity of procaspase-3 in vitro and induces apoptotic death in cancer cells in culture and in mouse xenograft models. Experimental evidence indicates that PAC-1 activates procaspase-3 in vitro through chelation of inhibitory zinc ions. Described herein is the synthesis and biological activity of a family of PAC-1 derivatives where key functional groups have been systematically altered. Analysis of these compounds reveals a strong correlation between the in vitro procaspase-3 activating effect and their ability to induce death in cancer cells in culture. Importantly, we also show that a fluorescently labeled version of PAC-1 co-localizes with sites of caspase-3 activity in cancer cells. The data presented herein further bolster the hypothesis that PAC-1 induces apoptosis in cancer cells through the direct activation of procaspase-3, has implications for the design and discovery of next-generation procaspase-3 activating compounds, and sheds light on the anti-apoptotic role of cellular zinc.

  DOI：

  10.1021/jm900722z