N'-(3-allyl-2-hydroxybenzylidene)-2-chloroacetohydrazide | 1187960-05-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N'-(3-allyl-2-hydroxybenzylidene)-2-chloroacetohydrazide
• 英文别名: 2-chloro-N-[(2-hydroxy-3-prop-2-enylphenyl)methylideneamino]acetamide
• CAS: 1187960-05-9
• 化学式: C₁₂H₁₃ClN₂O₂
• 分子量: 252.7
• InChiKey: KXCFDKHBPJPBED-UHFFFAOYSA-N

物化性质

• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  61.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N'-(3-allyl-2-hydroxybenzylidene)-2-chloroacetohydrazide 、 1-(4-氟苄基)哌嗪 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 18.0h， 以86%的产率得到N'-(3-allyl-2-hydroxybenzylidene)-2-(4-(4-fluorobenzyl)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
• 作为产物：
  描述：

  (3-Allyl-2-hydroxy-benzylidene)hydrazine 、 氯乙酰氯 在 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以39%的产率得到N'-(3-allyl-2-hydroxybenzylidene)-2-chloroacetohydrazide
  参考文献：
  名称：

  [EN] DESIGN, SYNTHESIS AND EVALUATION OF PROCASPASE ACTIVATING COMPOUNDS AS PERSONALIZED ANTI-CANCER DRUGS
  [FR] CONCEPTION, SYNTHÈSE ET ÉVALUATION DE COMPOSÉS ACTIVATEURS DE PROCASPASE EN TANT QUE MÉDICAMENTS ANTICANCÉREUX PERSONNALISÉS

  摘要：

  本发明公开了涉及诱导细胞死亡（例如癌细胞）的组合物和方法。公开了用于合成和使用这些化合物的相关方法，包括在癌症治疗中使用化合物以及在细胞中选择性诱导凋亡。公开了具有比其他化合物更低神经毒性效应的化合物。

  公开号：

  WO2010091382A1