2-(4-benzyl-1-piperazinyl)-N'-[(E)-(2-chlorophenyl)methylidene]acetohydrazide

• 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-(4-benzyl-1-piperazinyl)-N'-[(E)-(2-chlorophenyl)methylidene]acetohydrazide
• 英文别名: 2-(4-benzylpiperazin-1-yl)-N-[(E)-(2-chlorophenyl)methylideneamino]acetamide
• 化学式: C₂₀H₂₃ClN₄O
• 分子量: 370.882
• InChiKey: VOJWBWSQEOGCSO-HYARGMPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氯苯甲醛 、 4-(苯甲基)-1-哌嗪乙酸 在 盐酸 作用下， 以 乙醇 为溶剂， 生成 2-(4-Benzylpiperazin-1-YL)-N'-[(Z)-(2-chlorophenyl)methylidene]acetohydrazide 、 2-(4-benzyl-1-piperazinyl)-N'-[(E)-(2-chlorophenyl)methylidene]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

文献信息

• Compounds and methods for the treatment of cancer
  申请人：The Board of Trustees of the University of Illinois

  公开号：US10166229B2

  公开（公告）日：2019-01-01

  Compositions and methods are disclosed in embodiments relating to induction of cell death such as in cancer cells. Compounds and related methods for synthesis and use thereof, including the use of compounds in therapy for the treatment of cancer and selective induction of apoptosis in cells are disclosed. Compounds are disclosed in connection with modification of procaspases such as procaspase-3. In embodiments, compositions are capable of activation of procaspase-3.

  在有关诱导细胞死亡（如癌细胞）的实施方案中，公开了化合物和方法。公开了化合物及其合成和使用的相关方法，包括在治疗癌症和选择性诱导细胞凋亡的疗法中使用化合物。所公开的化合物涉及对原蛋白酶（如原蛋白酶-3）的修饰。在实施方案中，组合物能够激活procaspase-3。
• Compositions and Methods Including Cell Death Inducers and Procaspase Activation
  申请人：HERGENROTHER Paul J.

  公开号：US20110257398A1

  公开（公告）日：2011-10-20

  Compositions and methods are disclosed in embodiments relating to induction of cell death such as in cancer cells. Compounds and related methods for synthesis and use thereof, including the use of compounds in therapy for the treatment of cancer and selective induction of apoptosis in cells are disclosed. Compounds are disclosed in connection with modification of procaspases such as procaspase-3. In embodiments, compositions are capable of activation of procaspase-3.
• COMPOUNDS AND METHODS FOR THE TREATMENT OF CANCER
  申请人：The Board of Trustees of the University of Illinois

  公开号：US20170105989A1

  公开（公告）日：2017-04-20

  Compositions and methods are disclosed in embodiments relating to induction of cell death such as in cancer cells. Compounds and related methods for synthesis and use thereof, including the use of compounds in therapy for the treatment of cancer and selective induction of apoptosis in cells are disclosed. Compounds are disclosed in connection with modification of procaspases such as procaspase-3. In embodiments, compositions are capable of activation of procaspase-3.
• US9522901B2
  申请人：——

  公开号：US9522901B2

  公开（公告）日：2016-12-20
• [EN] COMPOSITIONS AND METHODS INCLUDING CELL DEATH INDUCERS AND PROCASPASE ACTIVATION<br/>[FR] COMPOSITIONS ET PROCÉDÉS COMPORTANT DES INDUCTEURS DE MORT CELLULAIRE ET D'ACTIVATION DE PROCASPASE
  申请人：UNIV ILLINOIS

  公开号：WO2008134474A2

  公开（公告）日：2008-11-06

  [EN] Compositions and methods are disclosed in embodiments relating to induction of cell death such as in cancer cells. Compounds and related methods for synthesis and use thereof, including the use of compounds in therapy for the treatment of cancer and selective induction of apoptosis in cells are disclosed. Compounds are disclosed in connection with modification of procaspases such as procaspase-3. In embodiments, compositions are capable of activation of procaspase-3.
  [FR] Selon certains modes de réalisation, la présente invention concerne des compositions et des procédés associés à l'induction de mort cellulaire telle que dans des cellules cancéreuses. L'invention concerne également des composés et des procédés associés pour la synthèse et leur utilisation, comprenant l'utilisation de composés dans la thérapie pour le traitement du cancer et l'induction sélective d'apoptose dans des cellules. L'invention concerne en outre des composés associés à la modification des procaspases telle que la procaspase 3. Selon certains modes de réalisation, l'invention concerne des compositions capables d'activation de la procaspase 3.