ethyl 2-(4-(4-cyanobenzyl)piperazin-1-yl)acetate | 1554476-56-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-(4-(4-cyanobenzyl)piperazin-1-yl)acetate
• 英文别名: ethyl 4-[(4-Cyanophenyl)methyl]-1-piperazineacetate；Ethyl 2-(4-(4-cyanobenzyl)piperazin-1-yl)acetate；ethyl 2-[4-[(4-cyanophenyl)methyl]piperazin-1-yl]acetate
• CAS: 1554476-56-0
• 化学式: C₁₆H₂₁N₃O₂
• 分子量: 287.362
• InChiKey: KQSAKOPGRAEDDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  56.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-(4-(4-cyanobenzyl)piperazin-1-yl)acetate 在 盐酸 、 肼 作用下， 以 乙醇 、 水 为溶剂， 生成 2-(4-(4-cyanobenzyl)piperazin-1-yl)-N'-(2-hydroxy-3-propylbenzylidene )acetohydrazide
  参考文献：
  名称：

  Removal of Metabolic Liabilities Enables Development of Derivatives of Procaspase-Activating Compound 1 (PAC-1) with Improved Pharmacokinetics

  摘要：

  Procaspase-activating compound 1 (PAC-1) is an o-hydroxy-N-acylhydrazone that induces apoptosis in cancer cells by chelation of labile inhibitory zinc from procaspase-3. PAC-1 has been assessed in a wide variety of cell culture experiments and in vivo models of cancer, with promising results, and a phase 1 clinical trial in cancer patients has been initiated (NCT02355535). For certain applications, however, the in vivo half-life of PAC-1 could be limiting. Thus, with the goal of developing a compound with enhanced metabolic stability, a series of PAC-1 analogues were designed containing modifications that systematically block sites of metabolic vulnerability. Evaluation of the library of compounds identified four potentially superior candidates with comparable anticancer activity in cell culture, enhanced metabolic stability in liver microsomes, and improved tolerability in mice. In head-to-head experiments with PAC-1, pharmacokinetic evaluation in mice demonstrated extended elimination half-lives and greater area under the curve values for each of the four compounds, suggesting them as promising candidates for further development.

  DOI：

  10.1021/acs.jmedchem.5b00413
• 作为产物：
  描述：

  对氰基溴化苄 、 1-(乙氧基羰甲基)哌嗪 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以92.3%的产率得到ethyl 2-(4-(4-cyanobenzyl)piperazin-1-yl)acetate
  参考文献：
  名称：

  [EN] ENZYME-ACTIVATING COMPOUNDS AND COMPOSITIONS
  [FR] COMPOSÉS ET COMPOSITIONS ACTIVANT DES ENZYMES

  摘要：

  这项发明提供了用于调节某些酶的化合物和组合物。这些化合物和组合物可以诱导细胞死亡，特别是癌细胞死亡。该发明还提供了合成和使用这些化合物和组合物的方法，包括在治疗癌症和选择性诱导细胞凋亡中使用这些化合物和组合物的方法。

  公开号：

  WO2014022858A1

文献信息

• [EN] ENZYME-ACTIVATING COMPOUNDS AND COMPOSITIONS<br/>[FR] COMPOSÉS ET COMPOSITIONS ACTIVANT DES ENZYMES
  申请人：HERGENROTHER PAUL J

  公开号：WO2014022858A1

  公开（公告）日：2014-02-06

  The invention provides compounds and compositions useful for the modulation of certain enzymes. The compounds and compositions can induce of cell death, particularly cancer cell death. The invention also provides methods for the synthesis and use of the compounds and compositions, including the use of compounds and compositions in therapy for the treatment of cancer and selective induction of apoptosis in cells.

  这项发明提供了用于调节某些酶的化合物和组合物。这些化合物和组合物可以诱导细胞死亡，特别是癌细胞死亡。该发明还提供了合成和使用这些化合物和组合物的方法，包括在治疗癌症和选择性诱导细胞凋亡中使用这些化合物和组合物的方法。
• Enzyme-activating compounds and compositions
  申请人：The Board of Trustees of the University of Illinois

  公开号：US09249116B2

  公开（公告）日：2016-02-02

  The invention provides compounds and compositions useful for the modulation of certain enzymes. The compounds and compositions can induce of cell death, particularly cancer cell death. The invention also provides methods for the synthesis and use of the compounds and compositions, including the use of compounds and compositions in therapy for the treatment of cancer and selective induction of apoptosis in cells.

  本发明提供了一些化合物和组合物，用于调节某些酶的作用。这些化合物和组合物可以诱导细胞死亡，特别是癌细胞死亡。本发明还提供了化合物和组合物的合成和使用方法，包括在治疗癌症和选择性诱导细胞凋亡中使用化合物和组合物的方法。
• ENZYME-ACTIVATING COMPOUNDS AND COMPOSITIONS
  申请人：The Board of Trustees of the University of Illinois

  公开号：US20160176833A1

  公开（公告）日：2016-06-23

  The invention provides compounds and compositions useful for the modulation of certain enzymes. The compounds and compositions can induce of cell death, particularly cancer cell death. The invention also provides methods for the synthesis and use of the compounds and compositions, including the use of compounds and compositions in therapy for the treatment of cancer and selective induction of apoptosis in cells.

  这项发明提供了用于调节某些酶的化合物和组合物。这些化合物和组合物可以诱导细胞死亡，特别是癌细胞死亡。该发明还提供了合成和使用这些化合物和组合物的方法，包括在治疗癌症和选择性诱导细胞凋亡中使用这些化合物和组合物的方法。
• PARTICULATE DRUG DELIVERY METHODS
  申请人：The Board of Trustees of the University of Illinois

  公开号：US20150210659A1

  公开（公告）日：2015-07-30

  The invention provides compounds and compositions useful for the modulation of certain enzymes. The compounds and compositions can induce of cell death, particularly cancer cell death. The invention also provides methods for the synthesis and use of the compounds and compositions, including the use of compounds and compositions in therapy for the treatment of cancer and selective induction of apoptosis in cells.

  本发明提供了可用于调节某些酶的化合物和组合物。这些化合物和组合物可以诱导细胞死亡，特别是癌细胞死亡。本发明还提供了合成和使用这些化合物和组合物的方法，包括在治疗癌症和选择性诱导细胞凋亡方面使用这些化合物和组合物的方法。
• US9249116B2
  申请人：——

  公开号：US9249116B2

  公开（公告）日：2016-02-02