4-phenyl-1-piperazineacetic acid salicylidenehydrazide | 127718-30-3

• 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: 4-phenyl-1-piperazineacetic acid salicylidenehydrazide
• CAS: 127718-30-3
• 化学式: C₁₉H₂₂N₄O₂
• 分子量: 338.409
• InChiKey: NXDUKQZBBNNMRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.66
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  68.17
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-phenyl-1-piperazineacetic acid salicylidenehydrazide 在 盐酸 、 硫酸 、 双氧水 、 iron(II) sulfate 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 2-(4-Chloro-phenyl)-5-(2-hydroxy-phenyl)-3-[2-(4-phenyl-piperazin-1-yl)-acetyl]-3H-tetrazol-2-ium; chloride
  参考文献：
  名称：

  Khanna; Saksena; Srivastava, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1990, vol. 29, # 1, p. 91 - 94

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 2-(4-phenylpiperazin-1-yl)acetate 在 一水合肼 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 生成 4-phenyl-1-piperazineacetic acid salicylidenehydrazide
  参考文献：
  名称：

  Piperazine clubbed with 2-azetidinone derivatives suppresses proliferation, migration and induces apoptosis in human cervical cancer HeLa cells through oxidative stress mediated intrinsic mitochondrial pathway

  摘要：

  Piperazine scaffolds or 2-azetidinone pharmacophores have been reported to show anti-cancer activities and apoptosis induction in different types of cancer cells. However, the mechanistic studies involve in induction of apoptosis addressing these two moieties for human cervical cancer cells remain uncertain. The present study emphasizes on the anti-proliferating properties and mechanism involved in induction of apoptosis for these structurally related azoles derivatives in HeLa cancer cells. 1-Phenylpiperazine clubbed with 2-azetidione derivatives (5a-5h) were synthesized, characterized using various spectroscopic techniques and evaluated for their in-vitro anti-proliferative activities and induction of apoptosis. Further, we also evaluated oxidative stress generated by these synthetic derivatives (5a-5h). Cell viability studies revealed that among all, the compound N-(3-chloro-2-(3-nitrophenyl)-4-oxoazetidin-1-yl)-2-(4-phenylpiperazin-1-yl) acetamide 5e remarkably inhibited the growth of HeLa cells in a concentration dependent manner having IC50 value of 29.44 +/- 1.46 A mu g/ml. Morphological changes, colonies suppression and inhibition of migration clearly showed the antineoplasicity in HeLa cells treated with 5e. Simultaneously, phosphatidylserine externalization, DNA fragmentation and cell-cycle arrest showed ongoing apoptosis in the HeLa cancer cells induced by compound 5e in concentration dependent manner. Additionally, generation of intracellular ROS along with the decrease in mitochondrial membrane potential supported that compound 5e caused oxidative stress resulting in apoptosis through mitochondria mediated pathway. Elevation in the level of cytochrome c and upregulation in expression of caspase-3 clearly indicated the involvement of the intrinsic pathway of programmed cell death. In brief; compound 5e could serve as a promising lead for the development of an effective antitumor agent.[GRAPHICS]

  DOI：

  10.1007/s10495-018-1439-x