quinoline-2-carboxaldehyde-2-pyridylhydrazone | 16085-59-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: quinoline-2-carboxaldehyde-2-pyridylhydrazone
• 英文别名: 2-Quinolinecarboxaldehyde 2-pyridylhydrazone；N-(quinolin-2-ylmethylideneamino)pyridin-2-amine
• CAS: 16085-59-9
• 化学式: C₁₅H₁₂N₄
• 分子量: 248.287
• InChiKey: XOPZJFMYXOKWPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  sodium tetrachloropalladate(II) 、 quinoline-2-carboxaldehyde-2-pyridylhydrazone 以 甲醇 为溶剂， 以89%的产率得到quinoline-2-carboxaldehyde-2-pyridylhydrazone
  参考文献：
  名称：

  Spectroscopic, cytotoxic and DFT studies of a luminescent palladium(II) complex of a hydrazone ligand that induces apoptosis in human prostate cancer cells

  摘要：

  A luminescent palladium(II) complex [Pd(L)Cl], 1a was synthesized with the acyclic tridentate quinoline-2-carboxaldehyde-2-pyridylhydrazone ligand, HL, 1. The ligand, 1 showed a selective chromogenic behavior towards Pd2+ by changing the color of the solution from yellow to blue-violet, which can easily be detected by the naked-eye. DFT and TDDFT calculations were performed to determine the geometry optimized structures of the ligand 1 and the complex 1a as well as to correlate the electronic transitions. The complex 1a exhibits strong interaction towards DNA as revealed from K-b (intrinsic binding constant) and K-sq (Stern Volmer quenching constant) values, which are 1.47 x 10(5) M-1 and 5.67, respectively. The cytotoxicity of 1a has been examined with human prostate cancer cells (PC-3) and the sub-lethal dose (8 mu M) determined by dose-dependence studies. The relative degree of apoptotic and necrotic cell death using a sub-lethal dose were measured by flow cytometry. The cell cycle analysis shows that the complex 1a exhibits effective cell growth inhibition by triggering G2/M phase arrest and apoptosis in cancer cells. Moreover, its treatment triggers the mitochondrial pathway resulting in cytochrome c release and caspase-3 activation. (C) 2011 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2011.03.048