2-[2-(pyrazol-1-yl)ethyliminomethyl]phenol | 1163138-89-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-[2-(pyrazol-1-yl)ethyliminomethyl]phenol
• 英文别名: 2-(2-Pyrazol-1-ylethyliminomethyl)phenol
• CAS: 1163138-89-3
• 化学式: C₁₂H₁₃N₃O
• 分子量: 215.255
• InChiKey: QUTBAGWCLPXSEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[2-(pyrazol-1-yl)ethyliminomethyl]phenol 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 2-[2-(pyrazol-1-yl)ethylaminomethyl]phenol
  参考文献：
  名称：

  Synthesis, characterization and cytotoxic activity of gallium(III) complexes anchored by tridentate pyrazole-based ligands

  摘要：

  Reactions of GaCl3 with pyrazole-containing ligands of the pyrazole-imine-phenol (HL1-HL3) or pyrazole-amine-phenol (HL4-HL6) types led to the synthesis of well-defined [GaL2](+) homoleptic complexes (1-6). Complexes 1-6 were characterized by elemental analysis, ESI-MS (electrospray ionization-mass spectrometry), IR and NMR spectroscopies, and in the case of Complex 1 also by X-ray diffraction analysis. In complexes 1-3, the pyrazole-imine-phenolate ligands act as monoanionic chelators that coordinate to the metal in a meridional fashion, while 4-6 contain monoanionic and facially coordinated pyrazole-amine-phenolate ligands. Complexes 1-3 have a greater stability in solution compared to 4-6, which have shown a more pronounced tendency to release the respective ancillary ligands. The cytotoxicity of 1-6 and of the respective ligands (HL1-HL6) was evaluated against human prostate cancer cells PC-3 and human breast cancer cells MCF-7. The substituents of the phenolate rings strongly influenced the cytotoxicity of the compounds. Complexes 3 and 6 that contain chloride substituents at the phenolate rings have shown the highest cytotoxicity, including in the cisplatin-resistant PC-3 cell line. The cytotoxic profile of 3 and 6 is very similar to the one displayed by the respective anchor ligands, respectively HL1 and HL6. The cytotoxic activity of 3 and 6 is slightly increased by the presence of transferrin, and both complexes provoke cell death mainly by induction of apoptotic pathways. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2010.01.003
• 作为产物：
  描述：

  2-吡唑-1-基乙胺 、 水杨醛 以 乙醇 为溶剂， 反应 2.0h， 生成 2-[2-(pyrazol-1-yl)ethyliminomethyl]phenol
  参考文献：
  名称：

  Synthesis, characterization and cytotoxic activity of gallium(III) complexes anchored by tridentate pyrazole-based ligands

  摘要：

  Reactions of GaCl3 with pyrazole-containing ligands of the pyrazole-imine-phenol (HL1-HL3) or pyrazole-amine-phenol (HL4-HL6) types led to the synthesis of well-defined [GaL2](+) homoleptic complexes (1-6). Complexes 1-6 were characterized by elemental analysis, ESI-MS (electrospray ionization-mass spectrometry), IR and NMR spectroscopies, and in the case of Complex 1 also by X-ray diffraction analysis. In complexes 1-3, the pyrazole-imine-phenolate ligands act as monoanionic chelators that coordinate to the metal in a meridional fashion, while 4-6 contain monoanionic and facially coordinated pyrazole-amine-phenolate ligands. Complexes 1-3 have a greater stability in solution compared to 4-6, which have shown a more pronounced tendency to release the respective ancillary ligands. The cytotoxicity of 1-6 and of the respective ligands (HL1-HL6) was evaluated against human prostate cancer cells PC-3 and human breast cancer cells MCF-7. The substituents of the phenolate rings strongly influenced the cytotoxicity of the compounds. Complexes 3 and 6 that contain chloride substituents at the phenolate rings have shown the highest cytotoxicity, including in the cisplatin-resistant PC-3 cell line. The cytotoxic profile of 3 and 6 is very similar to the one displayed by the respective anchor ligands, respectively HL1 and HL6. The cytotoxic activity of 3 and 6 is slightly increased by the presence of transferrin, and both complexes provoke cell death mainly by induction of apoptotic pathways. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2010.01.003

文献信息

• Synthesis and structural studies of mixed-ligand rhenium(V) complexes anchored by tridentate pyrazole-based ligands
  作者：Margarida Videira、Francisco Silva、António Paulo、Isabel C. Santos、Isabel Santos

  DOI：10.1016/j.ica.2008.12.032

  日期：2009.6

  The novel oxorhenium dichlorides mer-[ReO(L1)Cl-2] (1) and fac-[ReO(L2)Cl-2] (2) (L1 = 2-[2-(pyrazol-1-yl)ethyliminomethyl]phenolate; L2 = 2-[2-(pyrazol-1-yl)ethylaminomethyl]phenolate) were synthesized by reacting [NBu4][ReOCl4] with L1H and L2H, respectively. X-ray structural analysis of 1 and 2 has shown that L1 and L2 act as (N,N,O)-tridentate chelators coordinating to the Re(V) centre in a meridional and in a facial fashion, respectively. The reactivity of 2 towards potential bidentate/dianionic substrates is strongly dependent on the donor atom set, being observed that the presence of sulphur favours the displacement of the ancillary ligand (L2). By contrast, complex 2 reacted with (O,O)-bidentate substrates (1,2-ethanediol and oxalic acid) providing the mixed-ligand complexes fac-[ReO(L2)(OCH2CH2O)] (3) and fac-[ReO(L2)(C2O4)] (4). Complexes 3 and 4 are air and water-stable and have been characterized by the common spectroscopic techniques (IR, H-1 and C-13 NMR) and by X-ray diffraction analysis. (C) 2009 Published by Elsevier B.V.