4-chloro-2-{[2-(2-hydroxyethylamino)ethylimino]methyl}phenol | 1262029-63-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-chloro-2-{[2-(2-hydroxyethylamino)ethylimino]methyl}phenol
• 英文别名: 4-chloro-6-[[2-(2-hydroxyethylamino)ethylimino]methyl]phenol；4-Chloro-2-[2-(2-hydroxyethylamino)ethyliminomethyl]phenol
• CAS: 1262029-63-9
• 化学式: C₁₁H₁₅ClN₂O₂
• 分子量: 242.705
• InChiKey: ZFSAWWFSQKEOJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  64.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-chloro-2-{[2-(2-hydroxyethylamino)ethylimino]methyl}phenol 、 bis(acetylacetonato) oxovanadium(IV) 以 甲醇 为溶剂， 以67%的产率得到bis(μ2-oxo)bis(4-chloro-2-[[2-(2-hydroxyethylamino)ethylimino]methyl]phenoato)dioxovanadium(V)
  参考文献：
  名称：

  Synthesis, structures, and urease inhibitory activities of oxovanadium(V) complexes with Schiff bases

  摘要：

  A series of oxovanadium(V) complexes, [VO2L1](2) (1), [VO2L2](2) (2), [VO2L3](2) (3), [VO2L4](2) (4), [VO(OCH3)L-5] (5), and [VO(OCH3)(HOCH3)L-6] (6) (HL1 = 2-ethoxy-6-{[2-(2-hydroxyethylamino)ethylimino]methyl} phenol, HL2 = 4-chloro-2-{[2-(2-hydroxyethylamino)ethylimino]methyl}phenol, HL3 = 2-methoxy-6-[(2-methylaminoethylimino)methyl]phenol, HL4 = 4-chloro-2-[(2-methylaminoethylimino) methyl] phenol, HL5 = N'-(2-hydroxy-3-ethoxybenzylidene)-3-hydroxy-2-naphthohydrazide, and HL6 = N'-(2-hydroxy-5-chlorobenzylidene)-3-hydroxy-2-naphthohydrazide), have been prepared and structurally characterized by physico-chemical methods and X-ray diffraction. The inhibition rates (%) with the concentration of 100 mu M for the complexes on Helicobacter pylori urease are 18.96 +/- 0.44 (1), 33.01 +/- 1.80 (2), 35.83 +/- 0.78 (3), 48.09 +/- 1.23 (4), 45.91 +/- 2.09 (5), and 90.72 +/- 1.91 (6). The relationship between the structures and urease inhibitory activities indicates that the chloro-substituted complexes have stronger activity than the alk-oxy-substituted complexes. It is notable that one of the chloro-substituted complexes has very strong urease inhibitory activity, with IC50 value of 17.35 +/- 1.01 mu M, which is much lower than that of the acetohydroxamic acid coassayed as a standard urease inhibitor. The kinetic studies reveal that the complex is a mixed-competitive inhibitor of urease. The molecular docking study of the complexes with the Helicobacter pylori urease was performed. (C) 2011 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2011.11.039
• 作为产物：
  描述：

  羟乙基乙二胺 、 5-氯代水杨醛 以 甲醇 为溶剂， 反应 0.5h， 以93%的产率得到4-chloro-2-{[2-(2-hydroxyethylamino)ethylimino]methyl}phenol
  参考文献：
  名称：

  Synthesis, Characterization, and Crystal Structure of a Dinuclear Cadmium(II) Complex Derived From 4-Chloro-2-{[2-(2-Hydroxyethylamino)Ethylimino]Methyl}Phenol

  摘要：

  A phenolic O-bridged centrosymmetric dinuclear cadmium(II) complex, [Cd2L2(NO3)(2)]center dot 2MeOH, where L is the deprotonated form of 4-chloro-2-{[2-(2-hydroxyethylamino)ethylimino]methyl}phenol (HL), was synthesized and characterized by elemental analysis, IR spectra, and single-crystal X-ray diffraction. The crystal of the complex is monoclinic: space group P2(1)/c, a = 11.536(2), b = 9.657(2), c = 15.698(2) angstrom, beta = 106.742(2)degrees, V = 1674.7(4) angstrom(3), Z = 2. The inversion center of the complex is located at the midpoint of the two Cd atoms. Each Cd atom is in an octahedral coordination. In the crystal structure, the methanol molecules are linked to the cadmium complex molecules through intermolecular O-H center dot center dot center dot O hydrogen bonds.

  DOI：

  10.1080/15533174.2013.799494

文献信息

• Effect of the chloro-substitution on lowering diabetic hyperglycemia of vanadium complexes with their permeability and cytotoxicity
  作者：Ming-Jin Xie、Yan-Fen Niu、Xiao-Da Yang、Wei-Ping Liu、Ling Li、Li-Hui Gao、Shi-Ping Yan、Zhao-Hui Meng

  DOI：10.1016/j.ejmech.2010.10.013

  日期：2010.12

  The effect of the chloro-substitution of dinuclear vanadium (V) complexes on lowering diabetic hyperglycemia was evaluated. The in vivo tests for hypoglycemic activity show that complex 2 at the dose of 10.0 and 20.0 mg V kg(-1), could significantly decrease the blood glucose level. Importantly, our results the chloro substituent increased the insulin-enhancing properties of the complex 2. The two vanadium compounds had permeability above 10(-5) cm/s. It suggested that two complexes permeate via a passive diffusion mechanism. It was also suggested that two complexes has better good lipophilic properties. The cytotoxicity of two complexes on Caco-2 cells suggested the chlorine atom at C4 of complex 2 increased cytotoxicity for vanadium complexes. (C) 2010 Elsevier Masson SAS. All rights reserved.