2-hydroxy-N'-[1-(2-hydroxynaphthyl)ethylidene]benzohydrazide | 1403612-04-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-hydroxy-N'-[1-(2-hydroxynaphthyl)ethylidene]benzohydrazide
• 英文别名: 2-hydroxy-1-acetonaphthone salicylhydrazone；2-hydroxy-N-[1-(2-hydroxynaphthalen-1-yl)ethylideneamino]benzamide
• CAS: 1403612-04-3
• 化学式: C₁₉H₁₆N₂O₃
• 分子量: 320.348
• InChiKey: YOABGLBICQPTKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  81.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  bis(acetylacetonate)oxovanadium 、 2-hydroxy-N'-[1-(2-hydroxynaphthyl)ethylidene]benzohydrazide 以 乙醇 为溶剂， 反应 3.0h， 以65%的产率得到
  参考文献：
  名称：

  Highly Stable Hexacoordinated Nonoxidovanadium(IV) Complexes of Sterically Constrained Ligands: Syntheses, Structure, and Study of Antiproliferative and Insulin Mimetic Activity

  摘要：

  Three highly stable, hexacoordinated nonoxidovanadium(IV), V-IV(L)(2), complexes (1-3) have been isolated and structurally characterized with tridentate aroylhydrazonates containing ONO donor atoms. All the complexes are stable in the open air in the solid state as well as in solution, a phenomenon rarely observed in nonoxidovanadium(IV) complexes. The complexes have good solubility in organic solvents, permitting electrochemical and various spectroscopic investigations. The existence of nonoxidovanadium(IV) complexes was confirmed by elemental analysis, ESI mass spectroscopy, cyclic voltammetry, EPR, and magnetic susceptibility measurements. X-ray crystallography showed the N3O3 donor set to define a trigonal prismatic geometry in each case. All the complexes show in vitro insulin mimetic activity against insulin responsive L6 myoblast cells, with complex 3 being the most potent, which is comparable to insulin at the complex concentration of 4 mu M, while the others have moderate insulin mimetic activity. In addition, the in vitro antiproliferative activity of complexes 1-3 against the He La cell line was assayed. The cytotoxicity of the complexes is affected by the various functional groups attached to the bezoylhydrazone derivative and 2 showed considerable antiproliferative activity compared to the most commonly used chemotherapeutic drugs.

  DOI：

  10.1021/ic401866x
• 作为产物：
  描述：

  1-乙酰基-2-萘酚 、 水杨酰肼 以 乙醇 为溶剂， 以60%的产率得到2-hydroxy-N'-[1-(2-hydroxynaphthyl)ethylidene]benzohydrazide
  参考文献：
  名称：

  Highly Stable Hexacoordinated Nonoxidovanadium(IV) Complexes of Sterically Constrained Ligands: Syntheses, Structure, and Study of Antiproliferative and Insulin Mimetic Activity

  摘要：

  Three highly stable, hexacoordinated nonoxidovanadium(IV), V-IV(L)(2), complexes (1-3) have been isolated and structurally characterized with tridentate aroylhydrazonates containing ONO donor atoms. All the complexes are stable in the open air in the solid state as well as in solution, a phenomenon rarely observed in nonoxidovanadium(IV) complexes. The complexes have good solubility in organic solvents, permitting electrochemical and various spectroscopic investigations. The existence of nonoxidovanadium(IV) complexes was confirmed by elemental analysis, ESI mass spectroscopy, cyclic voltammetry, EPR, and magnetic susceptibility measurements. X-ray crystallography showed the N3O3 donor set to define a trigonal prismatic geometry in each case. All the complexes show in vitro insulin mimetic activity against insulin responsive L6 myoblast cells, with complex 3 being the most potent, which is comparable to insulin at the complex concentration of 4 mu M, while the others have moderate insulin mimetic activity. In addition, the in vitro antiproliferative activity of complexes 1-3 against the He La cell line was assayed. The cytotoxicity of the complexes is affected by the various functional groups attached to the bezoylhydrazone derivative and 2 showed considerable antiproliferative activity compared to the most commonly used chemotherapeutic drugs.

  DOI：

  10.1021/ic401866x

文献信息

• Syntheses and crystal structures of oxovanadium(V) complexes derived from N′-[1-(2-hydroxynaphthyl)ethylidene]-4-nitrobenzohydrazide and 2-hydroxy-N′-[1-(2-hydroxynaphthyl)ethylidene]benzohydrazide
  作者：C. L. Yuan

  DOI：10.1134/s1070328412070111

  日期：2012.8

  Reactions of bis(acetylacetonato)oxovanadium(IV) with N'-[1-(2-hydroxynaphthyl)ethylidene]-4-nitrobenzohydrazide (H2HNB) and 2-hydroxy-N'-[1-(2-hydroxynaphthyl)ethylidene]benzohydrazide (H2HHB), respectively, product two oxovanadium(V) species with the formulas [VO(OMe)(HNB)](2) (I) and [VO(OMe)(HHB)] (II). The complexes I and II have been characterized by elemental analysis, IR spectra, and single crystal X-ray diffraction. The crystal of I is monoclinic: space group P2(1)/n, a = 8.208(2), b = 14.528(3), c = 16.418(3) , beta = 97.887(3)A degrees, V = 1939.3(7) (3), Z = 2. The crystal of II is triclinic: space group P a = 8.334(2), b = 10.236(2), c = 11.337(2) , alpha = 80.91(3)A degrees, beta = 75.41(3)A degrees, I" = 75.63(3)A degrees, V = 902.0(3) (3), Z = 2. Complex I is a methoxide-bridged dimeric oxovanadium(V) complex, and complex II is a mononuclear oxovanadium(V) complex. The V atom in I is in an octahedral coordination, and that in II is in a square pyramidal coordination.