N'-(2-hydroxybenzylidene)-3-hydroxylbenzohydrazide | 68406-66-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N'-(2-hydroxybenzylidene)-3-hydroxylbenzohydrazide
• 英文别名: 3-hydroxy-N-[(2-hydroxyphenyl)methylideneamino]benzamide
• CAS: 68406-66-6
• 化学式: C₁₄H₁₂N₂O₃
• mdl: MFCD00432655
• 分子量: 256.261
• InChiKey: XSZWDTHMORZIBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  甲醇 、 cobalt(II) nitrate hexahydrate 、 2,2'-联吡啶 、 N'-(2-hydroxybenzylidene)-3-hydroxylbenzohydrazide 、 sodium azide 反应 0.17h， 以50%的产率得到
  参考文献：
  名称：

  Synthesis, structures and urease inhibitory activity of cobalt(III) complexes with Schiff bases

  摘要：

  A series of new cobalt(III) complexes were prepared. They are [CoL1(py)(3)]center dot NO3 (1), [CoL2(bipy)(N-3)]center dot CH3OH (2), [CoL3(HL3)(N-3)]center dot NO3 (3), and [CoL4(MeOH)(N-3)] (4), where L-1, L-2, L-3 and L-4 are the deprotonated form of N'-(2- hydroxy-5-methoxybenzylidene)-3-methylbenzohydrazide, N'-(2-hydroxybenzylidene)-3-hydroxylbenzohydrazide, 2-[(2-dimethylaminoethylimino) methyl]-4-methylphenol, and N, N'-bis(5-methylsalicylidene)-o-phenylenediamine, respectively, py is pyridine, and bipy is 2,2'-bipyridine. The complexes were characterized by infrared and UV-Vis spectra, and single crystal X-ray diffraction. The Co atoms in the complexes are in octahedral coordination. Complexes 1 and 4 show effective urease inhibitory activities, with IC50 values of 4.27 and 0.35 mu mol L-1, respectively. Complex 2 has medium activity against urease, with IC50 value of 68.7 mu mol L-1. While complex 3 has no activity against urease. Molecular docking study of the complexes with Helicobacter pylori urease was performed. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.12.013
• 作为产物：
  描述：

  水杨醛 、 3-羟基苯酰肼 在 甲酸 作用下， 以 二甲基亚砜 为溶剂， 生成 N'-(2-hydroxybenzylidene)-3-hydroxylbenzohydrazide
  参考文献：
  名称：

  Mechanistic differences between in vitro assays for hydrazone-based small molecule inhibitors of anthrax lethal factor

  摘要：

  A systematically generated series of hydrazones were analyzed as potential inhibitors of anthrax lethal factor. The hydrazones were screened using one UV-based and two fluorescence-based in vitro assays. The study identified several inhibitors with IC50 values in the micromolar range, and importantly, significant differences in the types of inhibition were observed with the different assays. (c) 2006 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2006.07.004

文献信息

• Synthesis, structures and urease inhibitory activity of cobalt(III) complexes with Schiff bases
  作者：Changling Jing、Cunfang Wang、Kai Yan、Kedong Zhao、Guihua Sheng、Dan Qu、Fang Niu、Hailiang Zhu、Zhonglu You

  DOI：10.1016/j.bmc.2015.12.013

  日期：2016.1

  A series of new cobalt(III) complexes were prepared. They are [CoL1(py)(3)]center dot NO3 (1), [CoL2(bipy)(N-3)]center dot CH3OH (2), [CoL3(HL3)(N-3)]center dot NO3 (3), and [CoL4(MeOH)(N-3)] (4), where L-1, L-2, L-3 and L-4 are the deprotonated form of N'-(2- hydroxy-5-methoxybenzylidene)-3-methylbenzohydrazide, N'-(2-hydroxybenzylidene)-3-hydroxylbenzohydrazide, 2-[(2-dimethylaminoethylimino) methyl]-4-methylphenol, and N, N'-bis(5-methylsalicylidene)-o-phenylenediamine, respectively, py is pyridine, and bipy is 2,2'-bipyridine. The complexes were characterized by infrared and UV-Vis spectra, and single crystal X-ray diffraction. The Co atoms in the complexes are in octahedral coordination. Complexes 1 and 4 show effective urease inhibitory activities, with IC50 values of 4.27 and 0.35 mu mol L-1, respectively. Complex 2 has medium activity against urease, with IC50 value of 68.7 mu mol L-1. While complex 3 has no activity against urease. Molecular docking study of the complexes with Helicobacter pylori urease was performed. (C) 2015 Elsevier Ltd. All rights reserved.
• Mechanistic differences between in vitro assays for hydrazone-based small molecule inhibitors of anthrax lethal factor
  作者：M. Leslie Hanna、Theodore M. Tarasow、Julie Perkins

  DOI：10.1016/j.bioorg.2006.07.004

  日期：2007.2

  A systematically generated series of hydrazones were analyzed as potential inhibitors of anthrax lethal factor. The hydrazones were screened using one UV-based and two fluorescence-based in vitro assays. The study identified several inhibitors with IC50 values in the micromolar range, and importantly, significant differences in the types of inhibition were observed with the different assays. (c) 2006 Elsevier Inc. All rights reserved.