N'-[(2-hydroxyphenyl)methylidene]-1H-indole-2-carbohydrazide | 33521-35-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N'-[(2-hydroxyphenyl)methylidene]-1H-indole-2-carbohydrazide
• 英文别名: Salicylaldehyd-2-indoloylhydrazon；N'-(2-hydroxybenzylidene)-1h-indole-2-carbohydrazide；N-[(2-hydroxyphenyl)methylideneamino]-1H-indole-2-carboxamide
• CAS: 33521-35-6
• 化学式: C₁₆H₁₃N₃O₂
• 分子量: 279.298
• InChiKey: RWGDZRVPFFCMMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 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：
  77.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  吲哚-2-羧酸甲酯 在 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 N'-[(2-hydroxyphenyl)methylidene]-1H-indole-2-carbohydrazide
  参考文献：
  名称：

  Salicylaldehyde-indole-2-acylhydrazone: a simple, colorimetric and absorption ratiometric chemosensor for acetate ion

  摘要：

  A simple anion receptor (i.e. salicylaldehyde-indole-2-acylhydrazone) was synthesised and its recognition properties were investigated by naked-eye observation, UVvis titration spectra, 1H NMR spectroscopy and DFT calculations. The obtained results indicated that this receptor could realise the selective colorimetric sensing and absorption ratiometric response towards AcO in CH3CNDMSO medium, by virtue of threefold intermolecular hydrogen bonding interactions formed with phenolic OH, indole NH and amide NH.

  DOI：

  10.1080/10610278.2012.758368

文献信息

• Synthesis and antiproliferative activity of salicylidenehydrazones based on indole-2(3)-carboxylic acids
  作者：Andrey G. Vasin、Lyubov G. Dezhenkova、Ivan V. Ivanov、Alexander M. Scherbakov、Andrey E. Shchekotikhin

  DOI：10.1007/s10593-020-02724-2

  日期：2020.6

  A series of indole-2(3)-carboxylic acid hydrazones were synthesized and their antiproliferative activity was studied for the K562 leukemia, MCF7 breast adenocarcinoma, and HCT116 colon carcinoma cell lines and resistant HCT116p53KO subline in order to preliminary screen biological properties and to reveal the role of the aldehyde fragment and heterocycle in the ability of compounds to inhibit tumor

  合成了一系列吲哚-2（3）-羧酸，并对其在K562白血病，MCF7乳腺腺癌和HCT116结肠癌细胞系及耐药HCT116p53KO亚系中的抗增殖活性进行了初步筛选，以揭示其生物学特性。醛片段和杂环在化合物抑制肿瘤生长能力中的作用。已经鉴定出许多以亚微摩尔浓度抑制肿瘤细胞生长的衍生物，有望进一步优化和深入研究抗肿瘤特性。