(E)-N'-(4-hydroxybenzylidene)-1H-indole-2-carbohydrazide

• 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: (E)-N'-(4-hydroxybenzylidene)-1H-indole-2-carbohydrazide
• 英文别名: N'-[(E)-(4-hydroxyphenyl)methylidene]-1H-indole-2-carbohydrazide；N-[(E)-(4-hydroxyphenyl)methylideneamino]-1H-indole-2-carboxamide
• 化学式: C₁₆H₁₃N₃O₂
• 分子量: 279.298
• InChiKey: SCLFZAPTLAZAEI-LICLKQGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 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 甲醇 为溶剂， 反应 9.0h， 生成 (E)-N'-(4-hydroxybenzylidene)-1H-indole-2-carbohydrazide
  参考文献：
  名称：

  Evaluation of 2-indolcarbohydrazones as potent α-glucosidase inhibitors, in silico studies and DFT based stereochemical predictions

  摘要：

  2-Indolcarbohydrazones 1-28 were synthesized and evaluated for their alpha-glucosidase inhibitory potential. A varying degree of inhibitory potential with IC50 values in the range of 2.3 +/- 0.11-226.4 +/- 6.8 mu M was observed while comparing these outcomes with the standard acarbose (IC50 = 906.0 +/- 6.3 mu M). The stereochemistry of ten (10) randomly selected compounds (1, 3, 6, 8, 12, 18, 19, 23, 25 and 28) was predicted by Density Functional Theory (DFT). The stability of E isomer was deduced by comparing the calculated and experimental vibration modes of nu(C=O), nu(N=C) and nu(CH) (CH in -N=CH-R). It was observed that except compound 18, all other compounds were deduced to have E configuration while molecular modeling studies revealed the key interactions between enzyme and synthesized compounds. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2015.09.001

文献信息

• Indole derivatives as multifunctional drugs: Synthesis and evaluation of antioxidant, photoprotective and antiproliferative activity of indole hydrazones
  作者：Monica Demurtas、Anna Baldisserotto、Ilaria Lampronti、Davide Moi、Gianfranco Balboni、Salvatore Pacifico、Silvia Vertuani、Stefano Manfredini、Valentina Onnis

  DOI：10.1016/j.bioorg.2019.02.007

  日期：2019.4

  erythroleukemia K562 and melanoma Colo-38 cells. Hydrazones 11, 16 and 17 showed growth inhibition at sub micromolar concentrations on both cell lines. These results indicate indole hydrazones as potential multifunctional molecules especially in the treatment of neoplastic diseases being the good antioxidant properties of 16 and 17 correlated to their high antiproliferative activity.

  容易制备两个系列的吲哚衍生物4-17、20-22，并分析它们的自由基清除能力。亚芳基-1H-吲哚-2-碳assay在DPPH，FRAP和ORAC分析中显示出不同程度的抗氧化活性。良好的抗氧化活性与亚芳基部分上羟基的数目和位置以及甲氧基或4-（二乙氨基）基团的存在有关。相反，异构体1H-吲哚-2-基（亚甲基）-苯并酰肼显示出较低的抗氧化剂活性。此外，与市售PBSA防晒滤光片相比，4-17显示出令人满意的体外SPF的光保护能力。显示最佳抗氧化剂和光防护特性的吲哚16和17被包含在不同的配方中，并对其局部释放进行了评估。改变配方成分 有可能优化皮肤吸附和活性吲哚在制剂中的溶解度。测试了azo4-17对人红白血病K562和黑素瘤Colo-38细胞的抗增殖作用。dRA 11、16和17在亚微摩尔浓度下在两种细胞系中均显示出生长抑制作用。这些结果表明吲哚酮是潜在的多功能分子，尤其是在治疗肿瘤疾病中，其