(E)-N'-(2,3,4-trihydroxybenzylidene)isonicotinohydrazide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (E)-N'-(2,3,4-trihydroxybenzylidene)isonicotinohydrazide
• 英文别名: N-[(E)-(2,3,4-trihydroxyphenyl)methylideneamino]pyridine-4-carboxamide
• 化学式: C₁₃H₁₁N₃O₄
• 分子量: 273.248
• InChiKey: DIMCIEAWBXGIJV-VIZOYTHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 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：
  115
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  异烟酸甲酯 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 (E)-N'-(2,3,4-trihydroxybenzylidene)isonicotinohydrazide
  参考文献：
  名称：

  基于结构的新型己糖激酶2抑制剂的发现。

  摘要：

  Hexokinase 2（HK2）在大多数人类癌症中均过表达，并且已被证明是癌症治疗的有希望的靶标。在这项研究中，基于HK2的结构，我们筛选了超过600万种化合物以获得铅。然后设计，合成总共26种（E）-N'-（2,3,4-三羟基亚苄基）芳基酰肼衍生物，并评估其针对两种癌细胞系的HK2酶活性和IC50值。26种目标化合物中的大多数都具有出色的体外活性。其中，化合物3j对HK2酶活性的抑制作用最强，IC50为0.53±0.13μM，对SW480细胞的生长抑制作用最强，IC50为7.13±1.12μM，值得进一步研究。

  DOI：

  10.1016/j.bioorg.2020.103609

文献信息

• Synthesis and evaluation of isonicotinoyl hydrazone derivatives as antimycobacterial and anticancer agents
  作者：H. S. Naveen Kumar、Thaigarajan Parumasivam、Fatimah Jumaat、Pazilah Ibrahim、Mohd. Zaini Asmawi、Amirin Sadikun

  DOI：10.1007/s00044-013-0632-2

  日期：2014.1

  A new series of isonicotinoyl hydrazone derivatives (3a-3o) have been synthesized, characterized and evaluated for in vitro antimycobacterial activity against M. tuberculosis H37Rv and two clinical isolates using tetrazolium microplate assay (TEMA). Some of these compounds showed moderate to good antimycobacterial activity at micro molar concentrations. Among them, 3k and 3m were the most potent analogues with an inhibition concentration at 0.59 and 0.65 mu M, respectively, against M. tuberculosis H37Rv compared to parent drug, isoniazid (0.57 mu M). Additionally, all the synthesized compounds were subjected to in vitro anticancer activity against human colorectal cancer cell lines (HCT 116). Compounds 3b and 3l displayed antiproliferative activity at inhibitory concentration 3.1 and 0.29 mu M, respectively, when compared to standard, 5-fluorouracil (5 mu M). These results can be considered as an important start point for the rational design of new leads for antitubercular and anticancer drug discovery.
• Non-peptidyl agents with pHSP20-like activity, and uses thereof
  申请人：von Rechenberg Moritz

  公开号：US20090136561A1

  公开（公告）日：2009-05-28

  The present invention provides compositions and methods for modulating smooth muscle cells. The present invention also provides methods of identifying small molecule candidate therapeutic agents for modulating smooth muscle.