(E)-N'-(2,4,6-trimethylbenzylidene)isonicotinohydrazide | 1290139-00-2

• 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'-(2,4,6-trimethylbenzylidene)isonicotinohydrazide
• 英文别名: N'-(mesitylmethylene)isonicotinohydrazide；N-[(E)-(2,4,6-trimethylphenyl)methylideneamino]pyridine-4-carboxamide
• CAS: 1290139-00-2
• 化学式: C₁₆H₁₇N₃O
• 分子量: 267.33
• InChiKey: BKAZOJCNGPCUGN-VCHYOVAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  异烟肼 、 2,4,6-三甲基苯甲醛 以 乙醇 、 水 为溶剂， 以68%的产率得到(E)-N'-(2,4,6-trimethylbenzylidene)isonicotinohydrazide
  参考文献：
  名称：

  Synthesis and evaluation of isonicotinoyl hydrazone derivatives as antimycobacterial and anticancer agents

  摘要：

  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.

  DOI：

  10.1007/s00044-013-0632-2

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.