4-(tricyclo[3.3.1.1^3,7]dec-1-yl)-N'-[3-(trifluoromethyl)benzoyl]quinoline-2-carbohydrazide | 1621608-04-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-(tricyclo[3.3.1.1^3,7]dec-1-yl)-N'-[3-(trifluoromethyl)benzoyl]quinoline-2-carbohydrazide
• 英文别名: 4-(1-adamantyl)-N'-[3-(trifluoromethyl)benzoyl]quinoline-2-carbohydrazide
• CAS: 1621608-04-5
• 化学式: C₂₈H₂₆F₃N₃O₂
• 分子量: 493.529
• InChiKey: NZOZWHRECMDGNN-UHFFFAOYSA-N

物化性质

• 熔点：
  184-187 °C
• 沸点：
  697.564±55.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.342±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  36
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  71.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  methyl 4-(1-adamantyl)-2-quinolinecarboxylate 在 一水合肼 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 4-(tricyclo[3.3.1.1^3,7]dec-1-yl)-N'-[3-(trifluoromethyl)benzoyl]quinoline-2-carbohydrazide
  参考文献：
  名称：

  Synthesis, biological evaluation and 3D-QSAR study of hydrazide, semicarbazide and thiosemicarbazide derivatives of 4-(adamantan-1-yl)quinoline as anti-tuberculosis agents

  摘要：

  We report synthesis, anti-tuberculosis activity and 3D-QSAR study of forty nine hydrazide, semicarbazide and thiosemicarbazide derivatives of 4-(adamantan-1-yl)quinoline. The most potent compounds upon evaluation for anti-tuberculosis activity exhibited MIC99 of 3.125 mu g/mL against Mycobacterium tuberculosis H37Rv strain. We applied the in silica technique of 3D-QSAR to study structure activity relationship of the synthesized compounds. The developed CoMFA model exhibited excellent r(ncv)(2) of 0.971, and r(cv)(2) of 0.543. The predicted r(pred)(2) of 0.883 showed that the predicted values were in good agreement with the experimental values. Further, the contour map analysis, suggested that the sterically bulky and electronegative substitutions at the para position of the phenyl ring are favorable for anti-tuberculosis activity. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.07.100

文献信息

• Synthesis, biological evaluation and 3D-QSAR study of hydrazide, semicarbazide and thiosemicarbazide derivatives of 4-(adamantan-1-yl)quinoline as anti-tuberculosis agents
  作者：Sanjay R. Patel、Rahul Gangwal、Abhay T. Sangamwar、Rahul Jain

  DOI：10.1016/j.ejmech.2014.07.100

  日期：2014.10

  We report synthesis, anti-tuberculosis activity and 3D-QSAR study of forty nine hydrazide, semicarbazide and thiosemicarbazide derivatives of 4-(adamantan-1-yl)quinoline. The most potent compounds upon evaluation for anti-tuberculosis activity exhibited MIC99 of 3.125 mu g/mL against Mycobacterium tuberculosis H37Rv strain. We applied the in silica technique of 3D-QSAR to study structure activity relationship of the synthesized compounds. The developed CoMFA model exhibited excellent r(ncv)(2) of 0.971, and r(cv)(2) of 0.543. The predicted r(pred)(2) of 0.883 showed that the predicted values were in good agreement with the experimental values. Further, the contour map analysis, suggested that the sterically bulky and electronegative substitutions at the para position of the phenyl ring are favorable for anti-tuberculosis activity. (C) 2014 Elsevier Masson SAS. All rights reserved.