1-methyl-5-trifluoromethoxy-1H-indole-2,3-dione 3-(N-methylthiosemicarbazone) | 1084893-17-3

• 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: 1-methyl-5-trifluoromethoxy-1H-indole-2,3-dione 3-(N-methylthiosemicarbazone)
• 英文别名: 1-methyl-3-[[1-methyl-2-oxo-5-(trifluoromethoxy)indol-3-ylidene]amino]thiourea
• CAS: 1084893-17-3
• 化学式: C₁₂H₁₁F₃N₄O₂S
• 分子量: 332.306
• InChiKey: RZGZFHKSZPJINY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.36
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  65.96
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  4-甲基氨基硫脲 、 1-methyl-5-(trifluoromethoxy)indoline-2,3-dione 在 硫酸 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以82%的产率得到1-methyl-5-trifluoromethoxy-1H-indole-2,3-dione 3-(N-methylthiosemicarbazone)
  参考文献：
  名称：

  Synthesis and antituberculosis activity of 5-methyl/trifluoromethoxy-1H-indole-2,3-dione 3-thiosemicarbazone derivatives

  摘要：

  New series of 5-methyl/trifluoromethoxy-1H-indole-2,3-dione 3-thiosemicarbazones 3a-t, 1-methyl-5-methyl/trifluoromethoxy-1H-indole-2,3-dione 3-thiosemicarbazones 4a-y and 5-trifluoromethoxy-1-morpholinomethyl-1H-indole-2,3-dione 3-thiosemicarbazones 5a-m were synthesized. The structures of the synthesized compounds were confirmed by spectral data and elemental analysis. The new 5-methyl/trifluoromethoxy-1H-indole-2,3-dione derivatives, along with previously synthesized 5-methyl-1H-indole-2,3-dione 3-thiosemicarbazones 6a-1, were evaluated for in vitro antituberculosis activity against Mycobacterium tuberculosis H37Rv. 5-Methyl-1H-indole-2,3-dione 3-thiosemicarbazones (3b, 3d, 3f, 6c, 6d, and 6f), 5-trifluoromethoxy-1H-indole-2,3-dione 3-thiosemicarbazones (3q-s) and 5-trifluoromethoxy-1-morpholinomethyl-1H-indole-2,3-dione 3-thiosemicarbazones (5e and 5j-1) were found to be the most potent inhibitors of M. tuberculosis growth described in this study. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.050