5-trifluoromethoxy-1H-indole-2,3-dione-3-(N-benzylthiosemicarbazone) | 1084892-99-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-trifluoromethoxy-1H-indole-2,3-dione-3-(N-benzylthiosemicarbazone)
• 英文别名: 1-benzyl-3-[[2-oxo-5-(trifluoromethoxy)indol-3-yl]amino]thiourea
• CAS: 1084892-99-8
• 化学式: C₁₇H₁₃F₃N₄O₂S
• 分子量: 394.377
• InChiKey: OVBKHPUUGWCGQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  74.75
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  吗啉 、 聚合甲醛 、 5-trifluoromethoxy-1H-indole-2,3-dione-3-(N-benzylthiosemicarbazone) 以 乙醇 为溶剂， 反应 10.0h， 以91%的产率得到5-trifluoromethoxy-1-(morpholin-4-ylmethyl)-1H-indole-2,3-dione 3-(N-benzylthiosemicarbazone)
  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
• 作为产物：
  描述：

  异硫氰酸苯甲酯 在 硫酸 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 5-trifluoromethoxy-1H-indole-2,3-dione-3-(N-benzylthiosemicarbazone)
  参考文献：
  名称：

  Three novel compounds of 5-trifluoromethoxy-1H-indole-2,3-dione 3-thiosemicarbazone: Synthesis, crystal structures and molecular interactions

  摘要：

  5-Trifluoromethoxy-1H-indole-2,3-dione 3-(N-ethyl/benzylthiosemicarbazone) (2a/2b) and 5-trifluoromethoxy-1-morpholinomethyl-1H-indole-2,3-dione 3-(N-ethylthiosemicarbazone) (3a) were synthesized. The structures of the compounds were confirmed by elemental analysis, spectral data and X-ray single crystal diffraction analysis. The morpholin ring which adopts chair conformation and ethylamino group of 3a are disordered over two sets of sites with unequal occupancy. The indole heterocycle is nearly planar and the dihedral angle between the pyrrole and the adjacent phenyl ring is 2.09 degrees (in 2a), 4.61 degrees (in 2b) and 2.16 degrees (in 3a). In all three crystal structures, a strong N-H center dot center dot center dot O hydrogen bond links the flat conjugated H-N-N=C-C=O fragment into a six-membered ring. The molecules 2a, 2b and 3a have potential groups of proton donors (thiosemicarbazone group) available for hydrogen bonding. The structures 2b and 3a consist of isolated molecules, while that of 2a contains dimers formed by C-H center dot center dot center dot O hydrogen bonds. The molecules are linked into three dimensional framework structure by a combination of mainly N-H center dot center dot center dot N and N-H center dot center dot center dot O hydrogen bonds and weak C-F center dot center dot center dot pi and pi center dot center dot center dot pi interactions. (c) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2013.06.039

文献信息

• Synthesis and antituberculosis activity of 5-methyl/trifluoromethoxy-1H-indole-2,3-dione 3-thiosemicarbazone derivatives
  作者：Özlen Güzel、Nilgün Karalı、Aydın Salman

  DOI：10.1016/j.bmc.2008.08.050

  日期：2008.10

  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.
• Three novel compounds of 5-trifluoromethoxy-1H-indole-2,3-dione 3-thiosemicarbazone: Synthesis, crystal structures and molecular interactions
  作者：Filiz Betül Kaynak、Süheyla Özbey、Nilgün Karalı

  DOI：10.1016/j.molstruc.2013.06.039

  日期：2013.10

  5-Trifluoromethoxy-1H-indole-2,3-dione 3-(N-ethyl/benzylthiosemicarbazone) (2a/2b) and 5-trifluoromethoxy-1-morpholinomethyl-1H-indole-2,3-dione 3-(N-ethylthiosemicarbazone) (3a) were synthesized. The structures of the compounds were confirmed by elemental analysis, spectral data and X-ray single crystal diffraction analysis. The morpholin ring which adopts chair conformation and ethylamino group of 3a are disordered over two sets of sites with unequal occupancy. The indole heterocycle is nearly planar and the dihedral angle between the pyrrole and the adjacent phenyl ring is 2.09 degrees (in 2a), 4.61 degrees (in 2b) and 2.16 degrees (in 3a). In all three crystal structures, a strong N-H center dot center dot center dot O hydrogen bond links the flat conjugated H-N-N=C-C=O fragment into a six-membered ring. The molecules 2a, 2b and 3a have potential groups of proton donors (thiosemicarbazone group) available for hydrogen bonding. The structures 2b and 3a consist of isolated molecules, while that of 2a contains dimers formed by C-H center dot center dot center dot O hydrogen bonds. The molecules are linked into three dimensional framework structure by a combination of mainly N-H center dot center dot center dot N and N-H center dot center dot center dot O hydrogen bonds and weak C-F center dot center dot center dot pi and pi center dot center dot center dot pi interactions. (c) 2013 Elsevier B.V. All rights reserved.