4-(2-fluorophenyl)-1-(indol-2-yl)-carbonylthiosemicarbazide | 1346176-62-2

• 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: 4-(2-fluorophenyl)-1-(indol-2-yl)-carbonylthiosemicarbazide
• 英文别名: 1-(2-fluorophenyl)-3-(1H-indole-2-carbonylamino)thiourea
• CAS: 1346176-62-2
• 化学式: C₁₆H₁₃FN₄OS
• 分子量: 328.37
• InChiKey: NOYYDENCABIMDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  101
• 氢给体数：
  4
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1H-吲哚-2-羧酸肼 、 异硫氰酸(2-氟苯)酯 反应 12.0h， 生成 4-(2-fluorophenyl)-1-(indol-2-yl)-carbonylthiosemicarbazide
  参考文献：
  名称：

  Synthesis and structure–activity relationship studies of 4-arylthiosemicarbazides as topoisomerase IV inhibitors with Gram-positive antibacterial activity. Search for molecular basis of antibacterial activity of thiosemicarbazides

  摘要：

  1-(indol-2-carbonyl)-4-(4-nitrophenyl)-thiosemicarbazide was synthesized and antibacterial and type IIA topoisomerases (DNA gyrase and topoisomerase IV) activity was evaluated. It was found that it shows activity against Gram-positive bacteria with MICs of 50 mu g/mL and inhibitory action against topoisomerase IV with an IC50 of 14 mu M. Although modification of its structure resulted in molecules with a lower biological profile, our observations strongly implicate that thiosemicarbazide derivatives participate in at least two different mechanisms of antibacterial activity; one is connected with the inhibition of topoisomerase IV, while the nature of the other cannot be elucidated from the limited data collected thus far. The differences in bioactivity further investigated by the molecular modeling approach and docking studies suggest that inhibitory activity of 4-arylthiosemicarbazides is connected with electronic structure rather than the geometry of the molecule. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.09.034

文献信息

• Synthesis and structure–activity relationship studies of 4-arylthiosemicarbazides as topoisomerase IV inhibitors with Gram-positive antibacterial activity. Search for molecular basis of antibacterial activity of thiosemicarbazides
  作者：Agata Siwek、Paweł Stączek、Joanna Stefańska

  DOI：10.1016/j.ejmech.2011.09.034

  日期：2011.11

  1-(indol-2-carbonyl)-4-(4-nitrophenyl)-thiosemicarbazide was synthesized and antibacterial and type IIA topoisomerases (DNA gyrase and topoisomerase IV) activity was evaluated. It was found that it shows activity against Gram-positive bacteria with MICs of 50 mu g/mL and inhibitory action against topoisomerase IV with an IC50 of 14 mu M. Although modification of its structure resulted in molecules with a lower biological profile, our observations strongly implicate that thiosemicarbazide derivatives participate in at least two different mechanisms of antibacterial activity; one is connected with the inhibition of topoisomerase IV, while the nature of the other cannot be elucidated from the limited data collected thus far. The differences in bioactivity further investigated by the molecular modeling approach and docking studies suggest that inhibitory activity of 4-arylthiosemicarbazides is connected with electronic structure rather than the geometry of the molecule. (C) 2011 Elsevier Masson SAS. All rights reserved.