4-nitro-indan-1-one thiosemicarbazone | 1350638-61-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 4-nitro-indan-1-one thiosemicarbazone
• 英文别名: [(4-nitro-2,3-dihydroinden-1-ylidene)amino]thiourea
• CAS: 1350638-61-7
• 化学式: C₁₀H₁₀N₄O₂S
• 分子量: 250.281
• InChiKey: PCFSKLSMECVSEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.08
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  93.55
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-nitro-indan-1-one thiosemicarbazone 、 2,4'-二氯苯乙酮 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.01h， 以91%的产率得到4-(4-chlorophenyl)-2-(2-(4-nitro-2,3-dihydro-1H-inden-1-ylidene)hydrazinyl)thiazolium chloride
  参考文献：
  名称：

  Synthesis and biological evaluation of some novel 1-indanone thiazolylhydrazone derivatives as anti-Trypanosoma cruzi agents

  摘要：

  A series of novel 4-arylthiazolylhydrazones (TZHs) derived from 1-indanones were synthesized in good yields (66-92%) in a simple procedure using microwave irradiation and then characterized by spectroscopy studies. The compounds were evaluated for their in vitro anti-Trypanosoma cruzi activity against the epimastigote, trypomastigote and amastigote forms of the parasite. Most TZHs displayed excellent activity, and were more potent and selective than the reference drug Benznidazole, used in the current chemotherapy. Analysis of the free sterols from parasite incubated with the compounds showed that inhibition of ergosterol biosynthesis is a possible target for the action of these new TZHs. In particular, TZH 9 emerged as a promising antichagasic compound to be evaluated in animal models. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.07.013
• 作为产物：
  描述：

  1-茚酮 在 硫酸 、 硝酸 作用下， 以 硝基甲烷 、 乙醇 为溶剂， 反应 1.25h， 生成 4-nitro-indan-1-one thiosemicarbazone
  参考文献：
  名称：

  Thiosemicarbazones derived from 1-indanones as new anti-Trypanosoma cruzi agents

  摘要：

  In the present work, we synthesized a series of thiosemicarbazones derived from 1-indanones with good anti-Trypanosoma cruzi activity. Most of them displayed remarkable trypanosomicidal activity. All the compounds showed nonspecific cytotoxicity on human erythrocytes. The ability of the new compounds to inhibit cruzipain, the major cysteine protease of T. cruzi, was also explored. Thiosemicarbazones 12 and 24 inhibited this enzyme at the dose assayed. This interaction was also studied in terms of molecular docking. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.037