N-[5-(3-hydroxy-5-nitro-1H-indazol-1-yl)-3-oxapentyl]thiomorpholine | 1042083-08-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 英文名称: N-[5-(3-hydroxy-5-nitro-1H-indazol-1-yl)-3-oxapentyl]thiomorpholine
• 英文别名: 5-nitro-1-[2-(2-thiomorpholin-4-ylethoxy)ethyl]-2H-indazol-3-one
• CAS: 1042083-08-8
• 化学式: C₁₅H₂₀N₄O₄S
• 分子量: 352.414
• InChiKey: AXEKPFYIFSJVLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  硫代吗啉 、 5-(3-hydroxy-5-nitro-1H-indazol-1-yl)-3-oxapentyl bromide 以 乙腈 为溶剂， 反应 32.0h， 以95%的产率得到N-[5-(3-hydroxy-5-nitro-1H-indazol-1-yl)-3-oxapentyl]thiomorpholine
  参考文献：
  名称：

  Study of 5-nitroindazoles' anti-Trypanosoma cruzi mode of action: Electrochemical behaviour and ESR spectroscopic studies

  摘要：

  New indazole derivatives have been developed to know about structural requirements for adequate anti-Trypanosoma cruzi activity. In relation to position 1 of indazole ring, we have observed that a butylaminopentyl substituent (14) affords good activity, but N-oxidation of omega-tertiary amino moiety yields completely inactive compounds (17,18); the substituent at position 3 of indazole ring affects drastically the in vitro activity, 3-OH derivative 13 being completely inactive. On the other hand, since compound 22, denitro-analogue of active compound 4, does not show activity, the 5-nitro substituent of indazole ring seems to be essential. Intramolecular cyclization of side chain at position 1 also affords inactive compounds (19, 20). The electrochemical studies showed that the trypanocidal 5-nitroindazole derivatives yielded nitro-anion radical via one-electron process at physiological pH. This electrochemical behaviour occurs in the parasite according to ESR experiment with the T cruzi microsomal fraction showing that 5-nitroindazole derivatives suffer bio-reduction without reactive oxygen species generation. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.07.018

文献信息

• Study of 5-nitroindazoles' anti-Trypanosoma cruzi mode of action: Electrochemical behaviour and ESR spectroscopic studies
  作者：Jorge Rodríguez、Alejandra Gerpe、Gabriela Aguirre、Ulrike Kemmerling、Oscar E. Piro、Vicente J. Arán、Juan Diego Maya、Claudio Olea-Azar、Mercedes González、Hugo Cerecetto

  DOI：10.1016/j.ejmech.2008.07.018

  日期：2009.4

  New indazole derivatives have been developed to know about structural requirements for adequate anti-Trypanosoma cruzi activity. In relation to position 1 of indazole ring, we have observed that a butylaminopentyl substituent (14) affords good activity, but N-oxidation of omega-tertiary amino moiety yields completely inactive compounds (17,18); the substituent at position 3 of indazole ring affects drastically the in vitro activity, 3-OH derivative 13 being completely inactive. On the other hand, since compound 22, denitro-analogue of active compound 4, does not show activity, the 5-nitro substituent of indazole ring seems to be essential. Intramolecular cyclization of side chain at position 1 also affords inactive compounds (19, 20). The electrochemical studies showed that the trypanocidal 5-nitroindazole derivatives yielded nitro-anion radical via one-electron process at physiological pH. This electrochemical behaviour occurs in the parasite according to ESR experiment with the T cruzi microsomal fraction showing that 5-nitroindazole derivatives suffer bio-reduction without reactive oxygen species generation. (C) 2008 Elsevier Masson SAS. All rights reserved.