5-nitro-3-methoxy-1-(2-morpholinoethyl)-1H-indazole | 1178949-23-9

• 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: 5-nitro-3-methoxy-1-(2-morpholinoethyl)-1H-indazole
• 英文别名: 3-methoxy-1-(2-morpholinoethyl)-5-nitro-1H-indazole；4-[2-(3-Methoxy-5-nitroindazol-1-yl)ethyl]morpholine
• CAS: 1178949-23-9
• 化学式: C₁₄H₁₈N₄O₄
• 分子量: 306.321
• InChiKey: MBEVHAFKFYXBSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  85.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-(2-氯乙基)吗啉盐酸盐 、 3-methoxy-5-nitro-1H-indazole 在 potassium carbonate 作用下， 以 丁酮 为溶剂， 反应 24.0h， 以79%的产率得到5-nitro-3-methoxy-1-(2-morpholinoethyl)-1H-indazole
  参考文献：
  名称：

  New potent 5-nitroindazole derivatives as inhibitors of Trypanosoma cruzi growth: Synthesis, biological evaluation, and mechanism of action studies

  摘要：

  New 5-nitroindazole derivatives were developed and their antichagasic properties studied. Eight compounds (14-18, 20, 26 and 28) displayed remarkable in vitro activities against Trypanosoma cruzi (T. cruzi). Its unspecific cytotoxicity against macrophages was evaluated being not toxic at a concentration at least twice that of T. cruzi IC50, for some derivatives. The electrochemical studies, parasite respiration studies and ESR experiment showed that 5-nitroindazole derivatives not be able to yield a redox cycling with molecular oxygen such as occurs with nifurtimox (Nfx). The study on the mechanism of action proves to be related to the production of reduced species of the nitro moiety similar to that observed with benznidazole. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.10.030

文献信息

• New potent 5-nitroindazole derivatives as inhibitors of Trypanosoma cruzi growth: Synthesis, biological evaluation, and mechanism of action studies
  作者：Jorge Rodríguez、Vicente J. Arán、Lucía Boiani、Claudio Olea-Azar、María Laura Lavaggi、Mercedes González、Hugo Cerecetto、Juan Diego Maya、Catalina Carrasco-Pozo、Hernán Speisky Cosoy

  DOI：10.1016/j.bmc.2009.10.030

  日期：2009.12.15

  New 5-nitroindazole derivatives were developed and their antichagasic properties studied. Eight compounds (14-18, 20, 26 and 28) displayed remarkable in vitro activities against Trypanosoma cruzi (T. cruzi). Its unspecific cytotoxicity against macrophages was evaluated being not toxic at a concentration at least twice that of T. cruzi IC50, for some derivatives. The electrochemical studies, parasite respiration studies and ESR experiment showed that 5-nitroindazole derivatives not be able to yield a redox cycling with molecular oxygen such as occurs with nifurtimox (Nfx). The study on the mechanism of action proves to be related to the production of reduced species of the nitro moiety similar to that observed with benznidazole. (C) 2009 Elsevier Ltd. All rights reserved.