7-甲基-5-硝基-1H-吲唑 | 75785-12-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 中文名称: 7-甲基-5-硝基-1H-吲唑
• 中文别名: 5-硝基-7-甲基-1H吲唑
• 英文名称: 7-Methyl-5-nitro-1H-indazol
• 英文别名: 7-methyl-5-nitro-1H-indazole
• CAS: 75785-12-5
• 化学式: C₈H₇N₃O₂
• mdl: MFCD03792677
• 分子量: 177.162
• InChiKey: JOJIHKJWRAFXSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  74.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-甲基-5-硝基-1H-吲唑 在 potassium carbonate 、 三乙胺 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 14.0h， 生成
  参考文献：
  名称：

  铑催化的使用N-酰胺基团的吲哚的区域选择性C7-精制

  摘要：

  描述了吲哚的铑催化的区域选择性CH烯化反应。该方案依赖于使用高效，可去除的N，N-二异丙基氨基甲酰基导向基团，该基团可轻松获得具有高区域选择性，充足的底物范围和宽泛的官能团耐受性的C7烯烃基吲唑。

  DOI：

  10.1002/asia.201601456
• 作为产物：
  描述：

  2-6-二甲基-4-硝基苯胺 在 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 12.17h， 以52%的产率得到7-甲基-5-硝基-1H-吲唑
  参考文献：
  名称：

  Development of 2, 4-diaminoquinazoline derivatives as potent PAK4 inhibitors by the core refinement strategy

  摘要：

  Upon analysis of the reported crystal structure of PAK4 inhibitor KY04031 (PAK4 IC50 = 0.790 mu M) in the active site of PAK4, we investigated the possibility of changing the triazine core of KY04031 to a quinazoline. Using KY04031 as a starting compound, a library of 2, 4-diaminoquinazoline derivatives were designed and synthesized. These compounds were evaluated for PAK4 inhibition, leading to the identification of compound 9d (PAK4 IC50 = 0.033 mu M). Compound 9d significantly induced the cell cycle in the G1/S phase and inhibited migration and invasion of A549 cells that over-express PAK4 via regulation of the PAK4-LIMK1 signalling pathway. A docking study of compound 9d was performed to elucidate its possible binding modes and to provide a structural basis for further structure-guided design of PAK4 inhibitors. Compound 9d may serve as a lead compound for anticancer drug discovery and as a valuable research probe for further biological investigation of PAK4. (C) 2017 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2017.02.063

文献信息

• Ruechardt, Christoph; Hassmann, Volker, Liebigs Annalen der Chemie, 1980, # 6, p. 908 - 927
  作者：Ruechardt, Christoph、Hassmann, Volker

  DOI：——

  日期：——
• WO2021007477A5
  申请人：——

  公开号：WO2021007477A5

  公开（公告）日：2023-07-19
• Brotzeller, Uwe; Nyitrai, Jozsef; Musso, Hans, Chemische Berichte, 1980, vol. 113, # 11, p. 3610 - 3620
  作者：Brotzeller, Uwe、Nyitrai, Jozsef、Musso, Hans

  DOI：——

  日期：——
• Buchwald reaction as the key step for the synthesis of metabolically more stable analogs of amodiaquine
  作者：Nicolas Le Fur、Guillaume Hochart、Paul-Emmanuel Larchanché、Patricia Melnyk

  DOI：10.1016/j.ejmech.2011.04.047

  日期：2011.7

  Amodiaquine is one of the most active anti-malarial 4-aminoquinoline but its metabolization is believed to generate hepatotoxic derivatives. Previously, we described new analogs of amodiaquine and amopyroquine, in which hydroxyl group was replaced by various amino groups and identified highly potent compounds with lower toxicity. We describe here the synthesis of new analogs that have been modified on their 4'- and 5'-positions in order to reduce their metabolization. A new synthetic strategy was developed using Buchwald coupling reaction as the key step. (C) 2011 Elsevier Masson SAS. All rights reserved.
• RUECHARDT C.; HASSMANN V., LIEBIGS ANN. CHEM., 1980, NO 6, 908-927
  作者：RUECHARDT C.、 HASSMANN V.

  DOI：——

  日期：——