2-allyl-4-nitro-2H-indazole | 1310822-30-0

• 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: 2-allyl-4-nitro-2H-indazole
• 英文别名: 4-Nitro-2-prop-2-enylindazole；4-nitro-2-prop-2-enylindazole
• CAS: 1310822-30-0
• 化学式: C₁₀H₉N₃O₂
• 分子量: 203.2
• InChiKey: PHYGSROOUVWGFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙醇 、 2-allyl-4-nitro-2H-indazole 、 对甲苯磺酰氯 在 tin(ll) chloride 、 吡啶 作用下， 反应 24.0h， 以53%的产率得到N-(2-allyl-7-ethoxy-2H-indazol-4-yl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Alkylation and Reduction of N-Alkyl-4-nitroindazoles with Anhydrous SnCl2 in Ethanol: Synthesis of Novel 7-Ethoxy-N-alkylindazole Derivatives

  摘要：

  New series of indazoles substituted at the N-1 and N-2 positions and their 7-ethoxy derivatives have been synthesis starting from alkylation of 4-nitroindazole and reduction of alkyl-nitro-derivatives with anhydrous SnCl2 in ethanol. The structures of the products obtained were characterized using H-1 NMR, C-13 NMR, MS spectrometry and elemental analysis; the NMR spectroscopic data were used for structural assignment of the N-1 and N-2 isomers.

  DOI：

  10.3987/com-11-12149
• 作为产物：
  描述：

  2-甲基-3-硝基苯胺 在 potassium hydroxide 、 sodium nitrite 作用下， 以 水 、 溶剂黄146 、 丙酮 为溶剂， 反应 0.25h， 生成 2-allyl-4-nitro-2H-indazole
  参考文献：
  名称：

  Alkylation and Reduction of N-Alkyl-4-nitroindazoles with Anhydrous SnCl2 in Ethanol: Synthesis of Novel 7-Ethoxy-N-alkylindazole Derivatives

  摘要：

  New series of indazoles substituted at the N-1 and N-2 positions and their 7-ethoxy derivatives have been synthesis starting from alkylation of 4-nitroindazole and reduction of alkyl-nitro-derivatives with anhydrous SnCl2 in ethanol. The structures of the products obtained were characterized using H-1 NMR, C-13 NMR, MS spectrometry and elemental analysis; the NMR spectroscopic data were used for structural assignment of the N-1 and N-2 isomers.

  DOI：

  10.3987/com-11-12149

文献信息

• Synthesis, antiproliferative and apoptotic activities of N-(6(4)-indazolyl)-benzenesulfonamide derivatives as potential anticancer agents
  作者：Najat Abbassi、Hakima Chicha、El Mostapha Rakib、Abdellah Hannioui、Mdaghri Alaoui、Abdelouahed Hajjaji、Detlef Geffken、Cinzia Aiello、Rosaria Gangemi、Camillo Rosano、Maurizio Viale

  DOI：10.1016/j.ejmech.2012.09.013

  日期：2012.11

  possess many types of biological activities, including anticancer activity. The present work reports the synthesis and antiproliferative evaluation of some N-(6(4)-indazolyl)benzenesulfonamides and 7-ethoxy-N-(6(4)-indazolyl)benzenesulfonamides. All compounds were evaluated for their in vitro antiproliferative activity against three tumor cell lines: A2780 (human ovarian carcinoma) A549 (human lung

  最近，已经报道带有磺酰胺部分的化合物具有许多类型的生物学活性，包括抗癌活性。本工作报告了一些N-（6（4）-吲唑基）苯磺酰胺和7-乙氧基-N-（6（4）-吲唑基）苯磺酰胺的合成和抗增殖评价。 评估了所有化合物对三种肿瘤细胞系的体外抗增殖活性：A2780（人类卵巢癌），A549（人类肺腺癌）和P388（鼠白血病）。结果表明，磺酰胺2C，3C，6D，8，13，3B和16被赋予与化合物的药理学上感兴趣的抗增殖活性2C和3C示出了下IC 50（分别从0.50±0.09至1.83±0.52μM和从0.58±0.17至5.83±1.83μM）。此外，这些吲唑能够通过上调典型的凋亡标记p53和bax来触发凋亡。 由于考虑到这些化合物的假设的目标，一个初步对接分析表明，所有的化合物似乎与β微管蛋白相互作用，特别是化合物3b中的是显示出低ķ我。细胞周期阶段的细胞荧光分析表明，所有化合物以其IC 75给药时，都会导致细胞周期的G2
• Alkylation and Reduction of N-Alkyl-4-nitroindazoles with Anhydrous SnCl2 in Ethanol: Synthesis of Novel 7-Ethoxy-N-alkylindazole Derivatives
  作者：El Mostapha Rakib、Najat Abbassi、Abdellah Hannioui、Mdaghri Alaoui、Mohamed Benchidmi、El Mokhtar Essassi、Detlef Geffken

  DOI：10.3987/com-11-12149

  日期：——

  New series of indazoles substituted at the N-1 and N-2 positions and their 7-ethoxy derivatives have been synthesis starting from alkylation of 4-nitroindazole and reduction of alkyl-nitro-derivatives with anhydrous SnCl2 in ethanol. The structures of the products obtained were characterized using H-1 NMR, C-13 NMR, MS spectrometry and elemental analysis; the NMR spectroscopic data were used for structural assignment of the N-1 and N-2 isomers.