2-allyl-6-nitro-2H-indazole | 501918-63-4

• 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-6-nitro-2H-indazole
• 英文别名: 6-Nitro-2-prop-2-enylindazole
• CAS: 501918-63-4
• 化学式: C₁₀H₉N₃O₂
• 分子量: 203.2
• InChiKey: XZQOXZJSGMRTPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 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：

  2-allyl-6-nitro-2H-indazole 、 2,5-己二酮 在 溶剂黄146 、 tin(ll) chloride 作用下， 以 四氢呋喃 为溶剂， 以78%的产率得到2-allyl-6-(2,5-dimethyl-pyrrol-1-yl)-2H-indazole
  参考文献：
  名称：

  One-pot synthesis of new 6-pyrrolyl- N -alkyl-indazoles from reductive coupling of N -alkyl-6-nitroindazoles and 2,5-hexadione

  摘要：

  One-pot synthesis of 6-pyrrolyl-N-alkyl-indazoles by the reductive coupling of N-alkyl-6-nitroindazoles and 2,5-hexadione was investigated in the presence of different reducing agents (SnCl2/AcOH and In/AcOH in THF). Indazoles 5a-h and 6a-h were obtained in good to excellent yields (74-95%) and characterized by elemental analysis, NMR, and single crystal X-ray diffraction. The same synthetic approach was also used to obtain 5-pyrrolyl-N-alkyl-indazoles. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.11.071
• 作为产物：
  描述：

  3-溴丙烯 、 6-硝基吲唑 在 氢化镓 、 氢化铝 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 以50%的产率得到2-allyl-6-nitro-2H-indazole
  参考文献：
  名称：

  Regioselective synthesis of 2H-indazoles through Ga/Al- and Al-mediated direct alkylation reactions of indazoles

  摘要：

  已开发出一种用于选择性合成2H-吲唑的高产率程序。

  DOI：

  10.1039/c5ob01747e

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
• Synthesis and biological evaluation against <i>Leishmania donovani</i> of novel hybrid molecules containing indazole-based 2-pyrone scaffolds
  作者：M. El Ghozlani、L. Bouissane、M. Berkani、S. Mojahidi、A. Allam、C. Menendez、S. Cojean、P. M. Loiseau、M. Baltas、E. M. Rakib

  DOI：10.1039/c8md00475g

  日期：——

  A series of novel indazole–pyrone hybrids are synthesized and tested in vitro against both Leishmania donovani axenic and intramacrophage amastigotes.

  合成了一系列新型吲唑-吡喃酮杂交化合物，并对其进行了针对唐氏利什曼原虫轴突和滋养体内变形虫的体外测试。
• Selective Synthesis of 1-Functionalized-alkyl-1<i>H</i>-indazoles
  作者：Kevin W. Hunt、David A. Moreno、Nicole Suiter、Christopher T. Clark、Ganghyeok Kim

  DOI：10.1021/ol902050m

  日期：2009.11.5

  An efficient method for the selective "N1" alkylation of indazoles is described. Use of alpha-halo esters, lactones, ketones, amides, and bromoacetonitrile provides good to excellent yield of the desired N1 products.
• 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.
• Regioselective synthesis of 2H-indazoles through Ga/Al- and Al-mediated direct alkylation reactions of indazoles
  作者：Mei-Huey Lin、Han-Jun Liu、Wei-Cheng Lin、Chung-Kai Kuo、Tsung-Hsun Chuang

  DOI：10.1039/c5ob01747e

  日期：——

  A procedure has been developed for the regioselective, high yielding synthesis of 2H-indazoles.

  已开发出一种用于选择性合成2H-吲唑的高产率程序。