2-ethyl-6-nitro-2H-indazole | 65642-29-7

• 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-ethyl-6-nitro-2H-indazole
• 英文别名: 2H-Indazole, 2-ethyl-6-nitro-；2-ethyl-6-nitroindazole
• CAS: 65642-29-7
• 化学式: C₉H₉N₃O₂
• 分子量: 191.189
• InChiKey: JPZZMLKQTUBUOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 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-ethyl-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75%的产率得到6-(2,5-dimethyl-pyrrol-1-yl)-2-ethyl-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：

  triethyloxonium fluoroborate 、 6-硝基吲唑 以 二氯甲烷 为溶剂， 反应 16.0h， 以50%的产率得到2-ethyl-6-nitro-2H-indazole
  参考文献：
  名称：

  Efficient and Regioselective Synthesis of 2-Alkyl-2H-indazoles

  摘要：

  An efficient and regioselective synthesis of 2-methyl-2H-indazoles and 2-ethyl-2H-indazoles using trimethyloxonium tetrafluoroborate or triethyloxonium hexafluorophosphate is reported.

  DOI：

  10.1021/jo0265434

文献信息

• 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。
• On the reactions of tertiary carbanions with some nitroindazoles and nitrobenzotriazoles
  作者：Marek K. Bernard、Jacek Kujawski、Urszula Skierska、Andrzej K. Gzella、Wojciech Jankowski

  DOI：10.3998/ark.5550190.0013.816

  日期：——

  The vicarious nucleophilic substitution in some nit roindazole and nitrobenzotriazole derivatives with tertiary carbanions leads almost exclusively t o products substituted para to the nitro group. As results from the theoretical calculations and st ructural evidences, such reaction outcome is due mainly to the stereoelectronic reasons in combi nation with the considerable shortening of the Cortho

  某些硝基罗吲唑和硝基苯并三唑衍生物中的替代亲核取代与叔碳负离子几乎完全导致产物在硝基的对位被取代。从理论计算和结构证据来看，这种反应结果主要是由于立体电子学的原因和Cortho-CNO 2 键的显着缩短相结合。手性和前手性中心（分别为次甲基和 N 亚甲基基团）的存在通常会引起亚甲基质子信号的额外分裂，该信号在长距离上传输，前提是偶联途径中没有吡啶氮。
• Selective N2-Alkylation of 1H-Indazoles and 1H-Azaindazoles
  作者：Allyn T. Londregan、Jennifer Clemens、Emily L. Bell

  DOI：10.1055/s-0040-1719917

  日期：2022.7

  A general and selective procedure for the N2-alkylation of 1H-indazoles and 1H-azaindazoles is presented. Promoted by either trifluoromethanesulfonic acid or copper(II) triflate, diverse 1H-indazoles/azaindazoles are selectively alkylated with varied primary, secondary, and tertiary alkyl 2,2,2-trichloroacetimidates at the N2-nitrogen to afford the corresponding 2-alkyl-2H-indazoles/azaindazoles. Forty-one

  介绍了 1 H-吲唑和 1 H-氮杂吲唑的 N2-烷基化的一般和选择性程序。在三氟甲磺酸或三氟甲磺酸铜 (II) 的促进下，不同的 1 H-吲唑/氮杂吲唑在 N2-氮上被不同的伯、仲和叔烷基 2,2,2-三氯乙酰亚胺酯选择性烷基化，得到相应的 2-烷基-2 H-吲唑/氮杂吲唑。包括四十一个例子以及对反应优化、范围和机理的讨论。
• Design of Promising Thiazoloindazole-Based Acetylcholinesterase Inhibitors Guided by Molecular Docking and Experimental Insights
  作者：Fatima Ezzahra Laghchioua、Carlos F. M. da Silva、Diana C. G. A. Pinto、José A. S. Cavaleiro、Ricardo F. Mendes、Filipe A. Almeida Paz、Maria A. F. Faustino、El Mostapha Rakib、M. Graça P. M. S. Neves、Florbela Pereira、Nuno M. M. Moura

  DOI：10.1021/acschemneuro.4c00241

  日期：2024.8.7

  donepezil, a well-known AChE inhibitor used in Alzheimer’s disease treatment. Sustained by these findings, two series of compounds were synthesized. One series included a triazole moiety (Tl45a–c), while the other incorporated a carbazole moiety (Tl58a–c). These compounds were isolated in yields ranging from 66 to 87% through nucleophilic substitution and Cu(I)-catalyzed azide–alkyne 1,3-dipolar cycloaddition

  阿尔茨海默病的特点是认知功能进行性恶化和记忆丧失，与胆碱能神经传递失调密切相关。由于乙酰胆碱酯酶（AChE）是神经系统中的一种关键酶，负责分解神经递质乙酰胆碱，因此其抑制在各种神经系统疾病的治疗中具有重要意义。因此，开发能够提高乙酰胆碱水平、最终改善胆碱能神经传递的有效 AChE 抑制剂至关重要。本文报告的结果代表了新型噻唑并吲唑基化合物的开发向前迈出了一步，这些化合物有潜力作为有效的乙酰胆碱酯酶抑制剂。分子对接研究表明，某些经过评估的硝基吲唑类化合物的性能优于多奈哌齐（多奈哌齐），多奈哌齐是一种用于治疗阿尔茨海默氏病的著名乙酰胆碱酯酶抑制剂。根据这些发现，合成了两个系列的化合物。一个系列包含三唑部分 ( Tl45a–c )，而另一个系列包含咔唑部分 ( Tl58a–c )。通过亲核取代和 Cu(I) 催化的叠氮化物-炔烃 1,3-偶极环加成 (CuAAC) 反应分离出这些化合物，收率范围为
• An expedient, regioselective synthesis of novel 2-alkylamino- and 2-alkylthiothiazolo[5,4-e]- and -[4,5-g]indazoles and their anticancer potential
  作者：Manas Chakrabarty、Taraknath Kundu、Shiho Arima、Yoshihiro Harigaya

  DOI：10.1016/j.tet.2008.05.009

  日期：2008.7

  Several novel 2-alkylamino- and 2-alkylthiothiazolo[5,4-e]- and -[4,5-g]indazoles and their 6-alkyl and 8-alkyl derivatives have been synthesised in high overall yields starting from 5-nitro and 6-nitro-indazoles in a three-step route involving the regioselective cyclisation of thioureidoindazoles and indazolyl dithiocarbamates as the key steps. Some assorted thiazoloindazoles have been screened for anticancer properties, which demonstrated the anticancer potential of at least one product, justifying its further follow-up. (C) 2008 Elsevier Ltd. All rights reserved.