7-甲氧基-1H-吲唑-3-羧酸乙酯 | 885278-98-8

• 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-甲氧基-1H-吲唑-3-羧酸乙酯
• 中文别名: 7-甲氧基-1H-吲唑-3羧酸乙酯
• 英文名称: 3-ethoxycarbonyl-7-methoxy-1H-indazole
• 英文别名: ethyl 7-methoxy-1H-indazole-3-carboxylate；ethyl 7-methoxy-2H-indazole-3-carboxylate
• CAS: 885278-98-8
• 化学式: C₁₁H₁₂N₂O₃
• 分子量: 220.228
• InChiKey: ZFBHKJGLDLREGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  64.2
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  7-甲氧基-1H-吲唑-3-羧酸乙酯 在 盐酸 、 甲醇 、 potassium tert-butylate 、 三溴化硼 、 四丁基碘化铵 、 potassium carbonate 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 7-(2-(2-(2-(7-(diethylamino)-2-oxo-2H-chromene-3-carboxamido)ethoxy)ethoxy)ethoxy)-1-methyl-N-(9-methyl-9-azabicyclo[3.3.1]nonan-3-yl)-1H-indazole-3-carboxamide
  参考文献：
  名称：

  High-affinity fluorescent ligands for the 5-HT3 receptor

  摘要：

  The synthesis, photophysical and biological characterization of a small library of fluorescent 5-HT3 receptor ligands is described. Several of these novel granisetron conjugates have high quantum yields and show high affinity for the human 5-HT(3)AR. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.097
• 作为产物：
  描述：

  ethyl 7-methoxy-2-{[(2-trimethylsilyl)ethoxy]methyl}-2H-indazole-3-carboxylate 在 盐酸 、 水 、 sodium carbonate 作用下， 以 乙醇 、 水 为溶剂， 以98%的产率得到7-甲氧基-1H-吲唑-3-羧酸乙酯
  参考文献：
  名称：

  Toward Biophysical Probes for the 5-HT₃ Receptor: Structure−Activity Relationship Study of Granisetron Derivatives

  摘要：

  This report describes the synthesis and biological characterization of novel granisetron derivatives that are antagonists of the human serotonin (5-HT(3)A) receptor. Some of these substituted granisetron derivatives showed low nanomolar binding affinity and allowed the identification of positions on the granisetron core that might be used as attachment points for biophysical tags. A BODIPY fluorophore was appended to one Such position and specifically bound to 5-HT(3)A receptors in mammalian cells.

  DOI：

  10.1021/jm901827x

文献信息

• Facile and efficient synthesis of indazole derivatives by 1,3-cycloaddition of arynes with diazo compounds and azomethine imides
  作者：Tienan Jin、Fan Yang、Yoshinori Yamamoto

  DOI：10.1135/cccc2009014

  日期：——

  N-Unsubstituted indazoles 3 and 1-arylindazoles 4 are readily available in good to high yields through [3+2] cycloaddition of 2-(trimethylsilyl)aryl triflates 1 and diazo compounds in the presence of KF or CsF under mild reaction conditions. Furthermore, we found that azomethine imides also underwent cycloaddition reaction with 2-(trimethylsilyl)phenyl triflates (1a) in the presence of KF to afford indazolone derivatives 6 in moderate yields.

  N-未取代吲唑3和1-芳基吲唑4可通过2-(三甲基硅基)芳基三氟甲烷磺酸酯1和重氮化合物在KF或CsF存在下在温和反应条件下进行[3+2]环加成反应，以良好至高产率方便获得。此外，我们发现偶氮亚甲基亚胺也可在KF存在下与2-(三甲基硅基)苯基三氟甲烷磺酸酯（1a）发生环加成反应，得到吲唑酮衍生物6，产率中等。
• Synthesis of Indazoles by the [3+2] Cycloaddition of Diazo Compounds with Arynes and Subsequent Acyl Migration
  作者：Zhijian Liu、Feng Shi、Pablo D. G. Martinez、Cristiano Raminelli、Richard C. Larock

  DOI：10.1021/jo702062n

  日期：2008.1.1

  The [3+2] cycloaddition of a variety of diazo compounds with o-(trimethylsilyl)aryl triflates in the presence of CsF or TBAF at room temperature provides a very direct, efficient approach to a wide range of potentially biologically and pharmaceutically interesting substituted indazoles in good to excellent yields under mild reaction conditions. Simple diazomethane derivatives afford N-unsubstituted

  在室温下，在CsF或TBAF存在下，各种重氮化合物与邻-（三甲基甲硅烷基）芳基三氟甲酸酯的[3 + 2]环加成反应，提供了一种直接，有效的方法，可用于处理许多潜在的生物学和药学上令人关注的取代的吲唑在温和的反应条件下，收率好至极好。简单的重氮甲烷衍生物根据试剂的化学计量和反应条件而提供N-未取代的吲唑或1-芳基化的吲唑，而含二羰基的重氮化合物进行羰基迁移以选择性地提供1-酰基或1-烷氧基羰基的吲唑。
• An Efficient, Facile, and General Synthesis of 1H-Indazoles by 1,3-Dipolar Cycloaddition of Arynes with Diazomethane Derivatives
  作者：Tienan Jin、Yoshinori Yamamoto

  DOI：10.1002/anie.200700101

  日期：2007.4.27
• High-affinity fluorescent ligands for the 5-HT3 receptor
  作者：Jonathan Simonin、Sanjeev Kumar V. Vernekar、Andrew J. Thompson、J. Daniel Hothersall、Christopher N. Connolly、Sarah C.R. Lummis、Martin Lochner

  DOI：10.1016/j.bmcl.2011.11.097

  日期：2012.1

  The synthesis, photophysical and biological characterization of a small library of fluorescent 5-HT3 receptor ligands is described. Several of these novel granisetron conjugates have high quantum yields and show high affinity for the human 5-HT(3)AR. (C) 2011 Elsevier Ltd. All rights reserved.
• Toward Biophysical Probes for the 5-HT₃ Receptor: Structure−Activity Relationship Study of Granisetron Derivatives
  作者：Sanjeev Kumar V. Vernekar、Hasan Y. Hallaq、Guy Clarkson、Andrew J. Thompson、Linda Silvestri、Sarah C. R. Lummis、Martin Lochner

  DOI：10.1021/jm901827x

  日期：2010.3.11

  This report describes the synthesis and biological characterization of novel granisetron derivatives that are antagonists of the human serotonin (5-HT(3)A) receptor. Some of these substituted granisetron derivatives showed low nanomolar binding affinity and allowed the identification of positions on the granisetron core that might be used as attachment points for biophysical tags. A BODIPY fluorophore was appended to one Such position and specifically bound to 5-HT(3)A receptors in mammalian cells.