1-苯基-1H-吲哚-3-甲酸甲酯 | 244090-32-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 1-苯基-1H-吲哚-3-甲酸甲酯
• 英文名称: 1-phenylindole-3-carboxylic acid methyl ester
• 英文别名: methyl 1-phenyl-1H-indole-3-carboxylate；Methyl N-phenyl-3-indolecarboxylate；methyl 1-phenylindole-3-carboxylate
• CAS: 244090-32-2
• 化学式: C₁₆H₁₃NO₂
• 分子量: 251.285
• InChiKey: WVGAXYQYTMLRNQ-UHFFFAOYSA-N

物化性质

• 沸点：
  343.7±25.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-苯基-1H-吲哚-3-甲酸甲酯 在 氢氧化钾 、 水 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 1-苯基-1H-吲哚-3-羧酸
  参考文献：
  名称：

  Replacement of the quinoline system in 2-phenyl-4-quinolinecarboxamide NK-3 receptor antagonists

  摘要：

  Results from a medicinal chemistry approach aimed at replacing the quinoline ring system in the potent and selective human neurokinin-3 (hNK-3) receptor antagonists 1-4 of general formula I are discussed. The data give further insight upon the potential NK-3 pharmacophore. In particular, it is highlighted that both the benzene-condensed ring and the quinoline nitrogen are crucial determinants for optimal binding affinity to the hNK-3 receptor. Some novel compounds maintained part of the binding affinity to the receptor (5, 6, 10 and 13) and compound 5, featuring the naphthalene ring system, appears to be suitable for further modifications; it offers the option to introduce electron-withdrawing groups at position 2 and 4, conferring on the ring an overall electron-deficiency similar to that of the quinoline. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(99)00043-9
• 作为产物：
  描述：

  1-苯基-1H-吲哚 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 1-苯基-1H-吲哚-3-甲酸甲酯
  参考文献：
  名称：

  Replacement of the quinoline system in 2-phenyl-4-quinolinecarboxamide NK-3 receptor antagonists

  摘要：

  Results from a medicinal chemistry approach aimed at replacing the quinoline ring system in the potent and selective human neurokinin-3 (hNK-3) receptor antagonists 1-4 of general formula I are discussed. The data give further insight upon the potential NK-3 pharmacophore. In particular, it is highlighted that both the benzene-condensed ring and the quinoline nitrogen are crucial determinants for optimal binding affinity to the hNK-3 receptor. Some novel compounds maintained part of the binding affinity to the receptor (5, 6, 10 and 13) and compound 5, featuring the naphthalene ring system, appears to be suitable for further modifications; it offers the option to introduce electron-withdrawing groups at position 2 and 4, conferring on the ring an overall electron-deficiency similar to that of the quinoline. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(99)00043-9

文献信息

• [EN] OXADIAZOLE DERIVATIVES AND THEIR USE AS NICOTINIC ACETYLCHOLINE RECEPTOR MODULATORS<br/>[FR] DÉRIVÉS D'OXADIAZOLE ET LEUR UTILISATION COMME MODULATEURS DES RÉCEPTEURS NICOTINIQUES DE L'ACÉTYLCHOLINE
  申请人：GLAXO GROUP LTD

  公开号：WO2009071577A1

  公开（公告）日：2009-06-11

  Oxadiazole derivatives of formula (I) where ring A is a bicyclic or tricyclic system. Claimed compounds are active on nicotinic acetylcholine receptors (nAChRs), and are useful to treat neurological, psychiatric, and gastrointestinal disorders, as well as sepsis and obesity.

  Oxadiazole衍生物的化学式（I），其中环A是一个双环或三环系统。所述化合物对尼古丁型乙酰胆碱受体（nAChRs）具有活性，并可用于治疗神经系统、精神病学和胃肠道疾病，以及败血症和肥胖症。
• Selective copper catalysed aromatic N-arylation in water
  作者：Jens Engel-Andreasen、Bharat Shimpukade、Trond Ulven

  DOI：10.1039/c2gc36589h

  日期：——

  4,7-Dipyrrolidinyl-1,10-phenanthroline (DPPhen) was identified as an efficient ligand for copper catalysed selective aromatic N-arylation in water. N-Arylation of indoles, imidazoles and purines proceeds with moderate to excellent yields and complete selectivity over aliphatic amines. Aqueous medium and the possibility for low metal and ligand loadings give the process a benign environmental profile.

  4,7-二吡咯烷基-1,10-菲蒽 (DPPhen) 被确定为一种高效的配体，用于在水中催化选择性芳香族氮芳基化的铜催化反应。吲哚、咪唑及嘌呤的氮芳基化反应以中等到优良的产率进行，并对脂肪胺具有完全的选择性。水相介质和低金属及配体用量的可能性使该过程具有良好的环境特征。
• AMIDE COMPOUNDS
  申请人：Kitamura Shuji

  公开号：US20120065196A1

  公开（公告）日：2012-03-15

  The present invention provides compounds represented by the formula (Ie): and the formula (If): wherein each symbol is as defined in the specification. According to the present invention, these compounds have a DGAT inhibitory activity and are useful for the prophylaxis, treatment or improvement of diseases or pathologies caused by high expression or high activation of DGAT.

  本发明提供由式(Ie)和式(If)所表示的化合物，其中每个符号如规范中所定义。根据本发明，这些化合物具有DGAT抑制活性，并可用于预防、治疗或改善由DGAT高表达或高活化引起的疾病或病理学。
• 5-HT3 RECEPTOR ANTAGONISTS
  申请人：Takeda Pharmaceutical Company Limited

  公开号：US20160185801A1

  公开（公告）日：2016-06-30

  The present invention provides compounds of the formula: that are 5HT3 receptor antagonists and are therefore useful for the treatment of diseases treatable by inhibition of 5HT3 receptor such as emesis, pain, drug addiction, neurodegenerative and psychiatric disorders, and GI disorders. Also provided are pharmaceutical compositions containing such compounds and processes for preparing such compounds.

  本发明提供的化合物具有以下公式： 这些化合物是5HT3受体拮抗剂，因此可用于治疗可通过抑制5HT3受体治疗的疾病，例如呕吐、疼痛、药物成瘾、神经退行性和精神障碍以及胃肠道疾病。还提供了包含这些化合物的制药组合物和制备这些化合物的方法。
• 5-HT3 receptor antagonists
  申请人：Takeda Pharmaceutical Company Limited

  公开号：US09303045B2

  公开（公告）日：2016-04-05

  The present invention provides compounds of the formula: that are 5HT3 receptor antagonists and are therefore useful for the treatment of diseases treatable by inhibition of 5HT3 receptor such as emesis, pain, drug addiction, neurodegenerative and psychiatric disorders, and GI disorders. Also provided are pharmaceutical compositions containing such compounds and processes for preparing such compounds.

  本发明提供了以下式子的化合物：它们是5HT3受体拮抗剂，因此可用于治疗可通过抑制5HT3受体治疗的疾病，如恶心、疼痛、药物成瘾、神经退行性和精神障碍以及胃肠疾病。还提供了含有这种化合物的制药组合物和制备这种化合物的过程。