N-[2-(1H-indol-3-yl)ethyl]-3-methoxybenzamide | 339165-45-6

• 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
• 英文名称: N-[2-(1H-indol-3-yl)ethyl]-3-methoxybenzamide
• CAS: 339165-45-6
• 化学式: C₁₈H₁₈N₂O₂
• 分子量: 294.353
• InChiKey: INOUBWOFBVLRCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  54.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-[2-(1H-indol-3-yl)ethyl]-3-methoxybenzamide 在 三氯氧磷 作用下， 生成 1-(3-methoxyphenyl)-4,9-dihydro-3H-pyrido[3,4-b]indole
  参考文献：
  名称：

  M4 agonists/5HT7 antagonists with potential as antischizophrenic drugs: Serominic compounds

  摘要：

  Chronic low-dose treatment of rats with the psychomimetic drug, phencyclidine, induces regionally specific metabolic and neurochemical changes in the CNS that mirror those observed in the brains of schizophrenic patients. Recent evidence suggests that drugs targeting serotoninergic and muscarinic receptors, and in particular 5-HT7 antagonists and M-4 agonists, exert beneficial effects in this model of schizophrenia. Compounds that display this combined pattern of activity we refer to as serominic compounds. Based upon leads from natural product screening, we have designed and synthesised such serominic compounds, which are principally arylamidine derivatives of tetrahydroisoquinolines, and shown that they have the required serominic profile in ligand binding assays and show potential antipsychotic activity in functional assays. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.093
• 作为产物：
  描述：

  色胺 、 间甲氧基苯甲酰氯 生成 N-[2-(1H-indol-3-yl)ethyl]-3-methoxybenzamide
  参考文献：
  名称：

  M4 agonists/5HT7 antagonists with potential as antischizophrenic drugs: Serominic compounds

  摘要：

  Chronic low-dose treatment of rats with the psychomimetic drug, phencyclidine, induces regionally specific metabolic and neurochemical changes in the CNS that mirror those observed in the brains of schizophrenic patients. Recent evidence suggests that drugs targeting serotoninergic and muscarinic receptors, and in particular 5-HT7 antagonists and M-4 agonists, exert beneficial effects in this model of schizophrenia. Compounds that display this combined pattern of activity we refer to as serominic compounds. Based upon leads from natural product screening, we have designed and synthesised such serominic compounds, which are principally arylamidine derivatives of tetrahydroisoquinolines, and shown that they have the required serominic profile in ligand binding assays and show potential antipsychotic activity in functional assays. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.093

文献信息

• First reported propylphosphonic anhydride (T3P®) mediated Robinson–Gabriel cyclization. Synthesis of natural and unnatural 5-(3-indolyl)oxazoles
  作者：Tímea Szabó、András Dancsó、Péter Ábrányi-Balogh、Balázs Volk、Mátyás Milen

  DOI：10.1016/j.tetlet.2019.04.024

  日期：2019.5

  In the present work, a propylphosphonic anhydride (T3P®) assisted Robinson–Gabriel cyclization of N-acyl-β-oxotryptamines for the synthesis of 2-substituted-5-(3-indolyl)oxazoles has been developed. The reactions proceeded smoothly in acetonitrile under microwave irradiation, and the product isolation required only an extraction and subsequent crystallization; no chromatography was necessary. The desired

  在目前的工作中，丙基膦酸酐（T3P ®）辅助的罗宾逊-加布里埃尔环化Ñ酰基-β-oxotryptamines为2-取代-5-（3-吲哚基）恶唑已经开发的合成。在微波辐射下，反应在乙腈中顺利进行，产物的分离仅需萃取并随后结晶。无需层析。以良好至优异的产率获得了所需的产物。