1-methyl-3-(2-nitro-1-phenylethyl)-2-phenyl-1H-indole | 1148109-14-1

• 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: 1-methyl-3-(2-nitro-1-phenylethyl)-2-phenyl-1H-indole
• 英文别名: 1-Methyl-3-(2-nitro-1-phenylethyl)-2-phenylindole
• CAS: 1148109-14-1
• 化学式: C₂₃H₂₀N₂O₂
• 分子量: 356.424
• InChiKey: OFTOXEBAWTUTNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  50.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-methyl-3-(2-nitro-1-phenylethyl)-2-phenyl-1H-indole 在 三氯氧磷 、 三乙胺 作用下， 以 苯 为溶剂， 反应 0.58h， 以28%的产率得到2-(1-methyl-3-oxo-2-phenylindolin-2-yl)-2-phenylacetonitrile
  参考文献：
  名称：

  3-(2-硝基乙基)-1H-吲哚直接转化为2-(1H-吲哚-2-基)乙腈

  摘要：

  最近发现的硝基烯烃的[4+1]-螺环化反应生成吲哚，为制备2-( 1H-吲哚-2-基)乙腈提供了一种方便的新方法。然而，由于惰性3-(2-硝基乙基) -1H-吲哚副产物的形成，该反应变得复杂。在此，我们提供了解决此问题的方法，可以将不需要的副产物有效转化为乙腈目标分子。

  DOI：

  10.3390/molecules26206132
• 作为产物：
  描述：

  1-甲基-2-苯基吲哚 、 β-硝基苯乙烯 以 甘油 为溶剂， 反应 24.0h， 以62%的产率得到1-methyl-3-(2-nitro-1-phenylethyl)-2-phenyl-1H-indole
  参考文献：
  名称：

  甘油作为有机反应的有效促进介质

  摘要：

  尽管水对反应速率的有利影响随着反应物疏水性的增加而降低，但我们在此报告，使用甘油作为溶剂能够显着加快有机反应的反应速率，即使是从比疏水底物更多的疏水性底物开始通常在水上使用的那些。此外，在经济和环境上直接使用由生物柴油工业产生的粗制甘油的可能性提高了使用甘油作为溶剂的兴趣。

  DOI：

  10.1002/adsc.200800328

文献信息

• [EN] CANNABINOID TYPE 1 RECEPTOR MODULATORS<br/>[FR] MODULATEURS DU RÉCEPTEUR CANNABINOÏDE DE TYPE 1
  申请人：UNIV TORONTO

  公开号：WO2016029310A1

  公开（公告）日：2016-03-03

  The present disclosure relates to indole derivatives of the formula (I) which are cannabinoid type 1 receptor modulators and which are useful in the treatment of diseases in which modulation of the receptor is beneficial; to processes for their preparation; to pharmaceutical compositions comprising them; and to methods of using them.

  本公开涉及公式（I）的吲哚衍生物，这些衍生物是大麻素类型1受体调节剂，对于治疗需要调节受体的疾病是有益的；涉及它们的制备方法；包含它们的药物组合物；以及使用它们的方法。
• Cannabinoid type 1 receptor modulators
  申请人：The Governing Council of the University of Toronto

  公开号：US10377711B2

  公开（公告）日：2019-08-13

  The present disclosure relates to indole derivatives of the formula (I) which are cannabinoid type 1 receptor modulators and which are useful in the treatment of diseases in which modulation of the receptor is beneficial; to processes for their preparation; to pharmaceutical compositions comprising them; and to methods of using them.

  本公开涉及式（I）的吲哚衍生物，它们是大麻素 1 型受体调节剂，可用于治疗对调节受体有益的疾病；涉及它们的制备工艺；涉及包含它们的药物组合物；还涉及使用它们的方法。
• Identification of CB1 Receptor Allosteric Sites Using Force-Biased MMC Simulated Annealing and Validation by Structure–Activity Relationship Studies
  作者：Dow P. Hurst、Sumanta Garai、Pushkar M. Kulkarni、Peter C. Schaffer、Patricia H. Reggio、Ganesh A. Thakur

  DOI：10.1021/acsmedchemlett.9b00256

  日期：2019.8.8

  Positive allosteric modulation of the cannabinoid 1 receptor (CB1R) has demonstrated distinct therapeutic advantages that address several limitations associated with orthosteric agonism and has opened a promising therapeutic avenue for further drug development. To advance the development of CB1R positive allosteric modulators, it is important to understand the molecular architecture of CB1R allosteric site(s). The goal of this work was to use Force-Biased MMC Simulated Annealing to identify binding sites for GAT228 (R), a partial allosteric agonist, and GAT229 (S), a positive allosteric modulator (PAM) at the CB1R. Our studies suggest that GAT228 binds in an intracellular (IC) TMH1-2-4 exosite that would allow this compound to act as a CB1 allosteric agonist as well as a CB1 PAM. In contrast, GAT229 binds at the extracellular (EC) ends of TMH2/3, just beneath the EC1 loop. At this site, this compound can act as CB1 PAM only. Finally, these results were successfully validated through the synthesis and biochemical evaluation of a focused library of compounds.
• CANNABINOID TYPE 1 RECEPTOR MODULATORS
  申请人：The Governing Council of the University of Toronto

  公开号：US20180118681A1

  公开（公告）日：2018-05-03

  The present disclosure relates to indole derivatives of the formula (I) which are cannabinoid type 1 receptor modulators and which are useful in the treatment of diseases in which modulation of the receptor is beneficial; to processes for their preparation; to pharmaceutical compositions comprising them; and to methods of using them.