(2-indol-3-yl-ethyl)-naphthalen-2-ylmethylene-amine | 16783-86-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2-indol-3-yl-ethyl)-naphthalen-2-ylmethylene-amine
• 英文别名: N-(2-Naphthyl-methylen)-tryptamin
• CAS: 16783-86-1
• 化学式: C₂₁H₁₈N₂
• 分子量: 298.387
• InChiKey: CNRYARGFGBQYCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.98
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  28.15
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (2-indol-3-yl-ethyl)-naphthalen-2-ylmethylene-amine 在 5%-palladium/activated carbon 、 苯甲醚 作用下， 反应 24.0h， 生成 1-(naphthalen-2-yl)-9H-pyrido[3,4-b]indole
  参考文献：
  名称：

  Ru(II)-Catalyzed β-Carboline Directed C–H Arylation and Isolation of Its Cycloruthenated Intermediates

  摘要：

  A Ru(II)-catalyzed C-H arylation approach has been developed utilizing beta-carboline alkaloids as the directing group. Selective formations of diarylated products from moderate to excellent yields were accomplished. Broad substrate scope with excellent functional group tolerance for C1-phenyl/thienyl/PAHs-beta-carbolines was demonstrated. X-ray crystal structure of cycloruthenated complex 2cr and no arylation reaction with model substrate 13 strongly suggests that N2 is the directing group than N9 in C1-aryl-beta-carbolines. Catalytic properties and stability of the cycloruthenated complexes have been explored. Library of biologically relevant new,beta-carboline derivatives and isolation of its cycloruthenated intermediates are the highlights of this work

  DOI：

  10.1021/acs.joc.5b00411
• 作为产物：
  描述：

  色胺 、 2-萘甲醛 生成 (2-indol-3-yl-ethyl)-naphthalen-2-ylmethylene-amine
  参考文献：
  名称：

  铜催化化学选择性发散卡宾插入色胺的 N−H 键

  摘要：

  轻松获得具有化学选择性的不同产物在有机合成中非常重要。在此，我们开发了一种化学选择性铜催化卡宾插入色胺衍生物 N−H 键的方案。通过改变色胺的脂肪族NH与给电子或吸电子基团的亲核性来获得不同的插入产物。该反应以良好的产率提供了具有广泛底物范围的 NH 插入产物。

  DOI：

  10.1002/adsc.202300893

文献信息

• Reductive amination products containing naphthalene and indole moieties bind to melanocortin receptors
  作者：Felikss Mutulis、Ilze Mutule、Maris Lapins、Jarl E.S. Wikberg

  DOI：10.1016/s0960-894x(02)00088-4

  日期：2002.4

  Presumed pharmacophoric groups of melanocortin peptides (naphthalene, amino or guanidine, and indole moieties) were combined in mimetics molecules looking for their favorable location for activity at melanocortin (MC) receptors. Twenty-two compounds were prepared and tested. The best of these displayed micromolar affinities for the MC receptors. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Identification of Trypanosoma brucei leucyl-tRNA synthetase inhibitors by pharmacophore- and docking-based virtual screening and synthesis
  作者：Yaxue Zhao、Qing Wang、Qingqing Meng、Dazhong Ding、Huaiyu Yang、Guangwei Gao、Dawei Li、Weiliang Zhu、Huchen Zhou

  DOI：10.1016/j.bmc.2011.12.035

  日期：2012.2

  Human African trypanosomiasis (HAT), caused by the protozoan parasite Trypanosoma brucei, is a neglected fatal disease. Leucyl-tRNA synthetase (LeuRS), which has been successfully applied in the development of antifungal agent, represents a potential antiprotozoal drug target. In this study, a 3D model of T. brucei LeuRS (TbLeuRS) synthetic active site was constructed and subjected to virtual screening using a combination of pharmacophore- and docking-based methods. A new 2-pyrrolinone scaffold was discovered and the structure-activity relationship (SAR) studies aided by the docking model and organic synthesis were carried out. Compounds with various substituents on R-1, R-2 and R-3 were synthesized and their SAR was discussed. (C) 2012 Elsevier Ltd. All rights reserved.