ethyl 1-(4-trifluoromethylbenzyl)-1H-indole-2-carboxylate | 866236-21-7

• 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: ethyl 1-(4-trifluoromethylbenzyl)-1H-indole-2-carboxylate
• 英文别名: 1-(4-trifluoromethylbenzyl)-1H-indole-2-carboxylic acid ethyl ester；ethyl 1-[[4-(trifluoromethyl)phenyl]methyl]indole-2-carboxylate
• CAS: 866236-21-7
• 化学式: C₁₉H₁₆F₃NO₂
• 分子量: 347.337
• InChiKey: KIRMBIMJAZHQEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 1-(4-trifluoromethylbenzyl)-1H-indole-2-carboxylate 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以99%的产率得到1-(4-trifluoromethylbenzyl)-1H-indole-2-carboxylic acid
  参考文献：
  名称：

  Identification of indole scaffold-based dual inhibitors of NOD1 and NOD2

  摘要：

  NOD1 and NOD2 are important members of the pattern recognition receptor family and play a crucial role within the context of innate immunity. However, overactivation of NODs, especially of NOD1, has also been implicated in a number of diseases. Surprisingly, NOD1 remains a virtually unexploited target in this respect. To gain additional insight into the structure-activity relationships of NOD1 inhibitors, a series of novel analogs has been designed and synthesized and then screened for their NOD1-inhibitory activity. Selected compounds were also investigated for their NOD2-inhibitory activity. Two compounds 4 and 15, were identified as potent mixed inhibitors of NOD1 and NOD2, displaying a balanced inhibitory activity on both targets in the low micromolar range. The results obtained have enabled a deeper understanding of the structural requirements for NOD1 and NOD2 inhibition. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.08.044
• 作为产物：
  描述：

  吲哚-2-羧酸 在 氯化亚砜 、 caesium carbonate 作用下， 以 乙腈 为溶剂， 生成 ethyl 1-(4-trifluoromethylbenzyl)-1H-indole-2-carboxylate
  参考文献：
  名称：

  Identification of indole scaffold-based dual inhibitors of NOD1 and NOD2

  摘要：

  NOD1 and NOD2 are important members of the pattern recognition receptor family and play a crucial role within the context of innate immunity. However, overactivation of NODs, especially of NOD1, has also been implicated in a number of diseases. Surprisingly, NOD1 remains a virtually unexploited target in this respect. To gain additional insight into the structure-activity relationships of NOD1 inhibitors, a series of novel analogs has been designed and synthesized and then screened for their NOD1-inhibitory activity. Selected compounds were also investigated for their NOD2-inhibitory activity. Two compounds 4 and 15, were identified as potent mixed inhibitors of NOD1 and NOD2, displaying a balanced inhibitory activity on both targets in the low micromolar range. The results obtained have enabled a deeper understanding of the structural requirements for NOD1 and NOD2 inhibition. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.08.044

文献信息

• PHARMACEUTICAL COMPOSITION AND METHOD
  申请人：Slade Rachel M.

  公开号：US20090155903A1

  公开（公告）日：2009-06-18

  The invention provides compounds, pharmaceutical compositions and methods for the therapeutic treatment and prevention of neurodegenerative disorder and other Aβ 42 -related diseases and disorders.

  该发明提供了化合物、制药组合物和方法，用于治疗和预防神经退行性疾病和其他与Aβ42相关的疾病和障碍。
• Design and synthesis of novel N-sulfonyl-2-indole carboxamides as potent PPAR-γ binding agents with potential application to the treatment of osteoporosis
  作者：Corey R. Hopkins、Steven V. O’Neil、Michael C. Laufersweiler、Yili Wang、Matthew Pokross、Marlene Mekel、Artem Evdokimov、Richard Walter、Maria Kontoyianni、Maria E. Petrey、Georgios Sabatakos、Jeff T. Roesgen、Eloise Richardson、Thomas P. Demuth

  DOI：10.1016/j.bmcl.2006.08.003

  日期：2006.11

  The synthesis and structure-activity relationships of a novel series of N-sulfonyl-2-indole carboxamides that bind to peroxisome proliferator-activated receptor gamma (PPAR-gamma) are reported. Chemical optimization of the series led to the identification of 4q (IC(50)=50 nM) as a potent binding agent of PPAR-gamma. Also reported is preliminary cell based data suggesting the use of these compounds in the treatment of osteoporosis.
• [EN] COMPOUNDS FOR NEURODEGENERATIVE DISORDERS<br/>[FR] COMPOSES DESTINES AUX TROUBLES NEURODEGENERATIFS
  申请人：MYRIAD GENETICS INC

  公开号：WO2005092062A2

  公开（公告）日：2005-10-06

  The invention provides compounds, pharmaceutical compositions and methods for the therapeutic treatment and prevention of neurodegenerative disorders and other Aβ42-related diseases and disorders.
• [EN] SUBSTITUTED INDOLE AND ITS DERIVATIVES AS CANNABINOID MODULATORS<br/>[FR] INDOLE SUBSTITUE ET SES DERIVES UTILISES EN TANT QUE MODULATEURS DE CANNABINOIDES
  申请人：CADILA HEALTHCARE LTD

  公开号：WO2009063495A2

  公开（公告）日：2009-05-22

  The present invention relates to novel substituted indole and indole derivatives to pharmaceutical compositions comprising the same, and to uses thereof. Compounds of the invention share pharmacological properties with cannabinoids and have a common wide range of beneficial therapeutic indications, hi particular, compounds of the invention are useful analgesic and anti-inflammatory agents by modulating the CB2 receptor.
• Identification of indole scaffold-based dual inhibitors of NOD1 and NOD2
  作者：Kaja Keček Plešec、Dunja Urbančič、Martina Gobec、Aleksandra Pekošak、Tihomir Tomašič、Marko Anderluh、Irena Mlinarič-Raščan、Žiga Jakopin

  DOI：10.1016/j.bmc.2016.08.044

  日期：2016.11

  NOD1 and NOD2 are important members of the pattern recognition receptor family and play a crucial role within the context of innate immunity. However, overactivation of NODs, especially of NOD1, has also been implicated in a number of diseases. Surprisingly, NOD1 remains a virtually unexploited target in this respect. To gain additional insight into the structure-activity relationships of NOD1 inhibitors, a series of novel analogs has been designed and synthesized and then screened for their NOD1-inhibitory activity. Selected compounds were also investigated for their NOD2-inhibitory activity. Two compounds 4 and 15, were identified as potent mixed inhibitors of NOD1 and NOD2, displaying a balanced inhibitory activity on both targets in the low micromolar range. The results obtained have enabled a deeper understanding of the structural requirements for NOD1 and NOD2 inhibition. (C) 2016 Elsevier Ltd. All rights reserved.