(2E)-3-(4-溴苯基)-1-[4--4-甲氧基苯甲酰基)-1-哌嗪基]-2-丙烯-1-酮 | 1599432-08-2

• 物质功能分类: 生物化工 - 生化试剂 - 激动剂抑制剂
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 中文名称: (2E)-3-(4-溴苯基)-1-[4--4-甲氧基苯甲酰基)-1-哌嗪基]-2-丙烯-1-酮
• 中文别名: NIBR189抑制剂
• 英文名称: NIBR189
• 英文别名: (E)-3-(4-bromophenyl)-1-(4-(4-methoxybenzoyl)piperazin-1-yl)prop-2-en-1-one；(E)-3-(4-bromophenyl)-1-[4-(4-methoxybenzoyl)piperazin-1-yl]prop-2-en-1-one
• CAS: 1599432-08-2
• 化学式: C₂₁H₂₁BrN₂O₃
• 分子量: 429.313
• InChiKey: OFHXXBRBGWUOHR-NYYWCZLTSA-N

物化性质

• 沸点：
  639.7±55.0 °C(Predicted)
• 密度：
  1.403±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO 中≥42.9 mg/mL；不溶于水；不溶于乙醇

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为产物：
  描述：

  4-溴肉桂酸 、 1-(4-甲氧苯甲酰基)哌嗪 在 N-甲基吗啉 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以69%的产率得到(2E)-3-(4-溴苯基)-1-[4--4-甲氧基苯甲酰基)-1-哌嗪基]-2-丙烯-1-酮
  参考文献：
  名称：

  Identification and Characterization of Small Molecule Modulators of the Epstein–Barr Virus-Induced Gene 2 (EBI2) Receptor

  摘要：

  Oxysterols have recently been identified as natural ligands for a G protein-coupled receptor called EBI2 (aka GPR183) (Nature 2011, 475, 524; 519). EBI2 is highly expressed in immune cells (J. Biol. Chem. 2006, 281, 13199), and its activation has been shown to be critical for the adaptive immune response and has been genetically linked to autoimmune diseases such as type I diabetes (Nature 2010, 467, 460). Here we describe the isolation of a potent small molecule antagonist for the EBI2 receptor. First, we identified a small molecule agonist NIBR51 (1), which enabled 0 identification of inhibitors of receptor activation. One antagonist called NIBR127 (2) was used as a starting point for a medicinal chemistry. campaign, which yielded NIBR189 (4m). This compound was extensively characterized in binding and various functional signaling assays. Furthermore, we have used 4m to block migration of a monocyte cell line called U937, suggesting a functional role of the oxysterol/EBI2 pathway in these immune cells.

  DOI：

  10.1021/jm4019355

文献信息

• EBI2 MODULATORS
  申请人：SANFORD-BURNHAM MEDICAL RESEARCH INSTITUTE

  公开号：US20160214951A1

  公开（公告）日：2016-07-28

  Provided herein are small molecule Epstein-Barr virus-induced G-protein coupled receptor 2 (EBI2) modulator compounds, compositions comprising the compounds, and methods of using the compounds and compositions comprising the compounds. EBI2 is a therapeutic target for the treatment of a variety of diseases or conditions. In some embodiments, EBI2 is a therapeutic target for the treatment of diseases or conditions such as, but not limited to, autoimmune diseases or conditions, cancer, and cardiovascular disease.

  本文提供了小分子埃普斯坦-巴尔病毒诱导的G蛋白偶联受体2（EBI2）调节剂化合物，包括这些化合物的组合物，以及使用这些化合物和组合物的方法。EBI2是治疗多种疾病或病症的治疗靶点。在某些实施例中，EBI2是治疗自身免疫性疾病或病症、癌症和心血管疾病等疾病或病症的治疗靶点。
• US9776979B2
  申请人：——

  公开号：US9776979B2

  公开（公告）日：2017-10-03
• [EN] EBI2 MODULATORS<br/>[FR] MODULATEURS EBI2
  申请人：SANFORD BURNHAM MED RES INST

  公开号：WO2015048570A2

  公开（公告）日：2015-04-02

  Provided herein are small molecule Epstein-Barr virus-induced G-protein coupled receptor 2 (EBI2) modulator compounds, compositions comprising the compounds, and methods of using the compounds and compositions comprising the compounds.
• Identification and Characterization of Small Molecule Modulators of the Epstein–Barr Virus-Induced Gene 2 (EBI2) Receptor
  作者：Francois Gessier、Inga Preuss、Hong Yin、Mette M. Rosenkilde、Stephane Laurent、Ralf Endres、Yu A. Chen、Thomas H. Marsilje、Klaus Seuwen、Deborah G. Nguyen、Andreas W. Sailer

  DOI：10.1021/jm4019355

  日期：2014.4.24

  Oxysterols have recently been identified as natural ligands for a G protein-coupled receptor called EBI2 (aka GPR183) (Nature 2011, 475, 524; 519). EBI2 is highly expressed in immune cells (J. Biol. Chem. 2006, 281, 13199), and its activation has been shown to be critical for the adaptive immune response and has been genetically linked to autoimmune diseases such as type I diabetes (Nature 2010, 467, 460). Here we describe the isolation of a potent small molecule antagonist for the EBI2 receptor. First, we identified a small molecule agonist NIBR51 (1), which enabled 0 identification of inhibitors of receptor activation. One antagonist called NIBR127 (2) was used as a starting point for a medicinal chemistry. campaign, which yielded NIBR189 (4m). This compound was extensively characterized in binding and various functional signaling assays. Furthermore, we have used 4m to block migration of a monocyte cell line called U937, suggesting a functional role of the oxysterol/EBI2 pathway in these immune cells.