N-(2,2,2-三氟乙基)丙烷-1-胺 | 71113-54-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N-(2,2,2-三氟乙基)丙烷-1-胺
• 英文名称: Propyl(2,2,2-trifluoroethyl)amine
• 英文别名: N-(2,2,2-trifluoroethyl)propan-1-amine
• CAS: 71113-54-7
• 化学式: C₅H₁₀F₃N
• mdl: MFCD09941620
• 分子量: 141.136
• InChiKey: KSUNPCLRJWKSHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2,2,2-三氟乙基)丙烷-1-胺 在 三甲基铝 、 红铝 作用下， 以 甲苯 为溶剂， 反应 38.0h， 生成 Propyl-(2,2,2-trifluoro-ethyl)-[2-trifluoromethyl-9-(2,4,6-trimethyl-phenyl)-9H-benzo[d]imidazo[1,2-a]imidazol-3-ylmethyl]-amine
  参考文献：
  名称：

  Synthesis and structure–activity relationship of imidazo[1,2-a]benzimidazoles as corticotropin-releasing factor 1 receptor antagonists

  摘要：

  8-Aryl-1,3a,8-triaza-cyclopenta[a]indenes represent a novel series of high binding affinity corticotropin-releasing factor 1 receptor antagonists. Here, we report their synthesis, SAR, and pharmacokinetic properties of compound 8e (K-i = 23 nM). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.028

文献信息

• Synthesis, structure–activity relationships, and anxiolytic activity of 7-aryl-6,7-dihydroimidazoimidazole corticotropin-releasing factor 1 receptor antagonists
  作者：Xiaojun Han、Jodi A. Michne、Sokhom S. Pin、Kevin D. Burris、Lynn A. Balanda、Lawrence K. Fung、Tracey Fiedler、Kaitlin E. Browman、Matthew T. Taber、Jie Zhang、Gene M. Dubowchik

  DOI：10.1016/j.bmcl.2005.05.117

  日期：2005.9

  7-Aryl-6,7-dihydroimidazoimidazoles represent a novel series of high-affinity corticotropin-releasing factor 1 receptor antagonists. Here, we report their synthesis and SAR as well as behavioral activity of two exemplary compounds, 7b and 7k, in a mouse canopy model of anxiety.

  7-芳基-6,7-二氢咪唑并咪唑代表了一系列新的高亲和性促肾上腺皮质激素释放因子1受体拮抗剂。在这里，我们报告了它们的合成和SAR以及两个示例性化合物7b和7k在焦虑的小鼠冠层模型中的行为活性。
• Discovery of 6-chloro-2-trifluoromethyl-7-aryl-7H-imidazo[1,2-a]imidazol-3-ylmethylamines, a novel class of corticotropin-releasing factor receptor type 1 (CRF1R) antagonists
  作者：Dmitry Zuev、Vivekananda M. Vrudhula、Jodi A. Michne、Bireshwar Dasgupta、Sokhom S. Pin、Xiaohua Stella Huang、Dedong Wu、Qi Gao、Jie Zhang、Matthew T. Taber、John E. Macor、Gene M. Dubowchik

  DOI：10.1016/j.bmcl.2010.04.094

  日期：2010.6

  A novel series of [6-chloro-2-trifluoromethyl-7-aryl-7H-imidazo[1,2-a]imidazol-3-ylmethyl]-dialkylamines was discovered as potent CRF1R antagonists. The optimization of binding affinity in the series by the parallel reaction approach is discussed herein. (c) 2010 Elsevier Ltd. All rights reserved.
• 2-Aminopyrazolo[1,5-a]pyrimidines as potent and selective inhibitors of JAK2
  作者：Mark W. Ledeboer、Albert C. Pierce、John P. Duffy、Huai Gao、David Messersmith、Francesco G. Salituro、Suganthini Nanthakumar、Jon Come、Harmon J. Zuccola、Lora Swenson、Dina Shlyakter、Sudipta Mahajan、Thomas Hoock、Bin Fan、Wan-Jung Tsai、Elaine Kolaczkowski、Scott Carrier、James K. Hogan、Richard Zessis、S. Pazhanisamy、Youssef L. Bennani

  DOI：10.1016/j.bmcl.2009.10.053

  日期：2009.12

  Constitutive activation of the EPO/JAK2 signaling cascade has recently been implicated in a variety of myeloproliferative disorders including polycythemia vera, essential thrombocythemia and myelofibrosis. In an effort to uncover therapeutic potential of blocking the EPO/JAK2 signaling cascade, we sought to discover selective inhibitors that block the kinase activity of JAK2. Herein, we describe the discovery and structure based optimization of a novel series of 2-amino-pyrazolo[1,5-a]pyrimidines that exhibit potent inhibition of JAK2. (C) 2009 Elsevier Ltd. All rights reserved.
• Functionalized 6-(Piperidin-1-yl)-8,9-Diphenyl Purines as Peripherally Restricted Inverse Agonists of the CB1 Receptor
  作者：George Amato、Amruta Manke、Robert Wiethe、Vineetha Vasukuttan、Rodney Snyder、Yun Lan Yueh、Ann Decker、Scott Runyon、Rangan Maitra

  DOI：10.1021/acs.jmedchem.9b00727

  日期：2019.7.11

  Peripherally restricted CB1 receptor antagonists may be useful in treating metabolic syndrome, diabetes, liver diseases, and gastrointestinal disorders. Clinical development of the centrally acting CB1 inverse agonist otenabant (1) was halted due to its potential of producing adverse effects. SAR studies of 1 are reported herein with the objective of producing peripherally restricted analogues, Crystal structures of hCB1 and docking studies with 1 indicate that the piperidine group could be functionalized at the 4-position to access a binding pocket that can accommodate both polar and nonpolar groups. The piperidine is studied as a linker, functionalized with alkyl, heteroalkyl, aryl, and heteroaryl groups using a urea connector. Orally bioavailable and peripherally selective compounds have been produced that are potent inverse agonists of hCB1 with exceptional selectivity for hCB1 over hCB2. Compound 38 blocked alcohol-induced liver steatosis in mice and has good ADME properties for further development.