2-((5-(trifluoromethyl)pyridine-2-yl)ethynyl)quinoline | 1423778-58-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-((5-(trifluoromethyl)pyridine-2-yl)ethynyl)quinoline
• 英文别名: 2-[2-[5-(Trifluoromethyl)pyridin-2-yl]ethynyl]quinoline；2-[2-[5-(trifluoromethyl)pyridin-2-yl]ethynyl]quinoline
• CAS: 1423778-58-8
• 化学式: C₁₇H₉F₃N₂
• 分子量: 298.267
• InChiKey: CFJNYELXKMBQBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氯喹啉 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 2-((5-(trifluoromethyl)pyridine-2-yl)ethynyl)quinoline
  参考文献：
  名称：

  Synthesis and biological evaluation of 2-(arylethynyl)quinoline derivatives as mGluR5 antagonists for the treatment of neuropathic pain

  摘要：

  We described here the synthesis and biological evaluation of mGluR5 antagonists containing a quinoline ring structure. Using intracellular calcium mobilization assay (FDSS assay), we identified compound 5n, showing high inhibitory activity against mGluR5. In addition, it was found that compound 5n has excellent stability profile. Finally, this compound exhibited favorable analgesic effects in spinal nerve ligation model of neuropathic pain, which is comparable to gabapentin. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.12.056

文献信息

• 2-(Substituted ethynyl)quinoline Derivatives as mGLUr5 Antagonists
  申请人：Korea Institute of Science and Technology

  公开号：US20140206876A1

  公开（公告）日：2014-07-24

  Provided is a 2-(substituted ethynyl)quinoline derivative having an mGluR5 antagonistic activity and pharmaceutically acceptable salts thereof. The compound of the present invention can be useful as a medicament for treating and preventing mGluR5 receptor-mediated diseases such as Alzheimer's disease, senile dementia, Parkinson's disease, L-DOPA-induced dyskinesia, Huntington's chorea, amyotrophic lateral sclerosis, multiple sclerosis, schizophrenia, anxiety disorder, depression, neuropathic pain, drug dependence, fragile X syndrome, autism, migraine and gastroesophageal reflux disease (GERD).

  提供的是一种具有mGluR5拮抗活性和其药用盐的2-(取代乙炔基)喹啉衍生物。本发明的化合物可用作治疗和预防mGluR5受体介导的疾病，如阿尔茨海默病、老年性痴呆、帕金森病、L-多巴诱导的运动障碍、亨廷顿舞蹈症、肌萎缩侧索硬化、多发性硬化、精神分裂症、焦虑症、抑郁症、神经病性疼痛、药物依赖、脆性X综合征、自闭症、偏头痛和胃食管反流病（GERD）的药物。
• US8946431B2
  申请人：——

  公开号：US8946431B2

  公开（公告）日：2015-02-03
• Synthesis and biological evaluation of 2-(arylethynyl)quinoline derivatives as mGluR5 antagonists for the treatment of neuropathic pain
  作者：Myung-Hee Son、Ji Young Kim、Eun Jeong Lim、Du-Jong Baek、Kihang Choi、Jae Kyun Lee、Ae Nim Pae、Sun-Joon Min、Yong Seo Cho

  DOI：10.1016/j.bmcl.2012.12.056

  日期：2013.3

  We described here the synthesis and biological evaluation of mGluR5 antagonists containing a quinoline ring structure. Using intracellular calcium mobilization assay (FDSS assay), we identified compound 5n, showing high inhibitory activity against mGluR5. In addition, it was found that compound 5n has excellent stability profile. Finally, this compound exhibited favorable analgesic effects in spinal nerve ligation model of neuropathic pain, which is comparable to gabapentin. (c) 2012 Elsevier Ltd. All rights reserved.