5-methoxy-2-(phenylethynyl)quinoline | 1423778-31-7

• 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: 5-methoxy-2-(phenylethynyl)quinoline
• 英文别名: 5-Methoxy-2-(2-phenylethynyl)quinoline；5-methoxy-2-(2-phenylethynyl)quinoline
• CAS: 1423778-31-7
• 化学式: C₁₈H₁₃NO
• 分子量: 259.307
• InChiKey: JKTIXUXRNOXCFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-methoxyquinoline N-oxide 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 27.07h， 生成 5-methoxy-2-(phenylethynyl)quinoline
  参考文献：
  名称：

  Synthesis and In vivo Evaluation of 5-Methoxy-2-(phenylethynyl)quinoline (MPEQ) and [¹¹C]MPEQ Targeting Metabotropic Glutamate Receptor 5 (mGluR5)

  摘要：

  本文描述了5-甲氧基-2-(苯乙炔)喹啉（MPEQ 3）作为潜在的mGluR5选择性放射配体的合成和体内评估。我们已确定MPEQ 3在神经病理性疼痛动物模型中表现出镇痛效果。通过FDG/PET成像评估了MPEQ 3存在下mGluR5对大鼠大脑神经活动的影响。此外，关于[$^{11}C$]MPEQ 3的PET研究证明，[$^{11}C$]MPEQ 3在大鼠大脑中的积累与mGluR5的定位相关。

  DOI：

  10.5012/bkcs.2014.35.8.2304

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。
• Potassium Hydroxide-Catalyzed Alkynylation of Heteroaromatic N-Oxides with Terminal Alkynes
  作者：Xiaopei Chen、Fangfang Yang、Xiuling Cui、Yangjie Wu

  DOI：10.1002/adsc.201700931

  日期：2017.11.23

  An efficient potassium hydroxide‐catalyzed alkynylation of heteroaromatic N‐oxides under transition‐metal‐free conditions with the assistance of visible‐light has been developed. Various C2‐alkynylheterocycles were obtained in up to 92% yield with good functional group tolerance. This new method is operational simple, highly efficient, atom economic, and environmental friendly.

  在无过渡金属的条件下，借助可见光，已开发出一种有效的氢氧化钾催化的杂芳族N-氧化物的炔基化方法。获得了各种C2-炔基杂环，收率高达92％，并具有良好的官能团耐受性。这种新方法操作简单，高效，原子经济且环境友好。
• 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.
• US8946431B2
  申请人：——

  公开号：US8946431B2

  公开（公告）日：2015-02-03
• Synthesis and In vivo Evaluation of 5-Methoxy-2-(phenylethynyl)quinoline (MPEQ) and [¹¹C]MPEQ Targeting Metabotropic Glutamate Receptor 5 (mGluR5)
  作者：Ji Young Kim、Myung-Hee Son、Kihang Choi、Du-Jong Baek、Min Kyung Ko、Eun Jeong Lim、Ae Nim Pae、Gyochang Keum、Jae Kyun Lee、Yong Seo Cho、Hyunah Choo、Youn Woo Lee、Byung Seok Moon、Byung Cheol Lee、Ho-Young Lee、Sun-Joon Min

  DOI：10.5012/bkcs.2014.35.8.2304

  日期：2014.8.20

  The synthesis and in vivo evaluation of 5-methoxy-2-(phenylethynyl)quinoline (MPEQ) 3 as a potential mGluR5 selective radioligand is described. We have identified MPEQ 3 exhibiting the analgesic effect in the neuropathic pain animal model. The effect of mGluR5 on neuronal activity in rat brain was evaluated through FDG/PET imaging in the presence of MPEQ 3. In addition, the PET study of [$^11}C$]MPEQ 3 proved that accumulation of [$^11}C$]MPEQ 3 in rat brain was correlated to the localization of the mGluR5.

  本文描述了5-甲氧基-2-(苯乙炔)喹啉（MPEQ 3）作为潜在的mGluR5选择性放射配体的合成和体内评估。我们已确定MPEQ 3在神经病理性疼痛动物模型中表现出镇痛效果。通过FDG/PET成像评估了MPEQ 3存在下mGluR5对大鼠大脑神经活动的影响。此外，关于[$^11}C$]MPEQ 3的PET研究证明，[$^11}C$]MPEQ 3在大鼠大脑中的积累与mGluR5的定位相关。