5-(6-hydroxy-1-hexynyl)-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)pyridine | 191161-35-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(6-hydroxy-1-hexynyl)-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)pyridine
• 英文别名: 5-(6-hydroxy-1-hexynyl)-3-(1-methyl-2(S)-pyrrolidinylmethoxy)pyridine；6-[5-((S)-1-Methyl-pyrrolidin-2-ylmethoxy)-pyridin-3-yl]-hex-5-yn-1-ol；6-[5-[[(2S)-1-methylpyrrolidin-2-yl]methoxy]pyridin-3-yl]hex-5-yn-1-ol
• CAS: 191161-35-0
• 化学式: C₁₇H₂₄N₂O₂
• 分子量: 288.39
• InChiKey: GJKKKELBGQEBIU-INIZCTEOSA-N

物化性质

• 沸点：
  458.2±40.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  45.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(6-hydroxy-1-hexynyl)-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)pyridine 在 咪唑 、 碘 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以92%的产率得到5-(6-iodo-1-hexynyl)-3-(1-methyl-2(S)-pyrrolidinylmethoxy)pyridine
  参考文献：
  名称：

  Novel Pyridyl Ring C5 Substituted Analogues of Epibatidine and 3-(1-Methyl-2(S)- pyrrolidinylmethoxy)pyridine (A-84543) as Highly Selective Agents for Neuronal Nicotinic Acetylcholine Receptors Containing β2 Subunits

  摘要：

  Introduction of a hydrophobic or hydrogen-bonding alkynyl group into the C5 position of the pyridyl ring of epibatidine and A-84543 significantly increased the selectivity for neuronal nicotinic acetylcholine receptors (nAChRs) containing beta 2 subunits over nACbRs containing beta 4 subunits (K-i ratio up to 92000-fold). Our data indicate that the extracellular domains of the nAChRs are sufficiently different to allow for the design of novel ligands with high affinity and selectivity for the nAChR subtypes.

  DOI：

  10.1021/jm0492406
• 作为产物：
  描述：

  N-甲基-L-脯氨醇 在 palladium on activated charcoal copper(l) iodide 、 sodium hydride 、 potassium carbonate 、 三苯基膦 作用下， 以 乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 122.0h， 生成 5-(6-hydroxy-1-hexynyl)-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)pyridine
  参考文献：
  名称：

  Novel Pyridyl Ring C5 Substituted Analogues of Epibatidine and 3-(1-Methyl-2(S)- pyrrolidinylmethoxy)pyridine (A-84543) as Highly Selective Agents for Neuronal Nicotinic Acetylcholine Receptors Containing β2 Subunits

  摘要：

  Introduction of a hydrophobic or hydrogen-bonding alkynyl group into the C5 position of the pyridyl ring of epibatidine and A-84543 significantly increased the selectivity for neuronal nicotinic acetylcholine receptors (nAChRs) containing beta 2 subunits over nACbRs containing beta 4 subunits (K-i ratio up to 92000-fold). Our data indicate that the extracellular domains of the nAChRs are sufficiently different to allow for the design of novel ligands with high affinity and selectivity for the nAChR subtypes.

  DOI：

  10.1021/jm0492406

文献信息

• 3-pyridyloxymethyl heterocyclic ether compounds useful in controlling
  申请人：Abbott Laboratories

  公开号：US05629325A1

  公开（公告）日：1997-05-13

  Novel 3-pyridyloxymethyl heterocyclic ether compounds of the formula: ##STR1## or the pharmaceutically-acceptable salts or prodrugs thereof are selective and potent ligands at neuronal nicotinic cholinergic channel receptors, and are effective in controlling synaptic transmission.

  新颖的3-吡啶基甲氧基杂环醚化合物，其化学公式如下：##STR1## 或其药用可接受的盐或前药，对神经元尼古丁胆碱能通道受体具有选择性和强效的配体作用，并且在控制突触传递方面是有效的。
• 3-Pyridyloxymethyl heterocyclic ether compounds useful in controlling
  申请人：Abbott Laboratories

  公开号：US06127386A1

  公开（公告）日：2000-10-03

  Novel 3-pyridyloxymethyl heterocyclic ether compounds of the formula: ##STR1## or the pharmaceutically-acceptable salts or prodrugs thereof are selective and potent ligands at neuronal nicotinic cholinergic channel receptors, and are effective in controlling synaptic transmission. Key intermediates and processes using this key intermediates to produce compounds of formula I with the variables defined in the specification are also described.

  3-吡啶基甲氧基杂环醚化合物的公式为：##STR1## 或其药用可接受盐或前药选择性高且强效地作用于神经元尼古丁胆碱能通道受体，并且在控制突触传递方面有效。还描述了使用这些关键中间体来生产本发说明书中定义的公式I化合物的重要中间体和过程。
• Ligands for Nicotinic Acetylcholine Receptors, and Methods of Making and Using Them
  申请人：Kozikowski Alan P.

  公开号：US20080132486A1

  公开（公告）日：2008-06-05

  One aspect of the present invention relates to heterocyclic compounds that are ligands for nicotinic acetylcholine receptors. A second aspect of the invention relates to the use of a compound of the invention for modulation of a mammalian nicotinic acetylcholine receptor. The present invention also relates to the use of a compound of the invention for treating a mammal suffering from Alzheimer's disease, Parkinson's disease, dyskinesias, Tourette's syndrome, schizophrenia, attention deficit disorder, anxiety, pain, depression, obsessive compulsive disorder, chemical substance abuse, alcoholism, memory deficit, pseudodementia, Ganser's syndrome, migraine pain, bulimia, obesity, premenstrual syndrome or late luteal phase syndrome, tobacco abuse, post-traumatic syndrome, social phobia, chronic fatigue syndrome, premature ejaculation, erectile difficulty, anorexia nervosa, disorders of sleep, autism, mutism or trichtillomania.

  本发明的一个方面涉及杂环化合物，其是乙酰胆碱受体的配体。本发明的第二个方面涉及使用本发明的化合物来调节哺乳动物的乙酰胆碱受体。本发明还涉及使用本发明的化合物来治疗患有阿尔茨海默病、帕金森病、运动障碍、抽动症、精神分裂症、注意力缺陷障碍、焦虑、疼痛、抑郁症、强迫症、化学物质滥用、酗酒、记忆力障碍、假性痴呆、甘瑟综合征、偏头痛疼痛、贪食症、肥胖症、月经前综合征或黄体酮期后综合征、烟草滥用、创伤后应激障碍、社交恐惧症、慢性疲劳综合征、早泄、勃起障碍、厌食症、睡眠障碍、自闭症、哑症或拔毛癖的哺乳动物。
• Ligands for nicotinic acetylcholine receptors, and methods of making and using them
  申请人：Georgetown University

  公开号：US08030300B2

  公开（公告）日：2011-10-04

  One aspect of the present invention relates to heterocyclic compounds that are ligands for nicotinic acetylcholine receptors. A second aspect of the invention relates to the use of a compound of the invention for modulation of a mammalian nicotinic acetylcholine receptor. The present invention also relates to the use of a compound of the invention for treating a mammal suffering from Alzheimer's disease, Parkinson's disease, dyskinesias, Tourette's syndrome, schizophrenia, attention deficit disorder, anxiety, pain, depression, obsessive compulsive disorder, chemical substance abuse, alcoholism, memory deficit, pseudodementia, Ganser's syndrome, migraine pain, bulimia, obesity, premenstrual syndrome or late luteal phase syndrome, tobacco abuse, post-traumatic syndrome, social phobia, chronic fatigue syndrome, premature ejaculation, erectile difficulty, anorexia nervosa, disorders of sleep, autism, mutism or trichtillomania.

  本发明的一个方面涉及杂环化合物，其是乙酰胆碱受体的配体。本发明的第二个方面涉及使用本发明的化合物来调节哺乳动物的乙酰胆碱受体。本发明还涉及使用本发明的化合物来治疗患有阿尔茨海默病、帕金森病、运动障碍、抽动症、精神分裂症、注意力缺陷障碍、焦虑、疼痛、抑郁、强迫症、化学物质滥用、酗酒、记忆力缺失、假性痴呆、甘瑟综合征、偏头痛、贪食症、肥胖症、经前期综合征或晚期黄体期综合征、烟草滥用、创伤后综合征、社交恐惧症、慢性疲劳综合征、早泄、勃起障碍、厌食症、睡眠障碍、自闭症、缄默症或拔毛癖的哺乳动物。
• [EN] LIGANDS FOR NICOTINIC ACETYLCHOLINE RECEPTORS, AND METHODS OF MAKING AND USING THEM<br/>[FR] LIGANDS POUR LES RECEPTEURS DE L'ACETYLCHOLINE NICOTINIQUE, ET PROCEDES DE PRODUCTION ET D'UTILISATION DE CES LIGANDS
  申请人：UNIV GEORGETOWN

  公开号：WO2005000806A3

  公开（公告）日：2005-03-24