2-methyl-3-((1-t-butoxycarbonyl-2-(S)-pyrrolidinyl)methoxy)pyridine | 161417-35-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 2-methyl-3-((1-t-butoxycarbonyl-2-(S)-pyrrolidinyl)methoxy)pyridine
• 英文别名: tert-butyl (2S)-2-[(2-methylpyridin-3-yl)oxymethyl]pyrrolidine-1-carboxylate
• CAS: 161417-35-2
• 化学式: C₁₆H₂₄N₂O₃
• 分子量: 292.378
• InChiKey: NMGWCGBZEDOMAY-ZDUSSCGKSA-N

物化性质

• 沸点：
  394.5±22.0 °C(predicted)
• 密度：
  1.099±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  51.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methyl-3-((1-t-butoxycarbonyl-2-(S)-pyrrolidinyl)methoxy)pyridine 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.17h， 以88%的产率得到2-甲基-3-[[(2S)-吡咯烷-2-基]甲氧基]吡啶
  参考文献：
  名称：

  Structure−Activity Studies on 2-Methyl-3-(2(S)-pyrrolidinylmethoxy)pyridine (ABT-089):  An Orally Bioavailable 3-Pyridyl Ether Nicotinic Acetylcholine Receptor Ligand with Cognition-Enhancing Properties

  摘要：

  2-Methyl-3-(2(S)-pyrrolidinylmethoxy)pyridine, ABT-089 (S-4), a member of the 3-pyridyl ether class of nicotinic acetylcholine receptor (nAChR) ligands, shows positive effects in rodent and primate models of cognitive enhancement and a rodent model of anxiolytic activity and possesses a reduced propensity to activate peripheral ganglionic type receptors. The profiles of S-4, its N-methyl analogue, and the corresponding enantiomers across several measures of cholinergic channel function in vitro and in vivo are presented, together with in vitro. metabolism and in vivo bioavailability data. On the basis of its biological activities and favorable oral bioavailability, S-4 is an attractive candidate for further evaluation as a treatment for cognitive disorders.

  DOI：

  10.1021/jm960233u
• 作为产物：
  描述：

  3-羟基-2-甲基吡啶 、 N-Boc-L-脯氨醇 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以50%的产率得到2-methyl-3-((1-t-butoxycarbonyl-2-(S)-pyrrolidinyl)methoxy)pyridine
  参考文献：
  名称：

  Structure−Activity Studies on 2-Methyl-3-(2(S)-pyrrolidinylmethoxy)pyridine (ABT-089):  An Orally Bioavailable 3-Pyridyl Ether Nicotinic Acetylcholine Receptor Ligand with Cognition-Enhancing Properties

  摘要：

  2-Methyl-3-(2(S)-pyrrolidinylmethoxy)pyridine, ABT-089 (S-4), a member of the 3-pyridyl ether class of nicotinic acetylcholine receptor (nAChR) ligands, shows positive effects in rodent and primate models of cognitive enhancement and a rodent model of anxiolytic activity and possesses a reduced propensity to activate peripheral ganglionic type receptors. The profiles of S-4, its N-methyl analogue, and the corresponding enantiomers across several measures of cholinergic channel function in vitro and in vivo are presented, together with in vitro. metabolism and in vivo bioavailability data. On the basis of its biological activities and favorable oral bioavailability, S-4 is an attractive candidate for further evaluation as a treatment for cognitive disorders.

  DOI：

  10.1021/jm960233u

文献信息

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

  公开号：US05948793A1

  公开（公告）日：1999-09-07

  Novel heterocyclic ether compounds of the formula: ##STR1## wherein n, *, R.sup.1, R.sup.2, R.sup.3 and y are specifically defined, or pharmaceutically acceptable salts or prodrugs thereof, which are useful in selectively controlling neurotransmitter release; therapeutically-effective pharmaceutical compositions of these compounds; and use of said compositions to selectively control neurotransmitter release in mammals.

  新型杂环醚化合物的化学式为：##STR1## 其中n，*，R.sup.1，R.sup.2，R.sup.3和y具体定义，或其药学上可接受的盐或前药，可用于选择性控制神经递质释放；这些化合物的治疗有效药物组合物；以及利用所述组合物在哺乳动物中选择性控制神经递质释放。
• [EN] HETEROCYCLIC ETHER AND THIOETHER COMPOUNDS USEFUL IN CONTROLLING CHEMICAL SYNAPTIC TRANSMISSION<br/>[FR] COMPOSES ETHER ET THIOETHER HETEROCYCLIQUES UTILISES DANS LA REGULATION DE LA TRANSMISSION SYNAPTIQUE CHIMIQUE
  申请人：ABBOTT LABORATORIES

  公开号：WO1999032480A1

  公开（公告）日：1999-07-01

  (EN) Novel compounds having formulas (I), (II) or (III) or pharmaceutically-acceptable salts or prodrugs thereof, which are useful for controlling synaptic transmission; to therapeutically-effective pharmaceutical compositions of these compounds; and to the use of said compositions to controlling synaptic transmission in human or veterinary patients.(FR) L'invention porte sur de nouveaux composés ayant les formules (I), (II) ou (III), ou sur leurs sels pharmaceutiquement acceptables ou promédicaments, et qui sont utilisés dans la régulation de la transmission synaptique. L'invention porte également sur les compositions pharmaceutiques thérapeutiquement efficaces de ces composés, et sur l'utilisation de ces compositions pour réguler la transmission synaptique chez l'homme ou l'animal.

  （中文翻译）本发明涉及具有公式（I），（II）或（III）或其药学上可接受的盐或前药的新化合物，其用于控制突触传递；以及这些化合物的治疗有效的药物组合物，以及使用该组合物在人类或兽医患者中控制突触传递的用途。
• Synthesis and structure-activity relationships of pyridine-modified analogs of 3-[2-((S)-pyrrolidinyl)methoxy]pyridine, A-84543, a potent nicotinic acetylcholine receptor agonist
  作者：Nan-Horng Lin、David E Gunn、Yihong Li、Yun He、Hao Bai、Keith B Ryther、Theresa Kuntzweiler、Diana L Donnelly-Roberts、David J Anderson、Jeffrey E Campbell、James P Sullivan、Stephen P Arneric、Mark W Holladay

  DOI：10.1016/s0960-894x(98)00019-5

  日期：1998.2

  Analogs of 3-[2-((S)-pyrrolidinyl)methoxy]pyridine (A-84543, 1) with 2-, 4-, 5-, and 6-substituents on the pyridine ring were synthesized. These analogs exhibited Ki values ranging from 0.15 to > 9,000 nM when tested in vitro for neuronal nicotinic acetylcholine receptor binding activity. Assessment of functional activity at subtypes of neuronal nicotinic acetylcholine receptors indicates that pyridine substitution can have a profound effect on efficacy at these subtypes, and several subtype-selective agonists and antagonists have been identified. (C) 1998 Elsevier Science Ltd. All rights reserved.
• J. Med. Chem. 1997, 40, 385-390
  作者：

  DOI：——

  日期：——
• HETEROCYCLIC ETHER COMPOUNDS THAT ENHANCE COGNITIVE FUNCTION
  申请人：ABBOTT LABORATORIES

  公开号：EP0663912B1

  公开（公告）日：2001-12-12