2-(2-(S)-pyrrolidinyl)furo[3,2-b]pyridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡啶类
• 英文名称: 2-(2-(S)-pyrrolidinyl)furo[3,2-b]pyridine
• 英文别名: (S)-2-Pyrrolidin-2-yl-furo[3,2-b]pyridine；2-[(2S)-pyrrolidin-2-yl]furo[3,2-b]pyridine
• 化学式: C₁₁H₁₂N₂O
• 分子量: 188.229
• InChiKey: QULUBEZVAACGFX-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2S)-2-乙炔-1-吡咯烷羧酸-1,1-二甲基乙酯 在 copper(l) iodide 、 dichlorobis(triphenylphosphine)palladium 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 2-(2-(S)-pyrrolidinyl)furo[3,2-b]pyridine
  参考文献：
  名称：

  Novel 2-(2′-furo[3,2-b]pyridinyl) pyrrolidines: potent neuronal nicotinic acetylcholine receptor ligands

  摘要：

  A novel series of 2-(2'-furo[3,2-b]pyridinyl) pyrrolidines has been synthesized and evaluated as novel nicotinic acetylcholine receptor ligands. Changing the pyrrolidine stereochemistry and N-substitution pattern afforded analogs with K-i values ranging from 2.7 to 97 nM. Rubidium efflux studies revealed that these compounds had intrinsic activities ranging from 9-58% that of nicotine in the IMR-32 cell line and 6-81% in the K177 cell line. The N(Me)-2(S) analog 3a demonstrated good selectivity in the K177 cell line (alpha(4) beta(2) receptor) versus the IMR-32 cells (alpha(3) beta(x) receptor) and TE 671 cells (alpha(1) neuromuscular receptor), and was a partial agonist with an EC50 value of 141 nM in dopamine release assay using rat striatal slices. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10080-4

文献信息

• FUROPYRIDINE, THIENOPYRIDINE, PYRROLOPYRIDINE AND RELATED PYRIMIDINE, PYRIDAZINE AND TRIAZINE COMPOUNDS USEFUL IN CONTROLLING CHEMICAL SYNAPTIC TRANSMISSION
  申请人：Abbott Laboratories

  公开号：EP0842178B1

  公开（公告）日：2001-03-28
• US6001849A
  申请人：——

  公开号：US6001849A

  公开（公告）日：1999-12-14
• [EN] FUROPYRIDINE, THIENOPYRIDINE, PYRROLOPYRIDINE AND RELATED PYRIMIDINE, PYRIDAZINE AND TRIAZINE COMPOUNDS USEFUL IN CONTROLLING CHEMICAL SYNAPTIC TRANSMISSION<br/>[FR] FUROPYRIDINE, THIENOPYRIDINE, PYRROLOPYRIDINE ET COMPOSES CONNEXES A BASE DE PYRIMIDINE, DE PYRIDAZINE ET DE TRIAZINE UTILES POUR GERER LA TRANSMISSION SYNAPTIQUE PAR VOIE CHIMIQUE
  申请人：ABBOTT LABORATORIES

  公开号：WO1997005139A1

  公开（公告）日：1997-02-13

  (EN) Novel heterocyclic ether compounds having the formula (I) wherein A, m, R, X, Y1, Y2 and Y3 are specifically defined, which are useful in selectively controlling chemical synaptic transmission; therapeutically-effective pharmaceutical compositions thereof; and use of said compositions to selectively control synaptic transmission in mammals.(FR) Nouveaux composés d'éther hétérocyclique de formule (I) où A, m, R, X, Y1, Y2 et Y3 sont définis spécifiquement. Ces composés sont utiles pour gérer sélectivement la transmission synaptique par voie chimique. L'invention porte aussi sur des compositions pharmaceutiques de ces composés, efficaces sur le plan thérapeutique, ainsi que sur l'usage de ces compositions pour gérer sélectivement la transmission synaptique chez les mammifères.
• Novel 2-(2′-furo[3,2-b]pyridinyl) pyrrolidines: potent neuronal nicotinic acetylcholine receptor ligands
  作者：Richard L. Elliott、Keith B. Ryther、David J. Anderson、Marietta Piattoni-Kaplan、Theresa A. Kuntzweiler、Diana Donnelly-Roberts、Stephen P. Arneric、Mark W. Holladay

  DOI：10.1016/s0960-894x(97)10080-4

  日期：1997.11

  A novel series of 2-(2'-furo[3,2-b]pyridinyl) pyrrolidines has been synthesized and evaluated as novel nicotinic acetylcholine receptor ligands. Changing the pyrrolidine stereochemistry and N-substitution pattern afforded analogs with K-i values ranging from 2.7 to 97 nM. Rubidium efflux studies revealed that these compounds had intrinsic activities ranging from 9-58% that of nicotine in the IMR-32 cell line and 6-81% in the K177 cell line. The N(Me)-2(S) analog 3a demonstrated good selectivity in the K177 cell line (alpha(4) beta(2) receptor) versus the IMR-32 cells (alpha(3) beta(x) receptor) and TE 671 cells (alpha(1) neuromuscular receptor), and was a partial agonist with an EC50 value of 141 nM in dopamine release assay using rat striatal slices. (C) 1997 Elsevier Science Ltd.