(3-endo)-3-iodomethyl-8-methyl-8-azabicyclo[3.2.1]octane | 850607-72-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 托烷生物碱
• 英文名称: (3-endo)-3-iodomethyl-8-methyl-8-azabicyclo[3.2.1]octane
• 英文别名: 3-iodomethyltropane；(endo)-3-iodomethyl-8-methyl-8-aza-bicyclo[3.2.1]octane；endo-3-iodomethyl-8-methyl-8-aza-bicyclo[3.2.1]octane
• CAS: 850607-72-6
• 化学式: C₉H₁₆IN
• 分子量: 265.137
• InChiKey: CQUHAAWGQNXDFT-AYMMMOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.29
• 重原子数：
  11.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (3-endo)-3-iodomethyl-8-methyl-8-azabicyclo[3.2.1]octane 、 三苯基甲烷 在 正丁基锂 、 水 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.17h， 生成 (3-endo)-8-methyl-3-(2,2,2-triphenylethyl)-8-azabicyclo[3.2.1]-octane
  参考文献：
  名称：

  Design, Synthesis, and Structure−Activity Relationship of Tropane Muscarinic Acetylcholine Receptor Antagonists

  摘要：

  Novel tropane derivatives were characterized as muscarinic acetylcholine receptor antagonists (mAChRs). Through optimization of the structure-activity relationship around the tropane scaffold, the quaternary ammonium salt 34 was identified as a very Potent M(3) mAChR antagonist. The compound was functionally active and displayed greater than 24 It duration of action in a mouse model of bronchoconstriction.

  DOI：

  10.1021/jm900736e
• 作为产物：
  描述：

  endo-(8-Methyl-8-azabicyclo[3.2.1]octan-3-yl)methanol 以77的产率得到(3-endo)-3-iodomethyl-8-methyl-8-azabicyclo[3.2.1]octane
  参考文献：
  名称：

  Muscarinic acetycholine receptor antagonists

  摘要：

  提供了肌动蛋白乙酰胆碱受体拮抗剂及其使用方法。

  公开号：

  US20070105895A1

文献信息

• [EN] NOVEL COMBINATION OF THERAPEUTIC AGENTS<br/>[FR] NOUVELLE COMBINAISON D'AGENTS THÉRAPEUTIQUES
  申请人：GLAXO GROUP LTD

  公开号：WO2009036243A1

  公开（公告）日：2009-03-19

  Novel combinations of a muscarinic acetylcholine receptor antagonist and a beta 2 agonist and/or a corticosteroid for inhaled administration via the nose or mouth, and methods of using them are provided herein.

  本文提供了一种新颖的肌肉收缩性乙酰胆碱受体拮抗剂与β2激动剂和/或皮质类固醇的组合，用于通过鼻腔或口腔进行吸入给药，并提供了使用它们的方法。
• [EN] M3 MUSCARINIC ACETYLCHOLINE RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES DU RECEPTEUR MUSCARINIQUE M3 DE L'ACETYLCHOLINE
  申请人：GLAXO GROUP LTD

  公开号：WO2005046586A3

  公开（公告）日：2005-07-28
• Discovery of (3-endo)-3-(2-cyano-2,2-diphenylethyl)-8,8-dimethyl-8-azoniabicyclo[3.2.1]octane bromide as an efficacious inhaled muscarinic acetylcholine receptor antagonist for the treatment of COPD
  作者：Zehong Wan、Dramane I. Laine、Hongxing Yan、Chongjie Zhu、Katherine L. Widdowson、Peter T. Buckley、Miriam Burman、James J. Foley、Henry M. Sarau、Dulcie B. Schmidt、Edward F. Webb、Kristen E. Belmonte、Michael Palovich

  DOI：10.1016/j.bmcl.2009.07.006

  日期：2009.8

  Design and syntheses of a novel series of muscarinic antagonists are reported. These efforts have culminated in the discovery of (3-endo)-3-(2-cyano-2,2-diphenylethyl)-8,8-dimethyl-8-azoniabicyclo[3.2.1]octane bromide (4a) as a potent and pan-active muscarinic antagonist as well as a functionally active compound in a murine model of bronchoconstriction. The compound has also displayed pharmacokinetic characteristics suitable for inhaled delivery. (C) 2009 Elsevier Ltd. All rights reserved.
• MUSCARINIC ACETYCHOLINE RECEPTOR ANTAGONISTS
  申请人：GLAXO GROUP LIMITED

  公开号：EP1677795B1

  公开（公告）日：2011-01-05
• M3 MUSCARINIC ACETYLCHOLINE RECEPTOR ANTAGONISTS
  申请人：GLAXO GROUP LIMITED

  公开号：EP1682142B1

  公开（公告）日：2012-07-11