(3-endo)-3-(3-hydroxy-2,2-diphenylpropyl)-8,8-dimethyl-8-azoniabicyclo[3.2.1]octane bromide | 1182100-66-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3-endo)-3-(3-hydroxy-2,2-diphenylpropyl)-8,8-dimethyl-8-azoniabicyclo[3.2.1]octane bromide
• CAS: 1182100-66-8
• 化学式: Br*C₂₄H₃₂NO
• 分子量: 430.428
• InChiKey: SOXXQXVGPUWVOY-XITXYIRHSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.38
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  3-[(3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl]-2,2-diphenyl-1-propanol 在 溴甲烷 作用下， 生成 (3-endo)-3-(3-hydroxy-2,2-diphenylpropyl)-8,8-dimethyl-8-azoniabicyclo[3.2.1]octane bromide
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2009.07.006

文献信息

• Design, Synthesis, and Structure−Activity Relationship of Tropane Muscarinic Acetylcholine Receptor Antagonists
  作者：Dramane I. Lainé、Zehong Wan、Hongxing Yan、Chongjie Zhu、Haibo Xie、Wei Fu、Jakob Busch-Petersen、Christopher Neipp、Roderick Davis、Katherine L. Widdowson、Frank E. Blaney、James Foley、Alicia M. Bacon、Edward F. Webb、Mark A. Luttmann、Miriam Burman、Henry M. Sarau、Michael Salmon、Michael R. Palovich、Kristen Belmonte

  DOI：10.1021/jm900736e

  日期：2009.8.27

  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.
• 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.