2-(1-(R)-phenethyl)-2-(S)-azabicyclo[2.2.2]oct-5-ene-3-carboxylic acid benzyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(1-(R)-phenethyl)-2-(S)-azabicyclo[2.2.2]oct-5-ene-3-carboxylic acid benzyl ester
• 英文别名: 2-(1R-phenylethyl)-2-aza-bicyclo[2.2.2]oct-5-ene-3S-carboxylic acid benzyl ester；benzyl (3S)-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.2]oct-5-ene-3-carboxylate
• 化学式: C₂₃H₂₅NO₂
• 分子量: 347.457
• InChiKey: CQRLZQJXEBXYMN-BBGBUTGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1-(R)-phenethyl)-2-(S)-azabicyclo[2.2.2]oct-5-ene-3-carboxylic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 水 为溶剂， 23.0 ℃ 、275.79 kPa 条件下， 反应 2.0h， 生成 (S)-2-氮杂双环[2.2.2]辛烷-3-羧酸
  参考文献：
  名称：

  Selection of a 2-azabicyclo[2.2.2]octane-based α4β1 integrin antagonist as an inhaled anti-asthmatic agent

  摘要：

  The alpha(4)beta(1) integrin, expressed on eosinophils and neutrophils, induces inflammation in the lung by facilitating cellular infiltration and activation. From a number of potent alpha(4)beta(1) antagonists that we evaluated for safety and efficacy, 1 was selected as a lead candidate for anti-asthma therapy by the inhalation route. We devised an optimized stereoselective synthesis to facilitate the preparation of a sufficiently large quantity of 1 for assessment in vivo. Administration of 1 to allergen-sensitive sheep by inhalation blocked the late-phase response of asthma and abolished airway hyper-responsiveness at 24 h following the antigen challenge. Additionally, the recruitment of inflammatory cells into the lungs was inhibited. Administration of 1 to ovalbumin-sensitized guinea pigs intraperitoneally blocked airway resistance and inhibited the recruitment of inflammatory cells. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.01.067
• 作为产物：
  描述：

  dibenzyl (2R,3R)-2,3-dihydroxybutanedioate 在 高碘酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 69.5h， 生成 2-(1-(R)-phenethyl)-2-(S)-azabicyclo[2.2.2]oct-5-ene-3-carboxylic acid benzyl ester
  参考文献：
  名称：

  WO2008/73987

  摘要：

  公开号：

文献信息

• SATURATED FUSED [1,2-b]PYRIDAZINONE COMPOUNDS
  申请人：Ruebsam Frank

  公开号：US20080214529A1

  公开（公告）日：2008-09-04

  The invention is directed to saturated fused [1,2-b]pyridazinone compounds and pharmaceutical compositions containing such compounds that are useful in treating infections by hepatitis C virus.

  本发明涉及饱和融合[1,2-b]吡啶嗪化合物和含有这种化合物的制药组合物，其可用于治疗丙型肝炎病毒感染。