3-[2-(2-allyl-4-(4-methoxycarbonylbutyl)phenyl)ethynyl]quinuclidin-3-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 奎宁环
• 英文名称: 3-[2-(2-allyl-4-(4-methoxycarbonylbutyl)phenyl)ethynyl]quinuclidin-3-ol
• 英文别名: 5-[3-Allyl-4-(3-hydroxy-1-aza-bicyclo[2.2.2]oct-3-ylethynyl)-phenyl]-pentanoic acid methyl ester；methyl 5-[4-[2-(3-hydroxy-1-azabicyclo[2.2.2]octan-3-yl)ethynyl]-3-prop-2-enylphenyl]pentanoate
• 化学式: C₂₄H₃₁NO₃
• 分子量: 381.515
• InChiKey: AUKBHEHVTGSWSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-(4-羟基苯基)戊酸甲酯 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 、 三乙胺 作用下， 以 二苯醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丁酮 为溶剂， 生成 3-[2-(2-allyl-4-(4-methoxycarbonylbutyl)phenyl)ethynyl]quinuclidin-3-ol
  参考文献：
  名称：

  Novel optimised quinuclidine squalene synthase inhibitors

  摘要：

  Optimised quinuclidine squalene synthase (SQS) inhibitors are reported; 3-[2-(2-allyl-4-(2-ethoxy carbonylethyl)phenyl)ethynyl]quinuclidin-3-ol 1c, is a potent inhibitor of rat (KI = 6 nM) and human (KI = 43 nM) microsomal SQS; the oral ED(50) of 1c, for the inhibition of rat cholesterol biosynthesis was 1.3+/-0.45 mg/kg and for the R-enantiomer 1m, 0.8+/-0.2 mg/kg, with the corresponding R-carboxylic acid 6a, being 0.9+/-0.25 mg/kg. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(97)00053-x

文献信息

• Novel optimised quinuclidine squalene synthase inhibitors
  作者：George R. Brown、Alan J. Foubister、Susan Freeman、Fergus McTaggart、Donald J. Mirrlees、Alan C. Reid、Graham J. Smith、Melvyn J. Taylor、Douglas A. Thomason、Paul R.O. Whittamore

  DOI：10.1016/s0960-894x(97)00053-x

  日期：1997.3

  Optimised quinuclidine squalene synthase (SQS) inhibitors are reported; 3-[2-(2-allyl-4-(2-ethoxy carbonylethyl)phenyl)ethynyl]quinuclidin-3-ol 1c, is a potent inhibitor of rat (KI = 6 nM) and human (KI = 43 nM) microsomal SQS; the oral ED(50) of 1c, for the inhibition of rat cholesterol biosynthesis was 1.3+/-0.45 mg/kg and for the R-enantiomer 1m, 0.8+/-0.2 mg/kg, with the corresponding R-carboxylic acid 6a, being 0.9+/-0.25 mg/kg. (C) 1997 Elsevier Science Ltd. All rights reserved.