4-[4-[2-[(3S)-3-hydroxyquinuclidin-3-yl]ethynyl]phenoxy]benzoic acid | 1316759-24-6

• 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: 4-[4-[2-[(3S)-3-hydroxyquinuclidin-3-yl]ethynyl]phenoxy]benzoic acid
• 英文别名: 4-[4-[2-[(3S)-3-hydroxy-1-azabicyclo[2.2.2]octan-3-yl]ethynyl]phenoxy]benzoic acid
• CAS: 1316759-24-6
• 化学式: C₂₂H₂₁NO₄
• 分子量: 363.413
• InChiKey: QYNYVCREJAXCIU-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  70
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[4-[2-[(3S)-3-hydroxyquinuclidin-3-yl]ethynyl]phenoxy]benzoic acid 、 4-氨甲基嘧啶 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以40%的产率得到4-[4-[2-[(3S)-3-hydroxyquinuclidin-3-yl]ethynyl]phenoxy]-N-(pyrimidin-4-ylmethyl)benzamide
  参考文献：
  名称：

  Selective non zinc binding inhibitors of MMP13

  摘要：

  Directed screening has identified a novel series of MMP13 inhibitors that possess good levels of activity whilst possessing excellent selectivity over related MMPs. The binding mode of the series has been solved by co-crystallisation and demonstrates an interesting mode of inhibition without interaction with the catalytic zinc atom. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.075
• 作为产物：
  描述：

  4-(4-溴苯氧基)苯甲酸甲酯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 水 、 三乙胺 、 三苯基膦 、 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 4-[4-[2-[(3S)-3-hydroxyquinuclidin-3-yl]ethynyl]phenoxy]benzoic acid
  参考文献：
  名称：

  Selective non zinc binding inhibitors of MMP13

  摘要：

  Directed screening has identified a novel series of MMP13 inhibitors that possess good levels of activity whilst possessing excellent selectivity over related MMPs. The binding mode of the series has been solved by co-crystallisation and demonstrates an interesting mode of inhibition without interaction with the catalytic zinc atom. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.075

文献信息

• Lead optimisation of selective non-zinc binding inhibitors of MMP13. Part 2
  作者：Chris De Savi、Andrew D. Morley、Ian Nash、Galith Karoutchi、Ken Page、Attilla Ting、Stefan Gerhardt

  DOI：10.1016/j.bmcl.2011.11.034

  日期：2012.1

  Directed screening has identified a novel series of non-zinc binding MMP13 inhibitors that possess good levels of activity whilst demonstrating excellent selectivity over related MMPs. A lead optimisation campaign has delivered compounds with enhanced MMP13 potency, good selectivity and acceptable bioavailability profiles leading to a predicted twice-a-day dosing regimen in man.
• Selective non zinc binding inhibitors of MMP13
  作者：Chris De Savi、Andrew D. Morley、Attilla Ting、Ian Nash、Kostas Karabelas、Christine M. Wood、Michael James、Stephen J. Norris、Galith Karoutchi、Neil Rankine、Gordon Hamlin、Philip A. MacFaul、David Ryan、Sarah V. Baker、David Hargreaves、Stefan Gerhardt

  DOI：10.1016/j.bmcl.2011.05.075

  日期：2011.7

  Directed screening has identified a novel series of MMP13 inhibitors that possess good levels of activity whilst possessing excellent selectivity over related MMPs. The binding mode of the series has been solved by co-crystallisation and demonstrates an interesting mode of inhibition without interaction with the catalytic zinc atom. (C) 2011 Elsevier Ltd. All rights reserved.