(R,R)-2-naphthylfenoterol | 1219495-14-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R,R)-2-naphthylfenoterol
• 英文别名: (R,R)-5-(1-hydroxy-2-(1-(naphthalen-2-yl)propan-2-ylamino)ethyl)benzene-1,3-diol；5-[(1R)-1-hydroxy-2-[[(2R)-1-naphthalen-2-ylpropan-2-yl]amino]ethyl]benzene-1,3-diol
• CAS: 1219495-14-3
• 化学式: C₂₁H₂₃NO₃
• 分子量: 337.419
• InChiKey: LGUXLVJQUKRZBO-SZNDQCEHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  72.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R,R)-2-naphthylfenoterol 、 富马酸 以 乙醇 、 异丙醇 为溶剂， 生成 (R,R)-5-(1-hydroxy-2-(1-(naphthalen-2-yl)propan-2-ylamino)ethyl)benzene-1,3-diol fumarate
  参考文献：
  名称：

  Comparative molecular field analysis of fenoterol derivatives: A platform towards highly selective and effective β2-adrenergic receptor agonists

  摘要：

  Purpose: To use a previously developed CoMFA model to design a series of new structures of high selectivity and efficacy towards the beta(2)-adrenergic receptor. Results: Out of 21 computationally designed structures 6 compounds were synthesized and characterized for beta(2)-AR binding affinities, subtype selectivities and functional activities. Conclusion: the best compound is (R,R)-4-methoxy-1-naphthylfelnoterol with K-i beta(2)-AR = 0.28 mu m, K-i beta(1)-AR/K-i beta(2)-AR = 573, EC50cAMP = 3.9 nm, EC50cardio = 16 nm. The CoMFA model appears to be an effective predictor of the cardiomocyte contractility of the studied compounds which are targeted for use in congestive heart failure. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.11.062
• 作为产物：
  描述：

  在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以186 mg的产率得到(R,R)-2-naphthylfenoterol
  参考文献：
  名称：

  Comparative molecular field analysis of fenoterol derivatives: A platform towards highly selective and effective β2-adrenergic receptor agonists

  摘要：

  Purpose: To use a previously developed CoMFA model to design a series of new structures of high selectivity and efficacy towards the beta(2)-adrenergic receptor. Results: Out of 21 computationally designed structures 6 compounds were synthesized and characterized for beta(2)-AR binding affinities, subtype selectivities and functional activities. Conclusion: the best compound is (R,R)-4-methoxy-1-naphthylfelnoterol with K-i beta(2)-AR = 0.28 mu m, K-i beta(1)-AR/K-i beta(2)-AR = 573, EC50cAMP = 3.9 nm, EC50cardio = 16 nm. The CoMFA model appears to be an effective predictor of the cardiomocyte contractility of the studied compounds which are targeted for use in congestive heart failure. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.11.062

文献信息

• Comparative molecular field analysis of fenoterol derivatives: A platform towards highly selective and effective β2-adrenergic receptor agonists
  作者：Krzysztof Jozwiak、Anthony Yiu-Ho Woo、Mary J. Tanga、Lawrence Toll、Lucita Jimenez、Joseph A. Kozocas、Anita Plazinska、Rui-Ping Xiao、Irving W. Wainer

  DOI：10.1016/j.bmc.2009.11.062

  日期：2010.1

  Purpose: To use a previously developed CoMFA model to design a series of new structures of high selectivity and efficacy towards the beta(2)-adrenergic receptor. Results: Out of 21 computationally designed structures 6 compounds were synthesized and characterized for beta(2)-AR binding affinities, subtype selectivities and functional activities. Conclusion: the best compound is (R,R)-4-methoxy-1-naphthylfelnoterol with K-i beta(2)-AR = 0.28 mu m, K-i beta(1)-AR/K-i beta(2)-AR = 573, EC50cAMP = 3.9 nm, EC50cardio = 16 nm. The CoMFA model appears to be an effective predictor of the cardiomocyte contractility of the studied compounds which are targeted for use in congestive heart failure. (C) 2009 Elsevier Ltd. All rights reserved.