ethyl 5-hydroxy-2-(2-hydroxy-3-(1-(5-phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-ylamino)propoxy)benzoate | 1041190-87-7

• 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: ethyl 5-hydroxy-2-(2-hydroxy-3-(1-(5-phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-ylamino)propoxy)benzoate
• 英文别名: ethyl 5-hydroxy-2-[2-hydroxy-3-[[1-(5-phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-yl]amino]propoxy]benzoate
• CAS: 1041190-87-7
• 化学式: C₂₉H₃₂N₄O₅S
• 分子量: 548.663
• InChiKey: CBEJBKOQJBHRKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  145
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  ethyl 5-hydroxy-2-(2-hydroxy-3-(1-(5-phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-ylamino)propoxy)benzoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 以19%的产率得到4-(2-hydroxy-3-(1-(5-phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-ylamino)propoxy)-3-(hydroxymethyl)phenol
  参考文献：
  名称：

  Thienopyrimidines as β3-adrenoceptor agonists: Hit-to-lead optimization

  摘要：

  Resulting from a vHTS based on a pharmacophore alignment on known beta 3-adrenoceptor ligands, an aryloxypropanolamine scaffold comprising a thienopyrimidine moiety was further optimized as a human beta 3-AR agonist, yielding a lead compound with an excellent cellular activity of EC(50) = 20 pM, selectivity over h beta 1- and h beta 2- adrenoceptors and a promising safety profile. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.039
• 作为产物：
  描述：

  C₃₁H₃₆N₄O₆S 在 对甲苯磺酸 作用下， 以 异丙醇 为溶剂， 反应 5.0h， 以36%的产率得到ethyl 5-hydroxy-2-(2-hydroxy-3-(1-(5-phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-ylamino)propoxy)benzoate
  参考文献：
  名称：

  Thienopyrimidines as β3-adrenoceptor agonists: Hit-to-lead optimization

  摘要：

  Resulting from a vHTS based on a pharmacophore alignment on known beta 3-adrenoceptor ligands, an aryloxypropanolamine scaffold comprising a thienopyrimidine moiety was further optimized as a human beta 3-AR agonist, yielding a lead compound with an excellent cellular activity of EC(50) = 20 pM, selectivity over h beta 1- and h beta 2- adrenoceptors and a promising safety profile. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.039

文献信息

• Aryloxypropanolamines, methods of preparation thereof and use of aryloxypropanolamines as medicaments
  申请人：4SC AG

  公开号：EP1947103A1

  公开（公告）日：2008-07-23

  This invention relates to novel aryloxypropanolamines. The invention also relates to the pharmaceutically acceptable salts and solvates containing said compounds, methods for the preparation thereof and to respective synthesis intermediates. Said compounds have agonistic activity at β3 adrenergic receptors and are useful for treatment of ailments influenced by activation of β3 adrenergic receptors.

  本发明涉及新型芳氧基丙醇胺。该发明还涉及含有所述化合物的药学上可接受的盐和溶剂化物，其制备方法以及相应的合成中间体。所述化合物在β3肾上腺素能受体上具有激动作用，并且可用于治疗受到β3肾上腺素能受体激活影响的疾病。
• ARYLOXYPROPANOLAMINES, METHODS OF PREPARATION THEROF AND USE OF ARYLOXYPROPANOLAMINES AS MEDICAMENTS
  申请人：Tasler Stefan

  公开号：US20080249114A1

  公开（公告）日：2008-10-09

  This invention relates to novel aryloxypropanolamines. The invention also relates to the pharmaceutically acceptable salts and solvates containing said compounds, methods for the preparation thereof and to respective synthetic intermediates. Said compounds have agonistic activity at β3 adrenergic receptors and are useful for treatment of ailments influenced by activation of β3 adrenergic receptors.

  本发明涉及新型芳氧基丙醇胺。该发明还涉及含有所述化合物的药学上可接受的盐和溶剂化合物，其制备方法以及相应的合成中间体。所述化合物在β3肾上腺素能受体上具有激动活性，并且可用于治疗受β3肾上腺素能受体激活影响的疾病。
• Aryloxypropanolamines, methods of preparation therof and use of aryloxypropanolamines as medicaments
  申请人：4SC AG

  公开号：US08207174B2

  公开（公告）日：2012-06-26

  This invention relates to novel aryloxypropanolamines. The invention also relates to the pharmaceutically acceptable salts and solvates containing said compounds, methods for the preparation thereof and to respective synthetic intermediates. Said compounds have agonistic activity at β3 adrenergic receptors and are useful for treatment of ailments influenced by activation of β3 adrenergic receptors.

  本发明涉及新颖的芳氧基丙醇胺。本发明还涉及含有该化合物的药学上可接受的盐和溶剂、其制备方法及相应的合成中间体。该化合物在β3肾上腺素能受体上具有激动作用，可用于治疗受β3肾上腺素能受体激活影响的疾病。
• ARYLOXYPROPANOLAMINES, METHODS OF PREPARATION THEREOF AND USE OF ARYLOXYPROPANOLAMINES AS MEDICAMENTS
  申请人：4SC AG

  公开号：EP2118086A1

  公开（公告）日：2009-11-18
• US8207174B2
  申请人：——

  公开号：US8207174B2

  公开（公告）日：2012-06-26