2-((4-(adamantane-1-carbonyloxy)-2-ethylphenoxy)methyl)oxirane | 1041191-16-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 2-((4-(adamantane-1-carbonyloxy)-2-ethylphenoxy)methyl)oxirane
• 英文别名: [3-Ethyl-4-(oxiran-2-ylmethoxy)phenyl] adamantane-1-carboxylate；[3-ethyl-4-(oxiran-2-ylmethoxy)phenyl] adamantane-1-carboxylate
• CAS: 1041191-16-5
• 化学式: C₂₂H₂₈O₄
• 分子量: 356.462
• InChiKey: WNGLADKBZOXLBI-UHFFFAOYSA-N

物化性质

• 沸点：
  461.8±30.0 °C(Predicted)
• 密度：
  1.210±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  48.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(5-phenyl-thieno[2,3-d]pyrimidine-4-yl)-piperidin-4-ylamine 、 2-((4-(adamantane-1-carbonyloxy)-2-ethylphenoxy)methyl)oxirane 以 异丙醇 为溶剂， 生成 C₃₉H₄₆N₄O₄S
  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：

  4-(adamantane-1-carbonyloxy)-2-ethylphenol 、 环氧溴丙烷 在 potassium carbonate 作用下， 以 丁酮 为溶剂， 反应 42.0h， 以45%的产率得到2-((4-(adamantane-1-carbonyloxy)-2-ethylphenoxy)methyl)oxirane
  参考文献：
  名称：

  Aryloxypropanolamines, methods of preparation thereof and use of aryloxypropanolamines as medicaments

  摘要：

  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。

  公开号：

  EP1947103A1

文献信息

• 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 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
• [EN] ARYLOXYPROPANOLAMINES, METHODS OF PREPARATION THEREOF AND USE OF ARYLOXYPROPANOLAMINES AS MEDICAMENTS<br/>[FR] ARYLOXYPROPANOLAMINES, PROCÉDÉ DE FABRICATION DE CELLES-CI ET UTILISATION D'ARYLOXYPROPANOLAMINES COMME MÉDICAMENTS
  申请人：4SC AG

  公开号：WO2008090140A1

  公开（公告）日：2008-07-31

  [EN] 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 ß3 adrenergic receptors and are useful for treatment of ailments influenced by activation of ß3 adrenergic receptors.
  [FR] Cette invention porte sur de nouvelles aryloxypropanolamines. L'invention porte également sur des sels et des solvates pharmaceutiquement acceptables contenant lesdits composés ; sur des procédés permettant de les préparer ; et sur des intermédiaires de synthèse respectifs. Lesdits composés présentent une activité agoniste aux récepteurs adrénergiques ß3 et sont utiles dans le traitement d'affections influencées par l'activation des récepteurs adrénergiques ß3.
• Thienopyrimidines as β3-adrenoceptor agonists: Hit-to-lead optimization
  作者：Stefan Tasler、Roland Baumgartner、Astrid Ammendola、Josef Schachtner、Tanja Wieber、Marcus Blisse、Sandra Rath、Mirko Zaja、Philipp Klahn、Udo Quotschalla、Peter Ney

  DOI：10.1016/j.bmcl.2010.08.039

  日期：2010.10

  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.