3-[3-({7-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]heptyl}oxy)prop-1-ynyl]benzenesulfonamide | 452340-35-1

• 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: 3-[3-({7-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]heptyl}oxy)prop-1-ynyl]benzenesulfonamide
• 英文别名: 3-[3-[7-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]heptoxy]prop-1-ynyl]benzenesulfonamide
• CAS: 452340-35-1
• 化学式: C₂₉H₃₆N₂O₇S
• 分子量: 556.68
• InChiKey: KOTOQLJOZDYMLF-MHZLTWQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  126
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-[3-({7-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]heptyl}oxy)prop-1-ynyl]benzenesulfonamide 在 platinum(IV) oxide 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 3-[3-({7-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]heptyl}oxy)propyl]benzenesulfonamide
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of Long-acting β₂ Adrenergic Receptor Agonists Incorporating Arylsulfonamide Groups

  摘要：

  A series of saligenin alkoxyalkylphenylsulfonamide beta(2) adrenoceptor agonists were prepared by reacting a protected saligenin oxazolidinone with alkynyloxyalkyl bromides, followed by Sonogashira reaction, hydrogenation, and deprotection. The meta-substituted primary sulfonamide was more potent than the para and the ortho-analogues. Primary sulfonamides were more potent than the secondary and tertiary analogues. The onset and duration of action in vitro of selected compounds was assessed on isolated superfused guinea pig trachea. Sulfonamide 29b had the best profile of potency, selectivity, onset, and duration of action on both guinea pig trachea and human bronchus. Furthermore, 29b was found to have low oral bioavailability in rat and dog and also to have long duration of action in an in vivo model of bronchodilation. Crystalline salts of 29b were identified that had suitable properties for inhaled administration. A proposed binding mode for 29b to the beta(2)-receptor is presented.

  DOI：

  10.1021/jm801016j
• 作为产物：
  描述：

  (5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-3-[7-(prop-2-ynyloxy)heptyl]-1,3-oxazolidin-2-one 、 3-碘苯磺酰胺 在 copper(l) iodide 、 bis(tri-phenylphosphine)palladium(II) dichloride 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 17.0h， 生成 3-[3-({7-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]heptyl}oxy)prop-1-ynyl]benzenesulfonamide
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of Long-acting β₂ Adrenergic Receptor Agonists Incorporating Arylsulfonamide Groups

  摘要：

  A series of saligenin alkoxyalkylphenylsulfonamide beta(2) adrenoceptor agonists were prepared by reacting a protected saligenin oxazolidinone with alkynyloxyalkyl bromides, followed by Sonogashira reaction, hydrogenation, and deprotection. The meta-substituted primary sulfonamide was more potent than the para and the ortho-analogues. Primary sulfonamides were more potent than the secondary and tertiary analogues. The onset and duration of action in vitro of selected compounds was assessed on isolated superfused guinea pig trachea. Sulfonamide 29b had the best profile of potency, selectivity, onset, and duration of action on both guinea pig trachea and human bronchus. Furthermore, 29b was found to have low oral bioavailability in rat and dog and also to have long duration of action in an in vivo model of bronchodilation. Crystalline salts of 29b were identified that had suitable properties for inhaled administration. A proposed binding mode for 29b to the beta(2)-receptor is presented.

  DOI：

  10.1021/jm801016j

文献信息

• Phenethanolamine derivatives for treatment of respiratory diseases
  申请人：——

  公开号：US20040180876A1

  公开（公告）日：2004-09-16

  The present invention relates to novel compounds of Formula (I), to a process for their manufacture, to pharmaceutical compositions containing them, and to their use in therapy, in particular their use in the prophylaxis and treatment of respiratory diseases.

  本发明涉及一种新型化合物(I)、其制造方法、包含它们的药物组合物以及它们在治疗中的应用，特别是在呼吸系统疾病的预防和治疗中的应用。
• PHENETHANOLAMINE DERIVATIVES FOR TREATMENT OF RESPIRATORY DISEASES
  申请人：BIGGADIKE Keith

  公开号：US20060287286A1

  公开（公告）日：2006-12-21

  The present invention relates to novel compounds of Formula (I), to a process for their manufacture, to pharmaceutical compositions containing them, and to their use in therapy, in particular their use in the prophylaxis and treatment of respiratory diseases.

  本发明涉及式(I)的新化合物、其制备方法、含有它们的制药组合物以及它们在治疗中的应用，特别是它们在预防和治疗呼吸系统疾病中的应用。
• Methods using phenethanolamine derivatives for treatment of respiratory diseases
  申请人：Biggadike Keith

  公开号：US20070004807A1

  公开（公告）日：2007-01-04

  The present invention relates to novel compounds of Formula (I), to a process for their manufacture, to pharmaceutical compositions containing them, and to their use in therapy, in particular their use in the prophylaxis and treatment of respiratory diseases.

  本发明涉及式(I)的新化合物、其制造方法、含有它们的药物组合物，以及它们在治疗中的应用，特别是在呼吸系统疾病的预防和治疗中的应用。
• US7135600B2
  申请人：——

  公开号：US7135600B2

  公开（公告）日：2006-11-14
• US7442719B2
  申请人：——

  公开号：US7442719B2

  公开（公告）日：2008-10-28