3-(4-tert-butyldimethylsilyloxyphenoxy)-2-(S)-propyleneoxide | 159182-09-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(4-tert-butyldimethylsilyloxyphenoxy)-2-(S)-propyleneoxide
• 英文别名: (S)-2-[[4-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]phenoxy]methyl]oxirane；tert-butyl-dimethyl-[4-[[(2S)-oxiran-2-yl]methoxy]phenoxy]silane
• CAS: 159182-09-9
• 化学式: C₁₅H₂₄O₃Si
• 分子量: 280.439
• InChiKey: XUXQPYCOHYDRSI-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.85
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  31
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-tert-butyldimethylsilyloxyphenoxy)-2-(S)-propyleneoxide 在 吡啶 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 (S)-N-[4-[2-[[2-hydroxy-3-(4-hydroxyphenoxy)propyl]amino]ethyl]phenyl]-4-iodobenzenesulfonamide
  参考文献：
  名称：

  Potent, selective benzenesulfonamide agonists of the human β3 adrenergic receptor

  摘要：

  A cloned human beta(3) adrenergic receptor assay was used to identify phenoxypropanolamine agonist 1. SAR studies led to the identification of benzenesulfonamide derivative 20, a 6.3 nM beta(3) agonist which shows 30-fold selectivity for beta(3) agonist activity over beta(1) and beta(2) receptor binding. Further refinement of this lead provided 4-bromo derivative 39, a subnanomolar agonist with 660-fold and 230-fold selectivity over beta(1) and beta(2), respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00169-3
• 作为产物：
  描述：

  4-(叔丁基二甲基硅氧基)苯酚 、 (S)-(+)- 间硝基苯磺酸缩水甘油酯 在 sodium hydride 作用下， 生成 3-(4-tert-butyldimethylsilyloxyphenoxy)-2-(S)-propyleneoxide
  参考文献：
  名称：

  Potent, selective benzenesulfonamide agonists of the human β3 adrenergic receptor

  摘要：

  A cloned human beta(3) adrenergic receptor assay was used to identify phenoxypropanolamine agonist 1. SAR studies led to the identification of benzenesulfonamide derivative 20, a 6.3 nM beta(3) agonist which shows 30-fold selectivity for beta(3) agonist activity over beta(1) and beta(2) receptor binding. Further refinement of this lead provided 4-bromo derivative 39, a subnanomolar agonist with 660-fold and 230-fold selectivity over beta(1) and beta(2), respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00169-3

文献信息

• Substituted phenyl sulfonamides as selective .beta. 3 agonists for the
  申请人：Merck & Co., Inc.

  公开号：US05451677A1

  公开（公告）日：1995-09-19

  Substituted phenylsulfonamides are selective .beta..sub.3 adrenergic receptor agonists with very little .beta..sub.1 and .beta..sub.2 adrenergic receptor activity and as such the compounds are capable of increasing lipolysis and energy expenditure in cells. The compounds thus have potent activity in the treatment of Type II diabetes and obesity. The compounds can also be used to lower triglyceride levels and cholesterol levels or raise high density lipoprotein levels or to decrease gut motility. In addition, the compounds can be used to reduced neurogenic inflammation or as antidepressant agents. The compounds are prepared by coupling an aminoalkylphenyl-sulfonamide with an appropriately substituted alkyl epoxide. Compositions and methods for the use of the compounds in the treatment of diabetes and obesity and for lowering triglyceride levels and cholesterol levels or raising high density lipoprotein levels or for increasing gut motility are also disclosed.

  取代苯磺酰胺是选择性的β3肾上腺素受体激动剂，几乎没有β1和β2肾上腺素受体活性，因此这些化合物能够增加细胞内脂解和能量消耗。因此，这些化合物在治疗2型糖尿病和肥胖症方面具有强大的活性。这些化合物还可以用于降低甘油三酯水平和胆固醇水平，或提高高密度脂蛋白水平，或减少肠道蠕动。此外，这些化合物可以用于减少神经源性炎症或作为抗抑郁剂。这些化合物是通过将氨基烷基苯磺酰胺与适当取代的烷基环氧化合物偶联而制备的。还公开了这些化合物在治疗糖尿病和肥胖症以及降低甘油三酯水平和胆固醇水平或提高高密度脂蛋白水平或增加肠道蠕动方面的用途的组合物和方法。
• NMDA RECEPTOR ANTAGONISTS FOR NEUROPROTECTION
  申请人：Emory University

  公开号：EP2170334B1

  公开（公告）日：2021-03-17