{3-[({[2-(trimethylsilyl)ethyl]oxy}methyl)oxy]phenyl}methanol | 188875-63-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: {3-[({[2-(trimethylsilyl)ethyl]oxy}methyl)oxy]phenyl}methanol
• 英文别名: [3-(2-trimethylsilanylethoxy-methoxy)-phenyl]-methanol；(3-{[2-(trimethylsilyl)ethoxy]methoxy}phenyl)methanol；[3-(2-trimethylsilylethoxymethoxy)phenyl]methanol
• CAS: 188875-63-0
• 化学式: C₁₃H₂₂O₃Si
• 分子量: 254.401
• InChiKey: MVRJMONUWNTPIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  {3-[({[2-(trimethylsilyl)ethyl]oxy}methyl)oxy]phenyl}methanol 在 甲基磺酰氯 、 N,N-二异丙基乙胺 、 四丁基溴化铵 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 20.5h， 生成 3-{[2-(trimethylsilyl)ethoxy]methoxy}benzyl bromide
  参考文献：
  名称：

  [EN] PHENETANOLAMINE DERIVATIVES
  [FR] DERIVES DE PHENETANOLAMINE

  摘要：

  化合物的化学式(I)及其盐、溶剂合物和生理功能衍生物，可用于预防或治疗需要选择性β2-肾上腺素受体激动剂的临床病症，例如哮喘或慢性阻塞性肺疾病（COPD）。

  公开号：

  WO2005044787A1
• 作为产物：
  描述：

  3-羟基苯甲醇 、 2-(三甲基硅烷基)乙氧甲基氯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 2.42h， 生成 {3-[({[2-(trimethylsilyl)ethyl]oxy}methyl)oxy]phenyl}methanol
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of Long-acting β₂ Adrenergic Receptor Agonists Incorporating Metabolic Inactivation: An Antedrug Approach

  摘要：

  A series of saligenin beta(2) adrenoceptor agonist antedrugs having high clearance were prepared by reacting a protected saligenin oxazolidinone with protected hydroxyethoxyalkoxyalkyl bromides, followed by removal of the hydroxy-protecting group, alkylation, and final deprotection. The compounds were screened for beta(2), beta(1), and beta(3) agonist activity in CHO cells. The onset and duration of action in vitro of selected compounds were assessed on isolated superfused guinea pig trachea. Compound 13f had high potency, selectivity, fast onset, and long duration of action in vitro and was found to have long duration in vivo, low oral bioavailability in the rat, and to be rapidly metabolized. Crystalline salts of 13f (vilanterol) were identified that had suitable properties for inhaled administration. A proposed binding mode for 13f to the beta(2)-receptor is presented.

  DOI：

  10.1021/jm100326d

文献信息

• [EN] PHENETHANOLAMINE DERIVATIVES<br/>[FR] DERIVES DE LA PHENETHANOLAMINE
  申请人：GLAXO GROUP LTD

  公开号：WO2003091204A1

  公开（公告）日：2003-11-06

  The present invention relates to novel compounds of formula (I), or a salt, solvate, or physiologically functional derivative thereof, 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，或其盐、溶剂合物或生理功能衍生物，以及其制备方法，含有它们的药物组合物，以及它们在治疗中的应用，特别是在预防和治疗呼吸道疾病中的应用。
• Phenethanolamine derivatives
  申请人：Box Charles Philip

  公开号：US20050256201A1

  公开（公告）日：2005-11-17

  The present invention relates to novel compounds of formula (I), or a salt, solvate, or physiologically functional derivative thereof, 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.

  本发明与公式（I）的新化合物有关，或其盐，溶剂合物或生理功能衍生物，以及其制造过程，包含它们的制药组合物，并且它们在治疗中的使用，特别是在呼吸系统疾病的预防和治疗中的使用。
• Synthesis and Structure−Activity Relationships of Long-acting β₂ Adrenergic Receptor Agonists Incorporating Metabolic Inactivation: An Antedrug Approach
  作者：Panayiotis A. Procopiou、Victoria J. Barrett、Nicola J. Bevan、Keith Biggadike、Philip C. Box、Peter R. Butchers、Diane M. Coe、Richard Conroy、Amanda Emmons、Alison J. Ford、Duncan S. Holmes、Helen Horsley、Fern Kerr、Anne-Marie Li-Kwai-Cheung、Brian E. Looker、Inderjit S. Mann、Iain M. McLay、Valerie S. Morrison、Peter J. Mutch、Claire E. Smith、Paula Tomlin

  DOI：10.1021/jm100326d

  日期：2010.6.10

  A series of saligenin beta(2) adrenoceptor agonist antedrugs having high clearance were prepared by reacting a protected saligenin oxazolidinone with protected hydroxyethoxyalkoxyalkyl bromides, followed by removal of the hydroxy-protecting group, alkylation, and final deprotection. The compounds were screened for beta(2), beta(1), and beta(3) agonist activity in CHO cells. The onset and duration of action in vitro of selected compounds were assessed on isolated superfused guinea pig trachea. Compound 13f had high potency, selectivity, fast onset, and long duration of action in vitro and was found to have long duration in vivo, low oral bioavailability in the rat, and to be rapidly metabolized. Crystalline salts of 13f (vilanterol) were identified that had suitable properties for inhaled administration. A proposed binding mode for 13f to the beta(2)-receptor is presented.
• [EN] PHENETANOLAMINE DERIVATIVES<br/>[FR] DERIVES DE PHENETANOLAMINE
  申请人：GLAXO GROUP LTD

  公开号：WO2005044787A1

  公开（公告）日：2005-05-19

  Compounds of formula (I) and salts, solvates, and physiologically functional derivatives thereof, useful for the prophylaxis or treatment of a clinical condition for which a selective β2-adrenoreceptor agonist is indicated, for example asthma or chronic obstructive pulmonary disease (COPD).

  化合物的化学式(I)及其盐、溶剂合物和生理功能衍生物，可用于预防或治疗需要选择性β2-肾上腺素受体激动剂的临床病症，例如哮喘或慢性阻塞性肺疾病（COPD）。