ethyl 3-[(3-bromophenyl)thio]propanoate | 855997-35-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: ethyl 3-[(3-bromophenyl)thio]propanoate
• 英文别名: ethyl 3-(3-bromophenyl)sulfanylpropanoate
• CAS: 855997-35-2
• 化学式: C₁₁H₁₃BrO₂S
• 分子量: 289.193
• InChiKey: NZRJITAIZUXYJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3-[(3-bromophenyl)thio]propanoate 在 硫酸 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 111.0h， 生成 7-溴硫代苯并二氢吡喃-4-酮
  参考文献：
  名称：

  Discovery of a Rapidly Metabolized, Long-Acting β₂ Adrenergic Receptor Agonist with a Short Onset Time Incorporating a Sulfone Group Suitable for Once-Daily Dosing

  摘要：

  A series of novel, potent, and selective human beta(2) adrenoceptor agonists incorporating a sulfone moiety on the terminal right-hand-side phenyl ring of (R)-salmeterol is presented. Sulfone 10b had salmeterol-like potency and selectivity profile, long duration of action on guinea pig trachea, and longer than salmeterol duration of action in vivo, suitable for once-daily dosing. It had lower than salmeterol oral absorption in rat, lower bioavailability in rat and dog, and a high turnover in human hepatocytes. It was metabolized in human hepatocytes by hydroxylation, oxidation, cleavage, and conjugation; most of the metabolites would be expected to have reduced or no beta(2) activity. The 4-biphenylsulfonic acid was identified as a crystalline, non-hygroscopic salt of 10b, suitable for inhaled delivery. Furthermore, it was free of any genetic toxicity issues and was considered as a backup to vilanterol.

  DOI：

  10.1021/jm401532g
• 作为产物：
  描述：

  3-巯基丙酸乙酯 、 1-溴-3-碘苯 在 1,1'-双(二苯基膦)二茂铁 、 (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one;palladium 氮气 、 盐酸 、 Brine 、 magnesium sulfate 、 cyclohexane, methylene chloride 作用下， 以 N,N-二甲基甲酰胺 、 三乙胺 、 乙酸乙酯 为溶剂， 反应 1.67h， 以to give the title compound (1.58 g) LCMS RT=3.50 min的产率得到ethyl 3-[(3-bromophenyl)thio]propanoate
  参考文献：
  名称：

  Benzothiophen and thiochrone containing phenethanolamine derivatives for the treatment of respiratory disorders

  摘要：

  化合物的公式(I)及其盐类、溶剂化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：

  US07294650B2

文献信息

• [EN] BENZOTHIOPHENE-AND BENZOTHIOCHROMENE-COMPRISING DERIVATIVES OF PHENETHANOLAMINE FOR THE TREATMENT<br/>[FR] BENZOTHIOPHENE- ET BENZOTHIOCHROMENE- COMPRENANT DES DERIVES DE PHENETHANOLAMINE POUR TRAITEMENTS
  申请人：GLAXO GROUP LTD

  公开号：WO2005058867A1

  公开（公告）日：2005-06-30

  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).

  公式（I）的化合物和其盐，溶剂合物以及生理学功能衍生物，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）。
• Benzothiophen and thiochrone containing phenethanolamine derivatives for the treatment of respiratory disorders
  申请人：Biggadike Keith

  公开号：US20070172385A1

  公开（公告）日：2007-07-26

  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 β 2 -adrenoreceptor agonist is indicated, for example asthma or chronic obstructive pulmonary disease (COPD).

  公式(I)的化合物及其盐、溶剂合物和生理功能衍生物，可用于预防或治疗选择性β2-肾上腺素能受体激动剂适用的临床疾病，例如哮喘或慢性阻塞性肺疾病（COPD）。
• BENZOTHIOPHENE- AND THIOCHROMENE CONTAINING PHENETHANOLAMINE DERIVATIVES FOR THE TREATMENT OF RESPIRATORY DISORDERS
  申请人：GLAXO GROUP LIMITED

  公开号：EP1730133A1

  公开（公告）日：2006-12-13
• US7294650B2
  申请人：——

  公开号：US7294650B2

  公开（公告）日：2007-11-13
• Discovery of a Rapidly Metabolized, Long-Acting β₂ Adrenergic Receptor Agonist with a Short Onset Time Incorporating a Sulfone Group Suitable for Once-Daily Dosing
  作者：Panayiotis A. Procopiou、Victoria J. Barrett、Keith Biggadike、Peter R. Butchers、Andrew Craven、Alison J. Ford、Stephen B. Guntrip、Duncan S. Holmes、Sara C. Hughes、Anne E. Jones、Brian E. Looker、Peter J. Mutch、Mark Ruston、Deborah Needham、Claire E. Smith

  DOI：10.1021/jm401532g

  日期：2014.1.9

  A series of novel, potent, and selective human beta(2) adrenoceptor agonists incorporating a sulfone moiety on the terminal right-hand-side phenyl ring of (R)-salmeterol is presented. Sulfone 10b had salmeterol-like potency and selectivity profile, long duration of action on guinea pig trachea, and longer than salmeterol duration of action in vivo, suitable for once-daily dosing. It had lower than salmeterol oral absorption in rat, lower bioavailability in rat and dog, and a high turnover in human hepatocytes. It was metabolized in human hepatocytes by hydroxylation, oxidation, cleavage, and conjugation; most of the metabolites would be expected to have reduced or no beta(2) activity. The 4-biphenylsulfonic acid was identified as a crystalline, non-hygroscopic salt of 10b, suitable for inhaled delivery. Furthermore, it was free of any genetic toxicity issues and was considered as a backup to vilanterol.