(1S)-1-(3-amino-4-benzyloxyphenyl)-2-bromoethan-1-ol | 1122063-33-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (1S)-1-(3-amino-4-benzyloxyphenyl)-2-bromoethan-1-ol
• 英文别名: (1S)-1-(3-amino-4-phenylmethoxyphenyl)-2-bromoethanol
• CAS: 1122063-33-5
• 化学式: C₁₅H₁₆BrNO₂
• 分子量: 322.202
• InChiKey: AOKALCBWBYJIDM-CQSZACIVSA-N

物化性质

• 沸点：
  478.5±45.0 °C(Predicted)
• 密度：
  1.460±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S)-1-(3-amino-4-benzyloxyphenyl)-2-bromoethan-1-ol 在 乙酸酐 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 7.0h， 生成 N-(5-(2-(benzyl(2-(4-(3,4-dimethoxyphenyl)-1-oxo-4a,5,6,7,8,8a-hexahydrophthalazin-2(1H)-yl)butyl)amino)-1-hydroxyethyl)-2-(benzyloxy)phenyl)formamide
  参考文献：
  名称：

  Dual β2-adrenoceptor agonists-PDE4 inhibitors for the treatment of asthma and COPD

  摘要：

  We designed and synthesized a novel class of dual pharmacology bronchodilators targeting both beta 2-adrenoceptor and PDE4 by applying a multivalent approach. The most potent dual pharmacology molecule, compound 29, possessed good inhibitory activity on PDE4B2 (IC50 = 0.278 mu M, which was more potent than phthalazinone, IC50 = 0.520 mu M) and possessed excellent relaxant effects on tracheal rings precontracted by histamine (pEC(50) = 9.3). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.013
• 作为产物：
  描述：

  4-苄氧基-3-硝基苯乙酮 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 二甲基硫 、 platinum on carbon 、 氢气 、 溴 、 sodium formate 作用下， 以 四氢呋喃 、 水 、 溶剂黄146 为溶剂， 20.0~40.0 ℃ 、3.45 MPa 条件下， 反应 14.0h， 生成 (1S)-1-(3-amino-4-benzyloxyphenyl)-2-bromoethan-1-ol
  参考文献：
  名称：

  Dual β2-adrenoceptor agonists-PDE4 inhibitors for the treatment of asthma and COPD

  摘要：

  We designed and synthesized a novel class of dual pharmacology bronchodilators targeting both beta 2-adrenoceptor and PDE4 by applying a multivalent approach. The most potent dual pharmacology molecule, compound 29, possessed good inhibitory activity on PDE4B2 (IC50 = 0.278 mu M, which was more potent than phthalazinone, IC50 = 0.520 mu M) and possessed excellent relaxant effects on tracheal rings precontracted by histamine (pEC(50) = 9.3). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.013

文献信息

• Acetamide Stereoisomer
  申请人：Abolin Craig R.

  公开号：US20090060922A1

  公开（公告）日：2009-03-05

  The compound of formula (I) is a water-stable, long acting β 2 -selective adrenoceptor agonist useful as a bronchodilator in the treatment of bronchoconstriction associated with reversible obstructive airways diseases and the like.

  化学式（I）的化合物是一种水稳定的、长效的β2选择性肾上腺素受体激动剂，可用作支气管扩张剂，用于治疗与可逆性阻塞性气道疾病等相关的支气管痉挛。
• Carbamate Stereoisomer
  申请人：Abolin Craig R.

  公开号：US20090060917A1

  公开（公告）日：2009-03-05

  The compound of formula (I) is a water-stable, long acting β 2 -selective adrenoceptor agonist useful as a bronchodilator in the treatment of bronchoconstriction associated with reversible obstructive airways diseases and the like.

  化学式（I）的化合物是一种稳定性好、长效的β2选择性肾上腺素受体激动剂，可用作治疗与可逆性阻塞性气道疾病相关的支气管痉挛的支气管扩张剂。
• Carbamate stereoisomer
  申请人：Sunovion Pharmaceuticals Inc.

  公开号：US08173829B2

  公开（公告）日：2012-05-08

  The compound of formula (I) is a water-stable, long acting β2-selective adrenoceptor agonist useful as a bronchodilator in the treatment of bronchoconstriction associated with reversible obstructive airways diseases and the like.

  化合物式(I)的化合物是一种水稳定、长效的β2选择性肾上腺素受体激动剂，可用作支气管扩张剂，治疗与可逆性阻塞性气道疾病等相关的支气管收缩。
• Acetamide stereoisomer
  申请人：Sunovion Pharmaceuticals Inc.

  公开号：US08664441B2

  公开（公告）日：2014-03-04

  The compound of formula (I) is a water-stable, long acting β2-selective adrenoceptor agonist useful as a bronchodilator in the treatment of bronchoconstriction associated with reversible obstructive airways diseases and the like. Processes for making the compound of formula (I), as well as related intermediates, are disclosed.

  化合物式(I)是一种水稳定的、长效的β2选择性肾上腺素受体激动剂，适用于治疗与可逆性阻塞性气道疾病等相关的支气管收缩，具有支气管扩张作用。本文揭示了制备化合物式(I)及其相关中间体的方法。
• ACETAMIDE STEREOISOMER
  申请人：SUNOVION PHARMACEUTICALS INC.

  公开号：US20150225334A1

  公开（公告）日：2015-08-13

  The compound of formula (I) is a water-stable, long acting β 2 -selective adrenoceptor agonist useful as a bronchodilator in the treatment of bronchoconstriction associated with reversible obstructive airways diseases and the like. Processes for making the compound of formula (I), as well as related intermediates, are disclosed.

  式(I)的化合物是一种水稳定的长效β2选择性肾上腺素受体激动剂，可用作支气管扩张剂，用于治疗可逆性阻塞性气道疾病等引起的支气管收缩。公开了制备式(I)化合物及相关中间体的方法。