4-hydroxy-7-((R)-1-hydroxy-2-((R)-1-(naphthalen-2-yl)ethylamino)ethyl)benzo[d]thiazol-2(3H)-one | 663925-16-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-hydroxy-7-((R)-1-hydroxy-2-((R)-1-(naphthalen-2-yl)ethylamino)ethyl)benzo[d]thiazol-2(3H)-one
• 英文别名: 4-hydroxy-7-[(1R)-1-hydroxy-2-[[(1R)-1-naphthalen-2-ylethyl]amino]ethyl]-3H-1,3-benzothiazol-2-one
• CAS: 663925-16-4
• 化学式: C₂₁H₂₀N₂O₃S
• 分子量: 380.467
• InChiKey: MKYUDVKGSDGIOZ-XIKOKIGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 甲酸 作用下， 反应 24.0h， 生成 4-hydroxy-7-((R)-1-hydroxy-2-((R)-1-(naphthalen-2-yl)ethylamino)ethyl)benzo[d]thiazol-2(3H)-one
  参考文献：
  名称：

  A physical properties based approach for the exploration of a 4-hydroxybenzothiazolone series of β2-adrenoceptor agonists as inhaled long-acting bronchodilators

  摘要：

  The chiral synthesis of a 4-hydroxybenzothiazolone based series of beta(2)-adrenoceptor agonists is described. Using this methodology a library of N-substituted analogues were prepared for the rapid identification of leads with the potential to be fast onset and long-acting inhaled bronchodilators with improved therapeutic margins. The design of the library to achieve the targeted profile was based upon lipophilicity and metabolism based hypotheses. This approach identified beta-phenethyl, alpha-substituted cyclopentyl and monoterpene N-substituents to be of particular interest for further evaluation, as exemplified by structures 19, 29 and 33, respectively. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.06.136

文献信息

• A physical properties based approach for the exploration of a 4-hydroxybenzothiazolone series of β2-adrenoceptor agonists as inhaled long-acting bronchodilators
  作者：David Beattie、Michelle Bradley、Andrew Brearley、Steven J. Charlton、Bernard M. Cuenoud、Robin A. Fairhurst、Peter Gedeck、Martin Gosling、Diana Janus、Darryl Jones、Christine Lewis、Clive McCarthy、Helen Oakman、Rowan Stringer、Roger J. Taylor、Andrew Tuffnell

  DOI：10.1016/j.bmcl.2010.06.136

  日期：2010.9

  The chiral synthesis of a 4-hydroxybenzothiazolone based series of beta(2)-adrenoceptor agonists is described. Using this methodology a library of N-substituted analogues were prepared for the rapid identification of leads with the potential to be fast onset and long-acting inhaled bronchodilators with improved therapeutic margins. The design of the library to achieve the targeted profile was based upon lipophilicity and metabolism based hypotheses. This approach identified beta-phenethyl, alpha-substituted cyclopentyl and monoterpene N-substituents to be of particular interest for further evaluation, as exemplified by structures 19, 29 and 33, respectively. (C) 2010 Elsevier Ltd. All rights reserved.