2-{(2R,4aR,5S,6S,7aS)-5-[(4-chloro-3-methylphenoxy)methyl]-6-hydroxyoctahydrocyclopenta[b]pyran-2-yl}-1,3-thiazole-4-carboxylic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-{(2R,4aR,5S,6S,7aS)-5-[(4-chloro-3-methylphenoxy)methyl]-6-hydroxyoctahydrocyclopenta[b]pyran-2-yl}-1,3-thiazole-4-carboxylic acid
• 英文别名: 2-[(2R,4aR,5S,6S,7aS)-5-[(4-chloro-3-methylphenoxy)methyl]-6-hydroxy-2,3,4,4a,5,6,7,7a-octahydrocyclopenta[b]pyran-2-yl]-1,3-thiazole-4-carboxylic acid
• 化学式: C₂₀H₂₂ClNO₅S
• 分子量: 423.917
• InChiKey: GZTLLBIEEIZFFD-GPYXMWEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  117
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  在 水 、 sodium hydroxide 作用下， 以 甲醇 、 乙二醇二甲醚 为溶剂， 以100%的产率得到2-{(2R,4aR,5S,6S,7aS)-5-[(4-chloro-3-methylphenoxy)methyl]-6-hydroxyoctahydrocyclopenta[b]pyran-2-yl}-1,3-thiazole-4-carboxylic acid
  参考文献：
  名称：

  Structural optimization and structure–functional selectivity relationship studies of G protein-biased EP2 receptor agonists

  摘要：

  The modification of the novel G protein-biased EP2 agonist 1 has been investigated to improve its G protein activity and develop a better understanding of its structure-functional selectivity relationship (SFSR). The optimization of the substituents on the phenyl ring of 1, followed by the inversion of the hydroxyl group on the cyclopentane moiety led to compound 9, which showed a 100-fold increase in its G protein activity compared with 1 without any increase in beta-arrestin recruitment. Furthermore, SFSR studies revealed that the combination of meta and para substituents on the phenyl moiety was crucial to the functional selectivity. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.03.110