8-bromo-6-((4-(methylsulfonyl)phenoxy)methyl)quinoline | 1252807-77-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 8-bromo-6-((4-(methylsulfonyl)phenoxy)methyl)quinoline
• CAS: 1252807-77-4
• 化学式: C₁₇H₁₄BrNO₃S
• 分子量: 392.273
• InChiKey: YLIUYSYULLLONW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  56.26
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(3-(二氟甲氧基)苯基)-4,4,5,5-四甲基-1,3,2-二氧硼戊环 、 8-bromo-6-((4-(methylsulfonyl)phenoxy)methyl)quinoline 在 Pd(dppf)Cl₂ 、 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 8-(3-(Difluoromethoxy)phenyl)-6-((4-(methylsulfonyl)phenoxy)methyl)quinoline
  参考文献：
  名称：

  The discovery and synthesis of highly potent subtype selective phosphodiesterase 4D inhibitors

  摘要：

  The SAR study of a series of 6-aryloxymethyl-8-aryl substituted quinolines is described. Optimization of the series led to the discovery of compound 26b, a highly potent (IC(50) = 0.6 nM) and selective PDE4D inhibitor with a 75-fold selectivity over the A, B, and C subtypes and over 18,000-fold selectivity against other PDE family members. Rat pharmacokinetics and tissue distribution are also summarized. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.07.076
• 作为产物：
  描述：

  4-甲基磺酰苯酚 、 8-溴-6-(溴甲基)喹啉 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 8-bromo-6-((4-(methylsulfonyl)phenoxy)methyl)quinoline
  参考文献：
  名称：

  The discovery and synthesis of highly potent subtype selective phosphodiesterase 4D inhibitors

  摘要：

  The SAR study of a series of 6-aryloxymethyl-8-aryl substituted quinolines is described. Optimization of the series led to the discovery of compound 26b, a highly potent (IC(50) = 0.6 nM) and selective PDE4D inhibitor with a 75-fold selectivity over the A, B, and C subtypes and over 18,000-fold selectivity against other PDE family members. Rat pharmacokinetics and tissue distribution are also summarized. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.07.076