(R)-2-bromo-1-(4-methoxy-3-((tetrahydrofuran-3-yl)oxy)phenyl)ethan-1-one | 1176406-09-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-2-bromo-1-(4-methoxy-3-((tetrahydrofuran-3-yl)oxy)phenyl)ethan-1-one
• CAS: 1176406-09-9
• 化学式: C₁₃H₁₅BrO₄
• 分子量: 315.164
• InChiKey: WFYSPLSNEVTSOJ-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.44
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-氨基-3-疏基-5-(2-氯苯基)-[1,2,4-]噻唑 、 (R)-2-bromo-1-(4-methoxy-3-((tetrahydrofuran-3-yl)oxy)phenyl)ethan-1-one 以 乙醇 为溶剂， 反应 4.0h， 生成 (R)-3-(2-chlorophenyl)-6-(4-methoxy-3-(tetrahydrofuran-3-yloxy)phenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine
  参考文献：
  名称：

  Exploration and optimization of substituted triazolothiadiazines and triazolopyridazines as PDE4 inhibitors

  摘要：

  An expansion of structure-activity studies on a series of substituted 7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine PDE4 inhibitors and the introduction of a related [1,2,4]triazolo[4,3-b]pyridazine based inhibitor of PDE4 is presented. The development of SAR included strategic incorporation of known substituents on the critical catachol diether moiety of the 6-phenyl appendage on each heterocyclic core. From these studies, (R)-3-(2,5-dimethoxyphenyl)-6-(4-methoxy-3-(tetrahydrofuran-3-yloxy)phenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine (10) and (R)-3-(2,5-dimethoxyphenyl)-6-(4-methoxy-3-(tetrahydrofuran-3-yloxy)phenyl)-[1,2,4]triazolo[4,3-b]pyridazine (18) were identified as highly potent PDE4A inhibitors. Each of these analogues was submitted across a panel of 21 PDE family members and was shown to be highly selective for PDE4 isoforms (PDE4A, PDE4B, PDE4C, PDE4D). Both 10 and 18 were then evaluated in divergent cell-based assays to assess their relevant use as probes of PDE4 activity. Finally, docking studies with selective ligands (including 10 and 18) were undertaken to better understand this chemotypes ability to bind and inhibit PDE4 selectively. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2009.01.057
• 作为产物：
  描述：

  1-[4-methoxy-3-[(3R)-tetrahydrofuranyloxy]phenyl]ethanone 在 溴 作用下， 以 氯仿 为溶剂， 生成 (R)-2-bromo-1-(4-methoxy-3-((tetrahydrofuran-3-yl)oxy)phenyl)ethan-1-one
  参考文献：
  名称：

  Exploration and optimization of substituted triazolothiadiazines and triazolopyridazines as PDE4 inhibitors

  摘要：

  An expansion of structure-activity studies on a series of substituted 7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine PDE4 inhibitors and the introduction of a related [1,2,4]triazolo[4,3-b]pyridazine based inhibitor of PDE4 is presented. The development of SAR included strategic incorporation of known substituents on the critical catachol diether moiety of the 6-phenyl appendage on each heterocyclic core. From these studies, (R)-3-(2,5-dimethoxyphenyl)-6-(4-methoxy-3-(tetrahydrofuran-3-yloxy)phenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine (10) and (R)-3-(2,5-dimethoxyphenyl)-6-(4-methoxy-3-(tetrahydrofuran-3-yloxy)phenyl)-[1,2,4]triazolo[4,3-b]pyridazine (18) were identified as highly potent PDE4A inhibitors. Each of these analogues was submitted across a panel of 21 PDE family members and was shown to be highly selective for PDE4 isoforms (PDE4A, PDE4B, PDE4C, PDE4D). Both 10 and 18 were then evaluated in divergent cell-based assays to assess their relevant use as probes of PDE4 activity. Finally, docking studies with selective ligands (including 10 and 18) were undertaken to better understand this chemotypes ability to bind and inhibit PDE4 selectively. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2009.01.057