1-[4-methoxy-3-[(3R)-tetrahydrofuranyloxy]phenyl]ethanone | 784190-01-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[4-methoxy-3-[(3R)-tetrahydrofuranyloxy]phenyl]ethanone
• 英文别名: 1-(4-methoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-ethanone；1-[4-methoxy-3-(3R)-tetrahydrofuranyloxyphenyl]ethanone；1-[4-methoxy-3-[(3R)-oxolan-3-yl]oxyphenyl]ethanone
• CAS: 784190-01-8
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: RUKOULJOAKXVNV-LLVKDONJSA-N

物化性质

• 沸点：
  372.0±42.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  1-(4-methoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-ethanol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以83%的产率得到1-[4-methoxy-3-[(3R)-tetrahydrofuranyloxy]phenyl]ethanone
  参考文献：
  名称：

  Phosphodiesterase 4 inhibitors

  摘要：

  选择性PDE4抑制是通过芳基和杂环基吡唑化合物实现的。与罗利普兰（rolipram）等化合物相比，这些化合物表现出更好的PDE4抑制作用，并且在抑制其他类PDE时表现出选择性。

  公开号：

  US20070254913A1

文献信息

• [EN] PYRAZOLE DERIVATIVES AS PHOSPHODIESTERASE 4 INHIBITORS<br/>[FR] DERIVES DU PYRAZOLE INHIBITEURS DE LA PHOSPHODIESTERASE 4
  申请人：MEMORY PHARM CORP

  公开号：WO2004094411A1

  公开（公告）日：2004-11-04

  Selective PDE4 inhibition is achieved by aryl and heteroaryl pyrazole compounds. The compounds exhibit improved PDE4 inhibition as compared to compounds such as rolipram and show selectivity with regard to inhibition of other classes of PDEs.

  通过芳基和杂环芳基吡唑化合物实现选择性PDE4抑制。与罗利普兰等化合物相比，这些化合物表现出更好的PDE4抑制作用，并且在抑制其他类PDEs方面表现出选择性。
• PHOSPHODIESTERASE 4 INHIBITORS
  申请人：Hopper Allen

  公开号：US20090221661A1

  公开（公告）日：2009-09-03

  Selective PDE4 inhibition is achieved by aryl and heteroaryl pyrazole compounds. The compounds exhibit improved PDE4 inhibition as compared to compounds such as rolipram and show selectivity with regard to inhibition of other classes of PDEs.

  选择性PDE4抑制是由芳基和杂环基吡唑化合物实现的。与如Rolipram等化合物相比，这些化合物表现出更好的PDE4抑制作用，并且在抑制其他类别的PDE方面表现出选择性。
• WO2006/44528
  申请人：——

  公开号：——

  公开（公告）日：——
• US7226930B2
  申请人：——

  公开号：US7226930B2

  公开（公告）日：2007-06-05
• US7432266B2
  申请人：——

  公开号：US7432266B2

  公开（公告）日：2008-10-07