2-bromo-1-(3-cyclopropylmethoxy-4-methoxyphenyl)ethanone | 1176406-07-7

• 英文名称: 2-bromo-1-(3-cyclopropylmethoxy-4-methoxyphenyl)ethanone
• 英文别名: 2-Bromo-1-[3-(cyclopropylmethoxy)-4-methoxyphenyl]ethanone
• CAS: 1176406-07-7
• 化学式: C₁₃H₁₅BrO₃
• 分子量: 299.164
• InChiKey: GZJWXXSAKWZSOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-bromo-1-(3-cyclopropylmethoxy-4-methoxyphenyl)ethanone 在 甲醇 、 sodium tetrahydroborate 作用下， 以 乙腈 为溶剂， 反应 51.0h， 生成 1-(2-(3-cyclopropylmethoxy-4-methoxyphenyl)-2-hydroxyethyl)-2-methylpyridin-4(1H)-one
  参考文献：
  名称：

  ANTI-INFLAMMATORY COMPOUND, AND PREPARATION AND USE THEREOF

  摘要：

  本发明提供一种抗炎化合物，该化合物具有如下所示的结构（I）： 该化合物是一个重要的自身免疫激活靶点，对PDE4具有强烈的抑制作用，易于渗透皮肤，并且是一种易于降解的新型抗炎化合物。

  公开号：

  US20200377460A1
• 作为产物：
  描述：

  1-(3-cyclopropylmethoxy-4-methoxyphenyl)ethanone 在 N-溴代丁二酰亚胺(NBS) 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以27%的产率得到2-bromo-1-(3-cyclopropylmethoxy-4-methoxyphenyl)ethanone
  参考文献：
  名称：

  ANTI-INFLAMMATORY COMPOUND, AND PREPARATION AND USE THEREOF

  摘要：

  本发明提供一种抗炎化合物，该化合物具有如下所示的结构（I）： 该化合物是一个重要的自身免疫激活靶点，对PDE4具有强烈的抑制作用，易于渗透皮肤，并且是一种易于降解的新型抗炎化合物。

  公开号：

  US20200377460A1

文献信息

• ANTI-INFLAMMATORY COMPOUND AND PREPARATION AND USE THEREOF
  申请人：Vivavision Biotech, Inc.

  公开号：EP3777979A1

  公开（公告）日：2021-02-17

  The present invention provides an anti-inflammatory compound, which is a compound having a structure (I) as shown below: The compound is a target that is important for autoimmune activation, and that has strong inhibitory effect on PDE4 and penetrates the skin easily, and is a new type anti-inflammatory compound that is easily degraded.

  本发明提供了一种抗炎化合物，它是一种具有如下所示结构（I）的化合物： 该化合物以自身免疫活化为重要靶点，对 PDE4 有较强的抑制作用，易渗透皮肤，是一种易降解的新型抗炎化合物。
• Exploration and optimization of substituted triazolothiadiazines and triazolopyridazines as PDE4 inhibitors
  作者：Amanda P. Skoumbourdis、Christopher A. LeClair、Eduard Stefan、Adrian G. Turjanski、William Maguire、Steven A. Titus、Ruili Huang、Douglas S. Auld、James Inglese、Christopher P. Austin、Stephen W. Michnick、Menghang Xia、Craig J. Thomas

  DOI：10.1016/j.bmcl.2009.01.057

  日期：2009.7

  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.