6-[(4-bromobenzyl)oxy]-4H-chromen-4-one | 1361926-65-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-[(4-bromobenzyl)oxy]-4H-chromen-4-one
• 英文别名: 6-[(4-Bromophenyl)methoxy]chromen-4-one
• CAS: 1361926-65-9
• 化学式: C₁₆H₁₁BrO₃
• 分子量: 331.166
• InChiKey: KQZUFMSIIAMVMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-hydroxy-4H-chromen-4-one 、 对溴溴苄 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以21%的产率得到6-[(4-bromobenzyl)oxy]-4H-chromen-4-one
  参考文献：
  名称：

  Inhibition of monoamine oxidase by selected C6-substituted chromone derivatives

  摘要：

  Chromone has been reported to be a useful scaffold for the design of monoamine oxidase (MAO) inhibitors. In an attempt to discover highly potent MAO inhibitors and to contribute to the known structure-activity relationships (SAR) of MAO inhibition by chromones, in the present study, we have synthesized a series of chromone derivatives substituted at C6 with a variety of alkyloxy substituents, and evaluated the resulting compounds as inhibitors of recombinant human MAO-A and -B. The results document that the C6-substituted chromones are potent reversible MAO-B inhibitors with IC50 values in the low nM range (2-76 nM). The chromones were also found to bind reversibly to MAO-A, but with lower affinities compared to MAO-B. It may therefore be concluded that C6-substituted chromones are highly potent MAO-B selective inhibitors and promising lead compounds for the development of therapy for neurodegenerative disorders such as Parkinson's disease. The results of this study are discussed with reference to possible binding orientations of a selected C6-substituted chromone in the active site cavities of MAO-A and -B. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.01.037

文献信息

• Inhibition of monoamine oxidase by selected C6-substituted chromone derivatives
  作者：Lesetja J. Legoabe、Anél Petzer、Jacobus P. Petzer

  DOI：10.1016/j.ejmech.2012.01.037

  日期：2012.3

  Chromone has been reported to be a useful scaffold for the design of monoamine oxidase (MAO) inhibitors. In an attempt to discover highly potent MAO inhibitors and to contribute to the known structure-activity relationships (SAR) of MAO inhibition by chromones, in the present study, we have synthesized a series of chromone derivatives substituted at C6 with a variety of alkyloxy substituents, and evaluated the resulting compounds as inhibitors of recombinant human MAO-A and -B. The results document that the C6-substituted chromones are potent reversible MAO-B inhibitors with IC50 values in the low nM range (2-76 nM). The chromones were also found to bind reversibly to MAO-A, but with lower affinities compared to MAO-B. It may therefore be concluded that C6-substituted chromones are highly potent MAO-B selective inhibitors and promising lead compounds for the development of therapy for neurodegenerative disorders such as Parkinson's disease. The results of this study are discussed with reference to possible binding orientations of a selected C6-substituted chromone in the active site cavities of MAO-A and -B. (C) 2012 Elsevier Masson SAS. All rights reserved.