5-(4-bromobenzyloxy)-4H-chromen-4-one | 1393374-53-2

• 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: 5-(4-bromobenzyloxy)-4H-chromen-4-one
• 英文别名: 5-[(4-Bromophenyl)methoxy]chromen-4-one
• CAS: 1393374-53-2
• 化学式: C₁₆H₁₁BrO₃
• 分子量: 331.166
• InChiKey: DCTUFQYGQXNTDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 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：

  2,6-二羟基苯乙酮 在 盐酸 、 水 、 sodium methylate 、 potassium carbonate 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 12.5h， 生成 5-(4-bromobenzyloxy)-4H-chromen-4-one
  参考文献：
  名称：

  Selected chromone derivatives as inhibitors of monoamine oxidase

  摘要：

  A previous study has shown that a series of C6-benzyloxy substituted chromones exhibit high binding affinities for human monoamine oxidase (MAO) B. In an attempt to discover additional chromones with potent and selective MAO-B inhibitory potencies and to further examine the structure-activity relationships of MAO-B inhibition by chromones, the series was expanded with homologues containing polar functional groups on C3 of the chromone ring. The results demonstrate that 6-[(3-bromobenzyl)oxy] chromones containing acidic and aldehydic functional groups on C3 act as potent reversible MAO-B inhibitors with IC50 values of 2.8 and 3.7 nM, respectively. Interestingly, a 2-hydroxy-2,3-dihydro-1-benzopyran-4-one derivative as well as open-ring 2-acetylphenol analogues of the chromones also were potent MAO-B inhibitors with IC50 values ranging from 4 to 11 nM. Chromone derivatives containing the benzyloxy substituent on C5 of the chromone ring, however, exhibit MAO-B inhibition potencies that are several orders of magnitude weaker. High potency inhibitors of MAO-B may find application in the therapy of neurodegenerative disorders such as Parkinson's disease. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.025

文献信息

• Selected chromone derivatives as inhibitors of monoamine oxidase
  作者：Lesetja J. Legoabe、Anél Petzer、Jacobus P. Petzer

  DOI：10.1016/j.bmcl.2012.07.025

  日期：2012.9

  A previous study has shown that a series of C6-benzyloxy substituted chromones exhibit high binding affinities for human monoamine oxidase (MAO) B. In an attempt to discover additional chromones with potent and selective MAO-B inhibitory potencies and to further examine the structure-activity relationships of MAO-B inhibition by chromones, the series was expanded with homologues containing polar functional groups on C3 of the chromone ring. The results demonstrate that 6-[(3-bromobenzyl)oxy] chromones containing acidic and aldehydic functional groups on C3 act as potent reversible MAO-B inhibitors with IC50 values of 2.8 and 3.7 nM, respectively. Interestingly, a 2-hydroxy-2,3-dihydro-1-benzopyran-4-one derivative as well as open-ring 2-acetylphenol analogues of the chromones also were potent MAO-B inhibitors with IC50 values ranging from 4 to 11 nM. Chromone derivatives containing the benzyloxy substituent on C5 of the chromone ring, however, exhibit MAO-B inhibition potencies that are several orders of magnitude weaker. High potency inhibitors of MAO-B may find application in the therapy of neurodegenerative disorders such as Parkinson's disease. (C) 2012 Elsevier Ltd. All rights reserved.