3-methyl-2,3-dihydro-furo[3,2-g]chromen-7-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-methyl-2,3-dihydro-furo[3,2-g]chromen-7-one
• 英文别名: 3-Methyl-2,3-dihydro-furo[3,2-g]chromen-7-on；3-Methyl-2,3-dihydrofuro[3,2-g]chromen-7-one
• 化学式: C₁₂H₁₀O₃
• 分子量: 202.21
• InChiKey: YYABNLNVASVPDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  7-羟基香豆素 在 palladium on activated charcoal 氢氧化钾 、 potassium carbonate 、 环己烯 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 66.0h， 生成 3-methyl-2,3-dihydro-furo[3,2-g]chromen-7-one
  参考文献：
  名称：

  Alkoxypsoralens, Novel Nonpeptide Blockers of Shaker-Type K⁺ Channels:  Synthesis and Photoreactivity

  摘要：

  A series of psoralens and structurally related 5,7-disubstituted coumarins was synthesized and investigated for their K+ channel blocking activity as well as for their phototoxicity to Artemia salina and their ability to generate singlet oxygen and to photomodify DNA. After screening the compounds on Ranvier nodes of the toad Xenopus Laevis, the affinities of the most promising compounds, which proved to be psoralens bearing alkoxy substituents in the 5-position or alkoxymethyl substituents in the neighboring 4- or 4'-position, to a number of homomeric K+ channels were characterized. All compounds exhibited the highest affinity to Kv1.2. 5,8-Diethoxypsoralen (10d) was found to be an equally potent inhibitor of Kv1.2 and Kv1.3, while lacking the phototoxicity normally inherent in psoralens. The reported compounds represent a novel series of nonpeptide blockers of Shaker-type K+ channels that could be further developed into selective inhibitors of Kv1.2 or Kv1.3.

  DOI：

  10.1021/jm981032o

文献信息

• Foster et al., Journal of the Chemical Society, 1948, p. 2254,2258
  作者：Foster et al.

  DOI：——

  日期：——
• Alkoxypsoralens, Novel Nonpeptide Blockers of <i>Shaker</i>-Type K⁺ Channels:  Synthesis and Photoreactivity
  作者：Heike Wulff、Heiko Rauer、Tim Düring、Christine Hanselmann、Katharina Ruff、Anja Wrisch、Stephan Grissmer、Wolfram Hänsel

  DOI：10.1021/jm981032o

  日期：1998.11.1

  A series of psoralens and structurally related 5,7-disubstituted coumarins was synthesized and investigated for their K+ channel blocking activity as well as for their phototoxicity to Artemia salina and their ability to generate singlet oxygen and to photomodify DNA. After screening the compounds on Ranvier nodes of the toad Xenopus Laevis, the affinities of the most promising compounds, which proved to be psoralens bearing alkoxy substituents in the 5-position or alkoxymethyl substituents in the neighboring 4- or 4'-position, to a number of homomeric K+ channels were characterized. All compounds exhibited the highest affinity to Kv1.2. 5,8-Diethoxypsoralen (10d) was found to be an equally potent inhibitor of Kv1.2 and Kv1.3, while lacking the phototoxicity normally inherent in psoralens. The reported compounds represent a novel series of nonpeptide blockers of Shaker-type K+ channels that could be further developed into selective inhibitors of Kv1.2 or Kv1.3.