5,7-Diethoxy-chromen-2-one | 215865-89-7

• 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: 5,7-Diethoxy-chromen-2-one
• 英文别名: 5,7-diethoxychromen-2-one
• CAS: 215865-89-7
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: WDSDYZVMKWWVIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  一氯丙酮 、 5,7-Diethoxy-chromen-2-one 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 6.0h， 以82%的产率得到5,7-bis(2-oxopropoxy)coumarin
  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
• 作为产物：
  描述：

  间苯三酚 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 、 zinc(II) chloride 作用下， 以 1,4-二氧六环 、 丙酮 为溶剂， 反应 30.0h， 生成 5,7-Diethoxy-chromen-2-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

• Co-initiator compositions for photopolymerization containing 3-acyl-substituted coumarins, photopolymerizable composition and photographic element
  申请人：EASTMAN KODAK COMPANY (a New Jersey corporation)

  公开号：EP0022188B1

  公开（公告）日：1984-10-03
• Sensitized photopolymerizable compositions and use thereof in lithographic printing plates
  申请人：Kodak Polychrome Graphics LLC

  公开号：EP0730201B1

  公开（公告）日：2001-05-09
• METHOD FOR PRODUCING POLYDIENES AND POLYDIENE COPOLYMERS WITH REDUCED COLD FLOW
  申请人：Bridgestone Corporation

  公开号：US20140187725A1

  公开（公告）日：2014-07-03

  A method for preparing a coupled polymer, the method comprising the steps of: (i) polymerizing monomer to form a reactive polymer, and (ii) reacting the reactive polymer with coumarin or a substituted coumarin compound.
• US9127092B2
  申请人：——

  公开号：US9127092B2

  公开（公告）日：2015-09-08
• 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.