8-(chloromethyl)-5-methoxypsoralen

• 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: 8-(chloromethyl)-5-methoxypsoralen
• 英文别名: 9-(Chloromethyl)-4-methoxyfuro[3,2-g]chromen-7-one
• 化学式: C₁₃H₉ClO₄
• 分子量: 264.665
• InChiKey: OHAUUIVTZFAWFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲醇 、 8-(chloromethyl)-5-methoxypsoralen 反应 6.0h， 以63%的产率得到4-Methoxy-9-methoxymethyl-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
• 作为产物：
  描述：

  佛手苷内酯 、 氯甲基甲基醚 在 溶剂黄146 作用下， 生成 8-(chloromethyl)-5-methoxypsoralen
  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

• Psoralens for pathogen inactivation
  申请人：Cerus Corporation

  公开号：US20030082510A1

  公开（公告）日：2003-05-01

  Psoralen compound compositions are synthesized which have primaryamino substitutions on the 3-, 4-, 5-, and 8-positions of the psoralen, which yet permit their binding to nucleic acid of pathogens. Reaction conditions that photoactivate these psoralens result in the inactivation of pathogens which contain nucleic acid. The compounds show similar activity in test systems to 4′ and 5′ derivatives of psoralen useful for inactivation of pathogens in blood products. In addition to the psoralen compositions, the invention contemplates such inactivating methods using the new psoralens.

  合成了一种含有3-、4-、5-和8-位置的主要氨基取代基的芳香光毒素化合物组合物，但仍允许它们与病原体的核酸结合。光活化这些芳香光毒素的反应条件导致含有核酸的病原体失活。这些化合物在测试系统中显示出与用于血液制品中病原体失活的4'和5'衍生物的类似活性。除了芳香光毒素组合物外，本发明还考虑使用新的芳香光毒素进行失活方法。
• EP1032265A4
  申请人：——

  公开号：EP1032265A4

  公开（公告）日：2001-05-30
• NEW PSORALENS FOR PATHOGEN INACTIVATION
  申请人：Cerus Corporation

  公开号：EP1032265B1

  公开（公告）日：2003-10-29
• US6133460A
  申请人：——

  公开号：US6133460A

  公开（公告）日：2000-10-17
• US6455286B1
  申请人：——

  公开号：US6455286B1

  公开（公告）日：2002-09-24