5-[(triethylammonio)methyl]-8-methoxypsoralen chloride | 96616-41-0

• 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-[(triethylammonio)methyl]-8-methoxypsoralen chloride
• 英文别名: N,N,N-Triethyl-9-methoxy-7-oxo-7H-furo(3,2-g)(1)benzopyran-4-methanaminium chloride；triethyl-[(9-methoxy-7-oxofuro[3,2-g]chromen-4-yl)methyl]azanium;chloride
• CAS: 96616-41-0
• 化学式: C₁₉H₂₄NO₄*Cl
• 分子量: 365.857
• InChiKey: BAMFJGIOJAXVBP-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.93
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  8-甲氧基补骨脂素 在 溶剂黄146 作用下， 反应 6.0h， 生成 5-[(triethylammonio)methyl]-8-methoxypsoralen chloride
  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

• Psoralenamines. 3. Synthesis, pharmacological behavior, and DNA binding of 5-(aminomethyl)-8-methoxy-, 5-[[(3-aminopropyl)oxy]methyl]- and 8-[(3-aminopropyl)oxy]psoralen derivatives
  作者：John B. Hansen、Peter Bjerring、Ole Buchardt、Peter Ebbesen、Anders Kanstrup、Gunnar Karup、Peter H. Knudsen、Peter E. Nielsen、Bengt Norden、Birgitta Ygge

  DOI：10.1021/jm00146a006

  日期：1985.8

  that only the 8-substituted psoralens bind to DNA by intercalation. Furthermore, the ability to photoinduce interstrand cross-links in calf thymus DNA, in vitro, was as efficient as that of 8-methoxypsoralen for the 8-substituted psoralens, which were up to 25 times as efficient as the 5-substituted psoralens. Four of the psoralens studied were radiolabeled and used to study photobinding to DNA. Analogously

  5-（氨基甲基）-8-甲氧基补骨脂素，8-[[（3-氨基丙基）氧基]补骨脂素和5-[[[[3-（三甲基氨基）丙基]甲基] -8-甲氧基补骨脂素的一系列衍生物合成，并研究其作为PUVA试剂的潜力。虽然发现所选补骨脂素的DNA缔合常数为10（5）-10（6）L mol-1，与有效结合相对应，但流式线性二色性研究表明，只有8个取代的补骨脂素通过嵌入与DNA结合。此外，体外在小牛胸腺DNA中光诱导链间交联的能力与8-取代的补骨脂素的8-甲氧基补骨脂素一样有效，其效率是5-取代的补骨脂素的25倍。对所研究的补骨脂素中的四个进行了放射性标记，并用于研究与DNA的光结合。与交叉绑定结果类似，8取代的补骨脂素比5取代的补骨脂素更有效地进行光键合，而光结合交联比只有很小的差异。与8-甲氧基补骨脂素相比，氨基补骨脂素对环己烯和2'-脱氧胸苷的光反应性得到增强，当氨基接近呋喃香豆素环系统时，这种作用最为明显。在体外，大多数新化合物对NHIK
• 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.