4-methyl-8-hydroxypsoralen | 88589-76-8

• 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: 4-methyl-8-hydroxypsoralen
• 英文别名: 4-methyl-8-hydroxylpsoralen；9-Hydroxy-5-methyl-7H-furo[3,2-g][1]benzopyran-7-one；9-hydroxy-5-methylfuro[3,2-g]chromen-7-one
• CAS: 88589-76-8
• 化学式: C₁₂H₈O₄
• 分子量: 216.193
• InChiKey: GMUKRCCECVRGDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methyl-8-hydroxypsoralen 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 21.0h， 生成 4-methyl-8-<3H3>methoxypsoralen
  参考文献：
  名称：

  8-甲氧基补骨脂素-核酸光反应。甲基取代对吡喃酮与呋喃光加成反应的影响。

  摘要：

  我们合成了一系列的8- [3H]甲氧基补骨脂素，其中的甲基和氢在4-和5'-位上系统地变化。对这四种补骨脂素与核酸聚（dA-dT）的光加成反应产生的产物的分析表明，产物的分布取决于4-甲基取代基的存在与否。具有4-甲基的化合物显示出对呋喃双键加成的压倒性优势（约98％），而没有4-甲基的化合物显示出对吡喃酮双键的加成量大（约18％）。

  DOI：

  10.1021/jm00370a017
• 作为产物：
  描述：

  4-methyl-8-methoxypsoralen 在 三溴化硼 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以93%的产率得到4-methyl-8-hydroxypsoralen
  参考文献：
  名称：

  Synthesis of methyl-substituted xanthotoxol to clarify prooxidant effect of methyl on radical-induced oxidation of DNA

  摘要：

  4-Methyl-8-hydroxylpsoralen (MXan) and 4,9-dimethy1-8-hydroxylpsoralen (DMXan) were synthesized in order to clarify the effect of methyl on the antioxidant effectiveness of xanthotoxol (8-hydroxyl-psoralen, Xan), which were assessed by bleaching beta-carotene in linoleic acid-Triton emulsion, by interacting with 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS(+))center dot, 2,2'-dipheny1-1-picrylhydrazyl radical (DPPH), and galvinoxyl radical, and by protecting DNA against the oxidation induced by Cu(2+)/glutathione (GSH) and 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH). Methyl attaching to xanthotoxol did not affect its ability to protect linoleic acid against autoxidation and to inhibit Cu(2+)/GSH-induced oxidation DNA, but decreased its ability to scavenge ABTS(+)center dot and DPPH, and to protect DNA against AAPH-induced oxidation. Therefore, methyl attenuated the antioxidant effectiveness of xanthotoxol in radical-induced oxidation of DNA.

  DOI：

  10.1016/j.ejmech.2010.02.044

文献信息

• Synthesis of methyl-substituted xanthotoxol to clarify prooxidant effect of methyl on radical-induced oxidation of DNA
  作者：Chuan Xiao、Zhi-Guang Song、Zai-Qun Liu

  DOI：10.1016/j.ejmech.2010.02.044

  日期：2010.6

  4-Methyl-8-hydroxylpsoralen (MXan) and 4,9-dimethy1-8-hydroxylpsoralen (DMXan) were synthesized in order to clarify the effect of methyl on the antioxidant effectiveness of xanthotoxol (8-hydroxyl-psoralen, Xan), which were assessed by bleaching beta-carotene in linoleic acid-Triton emulsion, by interacting with 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS(+))center dot, 2,2'-dipheny1-1-picrylhydrazyl radical (DPPH), and galvinoxyl radical, and by protecting DNA against the oxidation induced by Cu(2+)/glutathione (GSH) and 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH). Methyl attaching to xanthotoxol did not affect its ability to protect linoleic acid against autoxidation and to inhibit Cu(2+)/GSH-induced oxidation DNA, but decreased its ability to scavenge ABTS(+)center dot and DPPH, and to protect DNA against AAPH-induced oxidation. Therefore, methyl attenuated the antioxidant effectiveness of xanthotoxol in radical-induced oxidation of DNA.
• 8-Methoxypsoralen-nucleic acid photoreaction. Effect of methyl substitution on pyrone vs. furan photoaddition
  作者：David Kanne、Henry Rapoport、John E. Hearst

  DOI：10.1021/jm00370a017

  日期：1984.4

  We have synthesized a series of 8-[3H]methoxypsoralens in which methyl and hydrogen are systematically varied at the 4- and 5'-positions. Analysis of the products resulting from the photoaddition of these four psoralens with the nucleic acid poly(dA-dT) reveals that the product distribution depends on the presence or absence of a 4-methyl substituent. Compounds with the 4-methyl group show an overwhelming

  我们合成了一系列的8- [3H]甲氧基补骨脂素，其中的甲基和氢在4-和5'-位上系统地变化。对这四种补骨脂素与核酸聚（dA-dT）的光加成反应产生的产物的分析表明，产物的分布取决于4-甲基取代基的存在与否。具有4-甲基的化合物显示出对呋喃双键加成的压倒性优势（约98％），而没有4-甲基的化合物显示出对吡喃酮双键的加成量大（约18％）。