4-methyl-8-methoxypsoralen | 5263-08-1

• 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-methoxypsoralen
• 英文别名: 9-methoxy-5-methyl-furo[3,2-g]chromen-7-one；9-Methoxy-5-methyl-furo[3,2-g]chromen-7-on；9-methoxy-5-methyl-7H-furo[3,2-g][1]benzopyran-7-one；7H-Furo(3,2-g)(1)benzopyran-7-one, 9-methoxy-5-methyl-；9-methoxy-5-methylfuro[3,2-g]chromen-7-one
• CAS: 5263-08-1
• 化学式: C₁₃H₁₀O₄
• 分子量: 230.22
• InChiKey: GHHPLROQBQKAFI-UHFFFAOYSA-N

物化性质

• 熔点：
  167-168 °C
• 沸点：
  415.6±45.0 °C(Predicted)
• 密度：
  1.308±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  1
• 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：

  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
• 作为产物：
  描述：

  9-methoxy-5-methyl-7-oxo-7H-furo[3,2-g]chromene-2-carboxylic acid 在 calcium carbonate 作用下， 生成 4-methyl-8-methoxypsoralen
  参考文献：
  名称：

  Antonello, Gazzetta Chimica Italiana, 1958, vol. 88, p. 430,433

  摘要：

  DOI：

文献信息

• 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％）。
• 8-Methoxypsoralen derivatives
  申请人：Hoffmann-La Roche Inc.

  公开号：US04130568A1

  公开（公告）日：1978-12-19

  The invention relates to synthetic processes to produce the known pharmacologically active 8-methoxypsoralen and derivatives thereof. Also disclosed are various novel intermediates utilized in these processes.

  本发明涉及用于生产已知药理活性的8-甲氧基紫檀酚及其衍生物的合成过程。还公开了在这些过程中使用的各种新型中间体。
• US4130568A
  申请人：——

  公开号：US4130568A

  公开（公告）日：1978-12-19
• US4180659A
  申请人：——

  公开号：US4180659A

  公开（公告）日：1979-12-25
• Antonello, Gazzetta Chimica Italiana, 1958, vol. 88, p. 430,433
  作者：Antonello

  DOI：——

  日期：——