4,6-dimethylpyranocoumarin | 107265-13-4

• 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: 4,6-dimethylpyranocoumarin
• 英文别名: 4,6-dimethyl-2H,8H-benzo<1,2-b;3,4-b'>dipyran-2-one；4,6-dimethyl-8H-pyrano[6,5-f]chromen-2-one；4,6-dimethyl-8H-pyrano[2,3-h]chromen-2-one
• CAS: 107265-13-4
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: ZKFDLWNLBBSHRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,6-dimethylpyranocoumarin 、 alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 作用下， 生成
  参考文献：
  名称：

  Pyranocoumarins as potential photochemotherapeutic agents: theoretical and physico-chemical studies on the mechanism of action

  摘要：

  The interactions between 2 angular pyranocoumarins and DNA have been studied in both ground and excited states. The compounds are able to intercalate inside DNA in a non-covalent manner and, under UV-A irradiation, to photobind covalently, forming pyran-side monoadducts and cross-links. The crystal structure of 4,6-dimethylpyranocoumarin was determined by X-ray diffraction techniques, and molecular arrangements in both ground and excited (singlet and triplet) states were calculated by the MNDO method. Results are discussed in terms of intercalation in the ground state, as shown by linear dichroism measurements, and covalent photobinding to pyrimidine bases of DNA under UV-A excitation.

  DOI：

  10.1016/0223-5234(91)90130-f
• 作为产物：
  描述：

  4,6-dimethyl-7-propargyloxycoumarin 以 various solvent(s) 为溶剂， 以51%的产率得到4,6-dimethylpyranocoumarin
  参考文献：
  名称：

  合成8-去甲基黄嘌呤和8-去甲基正己烷的甲基衍生物，潜在的抗增殖剂

  摘要：

  合成了许多与8-去甲基黄嘌呤和8-去甲基正己烷有关的吡喃香豆素的新甲基衍生物。通过在沸腾的N，N-二乙基苯胺的7-羟基香豆素的合适的甲基衍生物的炔丙基或甲基炔丙基醚中环化进行合成。甲基已被引入到看起来最有希望增强化合物对DNA的光反应性的位置。

  DOI：

  10.1002/jhet.5570240234

文献信息

• RODIGHIERO P.; MANZINI P.; PASTORINI G.; BORDIN F.; GUIOTTO A., J. HETEROCYCL. CHEM., 24,(1987) N 2, 485-488
  作者：RODIGHIERO P.、 MANZINI P.、 PASTORINI G.、 BORDIN F.、 GUIOTTO A.

  DOI：——

  日期：——
• Synthesis of methyl derivatives of 8-desmethylxanthyletine and 8-desmethylseseline, potential antiproliferative agents
  作者：P. Rodighiero、P. Manzini、G. Pastorini、F. Bordin、A. Guiotto

  DOI：10.1002/jhet.5570240234

  日期：1987.3

  A number of new methyl derivatives of pyranocoumarins, related to 8-desmethylxanthyletine and to 8-desmethylseseline, were synthesized. The syntheses were performed by cyclization in boiling N,N-diethyl aniline of the propargyl or methylpropargyl ethers of the appropriate methyl derivatives of 7-hydroxycou-marin. Methyl groups have been introduced into positions which look most promising for enhancement

  合成了许多与8-去甲基黄嘌呤和8-去甲基正己烷有关的吡喃香豆素的新甲基衍生物。通过在沸腾的N，N-二乙基苯胺的7-羟基香豆素的合适的甲基衍生物的炔丙基或甲基炔丙基醚中环化进行合成。甲基已被引入到看起来最有希望增强化合物对DNA的光反应性的位置。
• Pyranocoumarins as potential photochemotherapeutic agents: theoretical and physico-chemical studies on the mechanism of action
  作者：D Vedaldi、P Rodighiero、F Orsini、V Lucchini、F Dall'Acqua、S Caffieri、G Bombieri、F Benetollo

  DOI：10.1016/0223-5234(91)90130-f

  日期：1991.12

  The interactions between 2 angular pyranocoumarins and DNA have been studied in both ground and excited states. The compounds are able to intercalate inside DNA in a non-covalent manner and, under UV-A irradiation, to photobind covalently, forming pyran-side monoadducts and cross-links. The crystal structure of 4,6-dimethylpyranocoumarin was determined by X-ray diffraction techniques, and molecular arrangements in both ground and excited (singlet and triplet) states were calculated by the MNDO method. Results are discussed in terms of intercalation in the ground state, as shown by linear dichroism measurements, and covalent photobinding to pyrimidine bases of DNA under UV-A excitation.