6-Hydroxy-1-methyl-[1]benzofuro[2,3-f]chromen-3-one | 195320-34-4

• 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: 6-Hydroxy-1-methyl-[1]benzofuro[2,3-f]chromen-3-one
• CAS: 195320-34-4
• 化学式: C₁₆H₁₀O₄
• 分子量: 266.253
• InChiKey: JSYOHFFQONDFEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  6-Hydroxy-1-methyl-[1]benzofuro[2,3-f]chromen-3-one 、 N,N-二甲氨基氯丙烷盐酸盐 在 sodium hydride 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以64%的产率得到6-[3-(Dimethylamino)propoxy]-1-methyl-3H-benzofuro[2,3-f][1]benzopyran-3-one
  参考文献：
  名称：

  New Furan Side Tetracyclic Allopsoralen Derivatives:  Synthesis and Photobiological Evaluation

  摘要：

  Novel tetracyclic allopsoralen derivatives characterized by the condensation of a fourth cyclohexenylic ( 57) or benzenic (8-10) ring at the furan side and a methoxy ( 5 and 8), a hydroxy ( 6 and 9), or a dimethylaminopropoxy ( 7 and 10) side chain in the 10 position of the chromophore were prepared. Compounds 7 and 10 showed a strong photoantiproliferative activity, up to 3 orders of magnitude higher than that of the photochemotherapeutic drug 8-methoxypsoralen (8-MOP). The investigation into the mechanism of action demonstrated for 10 the capacity to intercalate between DNA base pairs in the ground state, to give rise to a covalent photoaddition upon UVA irradiation, and to inhibit polymerase chain reaction (PCR) in a sequence-specific manner. Conversely, compound 7 showed a limited capacity to form an intercalative complex and the lack of ability to photoadd to the macromolecule, thus revealing a novel and unusual behavior for an allopsoralen derivative.

  DOI：

  10.1021/jm058032q
• 作为产物：
  描述：

  6-Methoxy-1-methyl-4,11-dioxa-benzo[a]fluoren-3-one 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以94%的产率得到6-Hydroxy-1-methyl-[1]benzofuro[2,3-f]chromen-3-one
  参考文献：
  名称：

  New Furan Side Tetracyclic Allopsoralen Derivatives:  Synthesis and Photobiological Evaluation

  摘要：

  Novel tetracyclic allopsoralen derivatives characterized by the condensation of a fourth cyclohexenylic ( 57) or benzenic (8-10) ring at the furan side and a methoxy ( 5 and 8), a hydroxy ( 6 and 9), or a dimethylaminopropoxy ( 7 and 10) side chain in the 10 position of the chromophore were prepared. Compounds 7 and 10 showed a strong photoantiproliferative activity, up to 3 orders of magnitude higher than that of the photochemotherapeutic drug 8-methoxypsoralen (8-MOP). The investigation into the mechanism of action demonstrated for 10 the capacity to intercalate between DNA base pairs in the ground state, to give rise to a covalent photoaddition upon UVA irradiation, and to inhibit polymerase chain reaction (PCR) in a sequence-specific manner. Conversely, compound 7 showed a limited capacity to form an intercalative complex and the lack of ability to photoadd to the macromolecule, thus revealing a novel and unusual behavior for an allopsoralen derivative.

  DOI：

  10.1021/jm058032q

文献信息

• New Furan Side Tetracyclic Allopsoralen Derivatives:  Synthesis and Photobiological Evaluation
  作者：Lisa Dalla Via、Stefano Mammi、Eugenio Uriarte、Lourdes Santana、Ilaria Lampronti、Roberto Gambari、Ornella Gia

  DOI：10.1021/jm058032q

  日期：2006.7.1

  Novel tetracyclic allopsoralen derivatives characterized by the condensation of a fourth cyclohexenylic ( 57) or benzenic (8-10) ring at the furan side and a methoxy ( 5 and 8), a hydroxy ( 6 and 9), or a dimethylaminopropoxy ( 7 and 10) side chain in the 10 position of the chromophore were prepared. Compounds 7 and 10 showed a strong photoantiproliferative activity, up to 3 orders of magnitude higher than that of the photochemotherapeutic drug 8-methoxypsoralen (8-MOP). The investigation into the mechanism of action demonstrated for 10 the capacity to intercalate between DNA base pairs in the ground state, to give rise to a covalent photoaddition upon UVA irradiation, and to inhibit polymerase chain reaction (PCR) in a sequence-specific manner. Conversely, compound 7 showed a limited capacity to form an intercalative complex and the lack of ability to photoadd to the macromolecule, thus revealing a novel and unusual behavior for an allopsoralen derivative.