6-Methoxy-1-methyl-7,8,9,10-tetrahydro-4,11-dioxa-benzo[a]fluoren-3-one | 195320-30-0

• 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: 6-Methoxy-1-methyl-7,8,9,10-tetrahydro-4,11-dioxa-benzo[a]fluoren-3-one
• 英文别名: 6-Methoxy-1-methyl-7,8,9,10-tetrahydro-[1]benzofuro[2,3-f]chromen-3-one
• CAS: 195320-30-0
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: UHMJHRFXKDJWQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  6-Methoxy-1-methyl-7,8,9,10-tetrahydro-4,11-dioxa-benzo[a]fluoren-3-one 在 三氯化铝 、 sodium hydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 sodium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 13.0h， 生成 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：

  7-methoxy-4-methyl-5-(2-oxocyclohexyloxy)-2H-chromen-2-one 在 sodium hydroxide 作用下， 反应 3.0h， 以69%的产率得到6-Methoxy-1-methyl-7,8,9,10-tetrahydro-4,11-dioxa-benzo[a]fluoren-3-one
  参考文献：
  名称：

  Synthesis of Linear and Angular Benzofurocoumarins

  摘要：

  描述了取代的线性和有角苯并呋喃香豆素的四步合成方法。从 5-甲氧基间苯二酚开始，这种方法获得了苯并补骨脂素 (7)、苯并当归素 (8) 和苯并别补骨脂素 (11) 的良好产率，它们带有容易水解的甲氧基，因此可以得到其他有潜力作为光化疗剂的取代化合物。

  DOI：

  10.1055/s-1997-1381

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.
• Synthesis of Linear and Angular Benzofurocoumarins
  作者：Carmen Terán、Rocio Miranda、Lourdes Santana、Marta Teijeira、Eugenio Uriarte

  DOI：10.1055/s-1997-1381

  日期：1997.12

  A four-step synthetic approach to substituted linear and angular benzofurocoumarins is described. Starting from 5-methoxyresorcinol, this approach afforded good yields of benzopsoralen (7), benzoangelicine (8), and benzoallopsoralen (11), which bear easily hydrolysed methoxy groups and thus allow access to other substituted compounds with potential as photochemotherapeutic agents.

  描述了取代的线性和有角苯并呋喃香豆素的四步合成方法。从 5-甲氧基间苯二酚开始，这种方法获得了苯并补骨脂素 (7)、苯并当归素 (8) 和苯并别补骨脂素 (11) 的良好产率，它们带有容易水解的甲氧基，因此可以得到其他有潜力作为光化疗剂的取代化合物。