5-Methoxy-4-methyl-8,9,10,11-tetrahydro-[1]benzofuro[2,3-h]chromen-2-one | 161837-63-4

• 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: 5-Methoxy-4-methyl-8,9,10,11-tetrahydro-[1]benzofuro[2,3-h]chromen-2-one
• CAS: 161837-63-4
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: RVEHOXTWIWYQJQ-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：

  5-Methoxy-4-methyl-8,9,10,11-tetrahydro-[1]benzofuro[2,3-h]chromen-2-one 在 六甲基磷酰三胺 、 氢碘酸 、 乙酸酐 、 potassium carbonate 、 溶剂黄146 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 丙酮 、 苯 为溶剂， 反应 4.0h， 生成 5-(3-dimethylaminopropoxy)-4-methylbenzofuro[2,3-h]coumarin
  参考文献：
  名称：

  A new benzoangelicin with strong photobiological activity

  摘要：

  Benzoangelicins 4-6 were synthesized in good yields from 7-hydroxy-5-methoxy-4-methylcoumarin (1). In the absence of UVA radiation, compounds 5 and 6 were only weakly active against HL60 and HeLa tumour cells; in its presence, compound 6 was 10 times more active than the reference compound 8-methoxypsoralen. None of 4-6 exhibited cutaneous phototoxicity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00640-x
• 作为产物：
  描述：

  夫拉美诺 在 sodium hydroxide 、 硫酸 、 水 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 18.0h， 生成 5-Methoxy-4-methyl-8,9,10,11-tetrahydro-[1]benzofuro[2,3-h]chromen-2-one
  参考文献：
  名称：

  Antonello, Cipriano; Zagotto, Giuseppe; Miranda, Rocio, Bulletin des Societes Chimiques Belges, 1994, vol. 103, # 11, p. 651 - 654

  摘要：

  DOI：

文献信息

• 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。
• A novel tetrahydrobenzoangelicin with dark and photo biological activity
  作者：Lisa Dalla Via、Ornella Gia、Sergio Caffieri、Aída N. García-Argáez、Elías Quezada、Eugenio Uriarte

  DOI：10.1016/j.bmc.2012.03.071

  日期：2012.6

  The synthesis of 8,9,10,11-tetrahydro-5-(3-dimethylaminopropoxy)-4-methylbenzofuro[2,3-h] coumarin (5) is described. The new compound showed the ability to inhibit cell growth both upon UVA irradiation and in the dark. The investigation on the mechanism of action highlighted the capacity of 5 to covalently photoadd to thymine, as demonstrated by the isolation and characterization of the 4',5'-monoadduct. Furthermore, in the ground state 5 interferes with the topoisomerase II relaxation activity, suggesting that this enzyme could constitute a molecular target responsible for the dark antiproliferative effect. (C) 2012 Elsevier Ltd. All rights reserved.
• Antonello, Cipriano; Zagotto, Giuseppe; Miranda, Rocio, Bulletin des Societes Chimiques Belges, 1994, vol. 103, # 11, p. 651 - 654
  作者：Antonello, Cipriano、Zagotto, Giuseppe、Miranda, Rocio、Uriarte, Eugenio

  DOI：——

  日期：——
• A new benzoangelicin with strong photobiological activity
  作者：Lourdes Santana、Eugenio Uriarte、Lisa Dalla Via、Ornella Gia

  DOI：10.1016/s0960-894x(99)00640-x

  日期：2000.1

  Benzoangelicins 4-6 were synthesized in good yields from 7-hydroxy-5-methoxy-4-methylcoumarin (1). In the absence of UVA radiation, compounds 5 and 6 were only weakly active against HL60 and HeLa tumour cells; in its presence, compound 6 was 10 times more active than the reference compound 8-methoxypsoralen. None of 4-6 exhibited cutaneous phototoxicity. (C) 2000 Elsevier Science Ltd. All rights reserved.