6,7,8,9-tetrahydro-11-methoxy-4-methyl-2H-benzofuro<3,2-g>-1-benzopyran-2-one | 167023-41-8

• 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: 6,7,8,9-tetrahydro-11-methoxy-4-methyl-2H-benzofuro<3,2-g>-1-benzopyran-2-one
• 英文别名: 11-Methoxy-4-methyl-6,7,8,9-tetrahydro-[1]benzofuro[3,2-g]chromen-2-one
• CAS: 167023-41-8
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: FBYMFNPUZLFFME-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：

  6,7,8,9-tetrahydro-11-methoxy-4-methyl-2H-benzofuro<3,2-g>-1-benzopyran-2-one 在 三氯化铝 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 8.0h， 生成 11-hydroxy-4-methyl-2H-benzofuro<3,2-g>-1-benzopyran-2-one
  参考文献：
  名称：

  New Tetracyclic Analogues of Photochemotherapeutic Drugs 5-MOP and 8-MOP:  Synthesis, DNA Interaction, and Antiproliferative Activity

  摘要：

  The synthesis of new tetrahydrobenzo- and benzopsoralen derivatives carrying at position 5 or 8 of the furocoumarin moiety a methoxy, hydroxy, or dimethylaminopropoxy side chain is reported. The study of their photoantiproliferative activity and ability to induce erythema on guinea pig skin allows us to state that the derivatives carrying the dimethylaminopropoxy side. chain exhibit a very interesting photobiological pattern. Indeed, if compared with the lead compounds 5-MOP and 8-MOP, they exert a higher cytotoxic activity devoid of significant skin phototoxicity. Between them, the more interesting appears to be 16, a nonphototoxic compound whose antiproliferative activity on HeLa cells is 2 orders of magnitude higher than that of the reference drug 8-MOP. Photoreaction experiments have revealed that, like classic furocoumarins, A-T is the preferred nucleic base pair in its photobinding. Moreover, the extent of covalent photoaddition to DNA correlates well with the photobiological activity. For this compound a certain effect was also observed in the dark. Evaluation of the ability to induce DNA cleavage in the presence of human topoisomerase II has suggested that this enzyme is probably the target accountable for this effect.

  DOI：

  10.1021/jm9910829
• 作为产物：
  描述：

  2-氯环己酮 在 三乙胺 、 sodium hydroxide 作用下， 以 水 、 异丙醇 为溶剂， 反应 0.41h， 生成 6,7,8,9-tetrahydro-11-methoxy-4-methyl-2H-benzofuro<3,2-g>-1-benzopyran-2-one
  参考文献：
  名称：

  补骨脂醌作为一类新型的蛋白酶体抑制剂：设计，合成和生物学评价。

  摘要：

  蛋白酶体亚基特异性：补骨脂醌被鉴定为一类新的非肽蛋白酶体抑制剂。取决于脚手架装饰，这些化合物表现出令人感兴趣的亚基特异性。与Thr1，Thr21和Ser129的相互作用对于抑制至关重要。

  DOI：

  10.1002/cmdc.201100041

文献信息

• Synthesis of Benzopsoralenquinone Derivatives
  作者：A. Chilin、G. Pastorini、A. Castellin、F. Bordin、P. Rodighiero、A. Guiotto

  DOI：10.1055/s-1995-4051

  日期：1995.9

  Benzopsoralenquinone derivatives have been synthesized by linear annulation of a benzofuran moiety to the coumarin system and by selective oxidation to obtain the p-quinone function.

  通过将苯并呋喃分子与香豆素体系进行线性环化，并通过选择性氧化作用获得对醌功能，合成了苯并吡喃醌衍生物。
• New Tetracyclic Analogues of Photochemotherapeutic Drugs 5-MOP and 8-MOP:  Synthesis, DNA Interaction, and Antiproliferative Activity
  作者：Lisa Dalla Via、Ornella Gia、Sebastiano Marciani Magno、Lourdes Santana、Marta Teijeira、Eugenio Uriarte

  DOI：10.1021/jm9910829

  日期：1999.10.1

  The synthesis of new tetrahydrobenzo- and benzopsoralen derivatives carrying at position 5 or 8 of the furocoumarin moiety a methoxy, hydroxy, or dimethylaminopropoxy side chain is reported. The study of their photoantiproliferative activity and ability to induce erythema on guinea pig skin allows us to state that the derivatives carrying the dimethylaminopropoxy side. chain exhibit a very interesting photobiological pattern. Indeed, if compared with the lead compounds 5-MOP and 8-MOP, they exert a higher cytotoxic activity devoid of significant skin phototoxicity. Between them, the more interesting appears to be 16, a nonphototoxic compound whose antiproliferative activity on HeLa cells is 2 orders of magnitude higher than that of the reference drug 8-MOP. Photoreaction experiments have revealed that, like classic furocoumarins, A-T is the preferred nucleic base pair in its photobinding. Moreover, the extent of covalent photoaddition to DNA correlates well with the photobiological activity. For this compound a certain effect was also observed in the dark. Evaluation of the ability to induce DNA cleavage in the presence of human topoisomerase II has suggested that this enzyme is probably the target accountable for this effect.
• Psoralenquinones as a Novel Class of Proteasome Inhibitors: Design, Synthesis and Biological Evaluation
  作者：Giovanni Marzaro、Valentina Gandin、Christine Marzano、Adriano Guiotto、Adriana Chilin

  DOI：10.1002/cmdc.201100041

  日期：2011.6.6

  Proteasome subunit specificity: Psoralenquinones were identified as a novel class of nonpeptide proteasome inhibitors. Depending on the scaffold decoration, these compounds demonstrate interesting subunit specificity. Interactions with Thr1, Thr21 and Ser129 are critical for inhibition.

  蛋白酶体亚基特异性：补骨脂醌被鉴定为一类新的非肽蛋白酶体抑制剂。取决于脚手架装饰，这些化合物表现出令人感兴趣的亚基特异性。与Thr1，Thr21和Ser129的相互作用对于抑制至关重要。

表征谱图