3-(acetoxymethyl)-2H-benzofuro<3,2-g>-1-benzopyran-2-one | 245736-94-1

• 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: 3-(acetoxymethyl)-2H-benzofuro<3,2-g>-1-benzopyran-2-one
• 英文别名: (2-Oxo-[1]benzofuro[3,2-g]chromen-3-yl)methyl acetate
• CAS: 245736-94-1
• 化学式: C₁₈H₁₂O₅
• 分子量: 308.29
• InChiKey: IZHLGTCJPSPLRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  65.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(acetoxymethyl)-2H-benzofuro<3,2-g>-1-benzopyran-2-one 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以59%的产率得到3-(Hydroxymethyl)-[1]benzofuro[3,2-g]chromen-2-one
  参考文献：
  名称：

  Synthesis and Biological Activity of (Hydroxymethyl)- and (Diethylaminomethyl)benzopsoralens

  摘要：

  Some benzopsoralens, carrying a hydroxymethyl or a diethylaminomethyl group at the 3, 5, 8, and 11 positions, were prepared, and their biological activity was compared with that of 4-(hydroxymethyl)benzopsoralen (BP). 5-(Hydroxymethyl)benzopsoralen (7b), 11-(hydroxymethyl)benzopsoralen (7c), and 11-(diethylaminomethyl)benzopsoralen (8c) induced marked antiproliferative effects in mammalian cells by simple incubation in the dark; this activity appeared to be related to their ability to inhibit topoisomerase II. Benzopsoralens appeared to be more active, especially BP and 7c, upon WA activation. Compounds carrying a methyl group at the 4 position together with a hydroxymethyl Or diethylaminomethyl at the 8 position (7d and 8d, respectively) were also effective, although to a lower extent; instead, a substituent at the 3 position canceled all activity. Benzopsoralens did not induce interstrand cross-links in DNA in vitro, as seen in the induction of cytoplasmic <> mutations and double-strand breaks in yeast. This behavior is also compatible with their low mutagenic activity in E. coli WP2 and with the absence of any phototoxicity on the skin. For these features, benzopsoralens seem to be interesting potential drugs for PUVA photochemotherapy and photopheresis. The activity shown in the dark is not sufficient for their possible use as antitumor drugs, but it does offer a new model for the study of topoisomerase inhibitors.

  DOI：

  10.1021/jm991028s
• 作为产物：
  描述：

  3-methyl-2H-benzofuro<3,2-g>-1-benzopyran-2-one 在 N-溴代丁二酰亚胺(NBS) 、 乙酸酐 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 3-(acetoxymethyl)-2H-benzofuro<3,2-g>-1-benzopyran-2-one
  参考文献：
  名称：

  Synthesis and Biological Activity of (Hydroxymethyl)- and (Diethylaminomethyl)benzopsoralens

  摘要：

  Some benzopsoralens, carrying a hydroxymethyl or a diethylaminomethyl group at the 3, 5, 8, and 11 positions, were prepared, and their biological activity was compared with that of 4-(hydroxymethyl)benzopsoralen (BP). 5-(Hydroxymethyl)benzopsoralen (7b), 11-(hydroxymethyl)benzopsoralen (7c), and 11-(diethylaminomethyl)benzopsoralen (8c) induced marked antiproliferative effects in mammalian cells by simple incubation in the dark; this activity appeared to be related to their ability to inhibit topoisomerase II. Benzopsoralens appeared to be more active, especially BP and 7c, upon WA activation. Compounds carrying a methyl group at the 4 position together with a hydroxymethyl Or diethylaminomethyl at the 8 position (7d and 8d, respectively) were also effective, although to a lower extent; instead, a substituent at the 3 position canceled all activity. Benzopsoralens did not induce interstrand cross-links in DNA in vitro, as seen in the induction of cytoplasmic <> mutations and double-strand breaks in yeast. This behavior is also compatible with their low mutagenic activity in E. coli WP2 and with the absence of any phototoxicity on the skin. For these features, benzopsoralens seem to be interesting potential drugs for PUVA photochemotherapy and photopheresis. The activity shown in the dark is not sufficient for their possible use as antitumor drugs, but it does offer a new model for the study of topoisomerase inhibitors.

  DOI：

  10.1021/jm991028s

文献信息

• Synthesis and Biological Activity of (Hydroxymethyl)- and (Diethylaminomethyl)benzopsoralens
  作者：Adriana Chilin、Cristina Marzano、Adriano Guiotto,*、Paolo Manzini、Francarosa Baccichetti、Francesco Carlassare、Franco Bordin

  DOI：10.1021/jm991028s

  日期：1999.7.1

  Some benzopsoralens, carrying a hydroxymethyl or a diethylaminomethyl group at the 3, 5, 8, and 11 positions, were prepared, and their biological activity was compared with that of 4-(hydroxymethyl)benzopsoralen (BP). 5-(Hydroxymethyl)benzopsoralen (7b), 11-(hydroxymethyl)benzopsoralen (7c), and 11-(diethylaminomethyl)benzopsoralen (8c) induced marked antiproliferative effects in mammalian cells by simple incubation in the dark; this activity appeared to be related to their ability to inhibit topoisomerase II. Benzopsoralens appeared to be more active, especially BP and 7c, upon WA activation. Compounds carrying a methyl group at the 4 position together with a hydroxymethyl Or diethylaminomethyl at the 8 position (7d and 8d, respectively) were also effective, although to a lower extent; instead, a substituent at the 3 position canceled all activity. Benzopsoralens did not induce interstrand cross-links in DNA in vitro, as seen in the induction of cytoplasmic <> mutations and double-strand breaks in yeast. This behavior is also compatible with their low mutagenic activity in E. coli WP2 and with the absence of any phototoxicity on the skin. For these features, benzopsoralens seem to be interesting potential drugs for PUVA photochemotherapy and photopheresis. The activity shown in the dark is not sufficient for their possible use as antitumor drugs, but it does offer a new model for the study of topoisomerase inhibitors.