3-[2-bis(1-methylethylamino)ethoxy]benzo[b]naphtho[2,3-d]furan-6,11-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 3-[2-bis(1-methylethylamino)ethoxy]benzo[b]naphtho[2,3-d]furan-6,11-dione
• 英文别名: 3-[2-[Di(propan-2-yl)amino]ethoxy]naphtho[3,2-b][1]benzofuran-6,11-dione
• 化学式: C₂₄H₂₅NO₄
• 分子量: 391.467
• InChiKey: OBPYWCNNZZRYSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  59.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  间苯二酚 在 苄基三乙基氯化铵 、 potassium carbonate 作用下， 以 氯仿 、 水 为溶剂， 生成 3-[2-bis(1-methylethylamino)ethoxy]benzo[b]naphtho[2,3-d]furan-6,11-dione
  参考文献：
  名称：

  Synthesis, cytotoxicity, and DNA topoisomerase II inhibitory activity of benzofuroquinolinediones

  摘要：

  Benzofuroquinolinediones (7c and 7d) were synthesized by base-catalyzed condensation of dichloroquinolinediones with phenolic derivatives. Their dialkylaminoalkoxy derivatives (8i-8p) were prepared by reaction with various dialkylaminoalkyl chlorides. The cytotoxicity of the synthesized compounds was evaluated against eight types of human cancer cell lines, and their topoisomerase II inhibition was assessed. In general, the cytotoxicity of benzofuroquinolinediones (8i-8p) was similar or superior to that of doxorubicin and showed more potent inhibitory activity than naphthofurandiones (8a-8h). Also, most of the compounds exhibited excellent topoisomerase II inhibitory activity at a concentration of 5 mu M and two compounds, 8d and 8i, showed IC50 values of inhibitory activity at a concentration of 5 mu M and two compounds, 8d and 8i, showed IC50 values of 1.19 and 0.68 mu M, respectively, and were much more potent than etoposide (IC50 = 78.4 mu M), but similar to doxorubicin (IC50 = 2.67 mu M). However their inhibitory activity on topoisomerase I was lower, and 8d and 8i showed IC50 values of 42.0 and 64.3 mu M, respectively. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.12.012

文献信息

• Synthesis, cytotoxicity, and DNA topoisomerase II inhibitory activity of benzofuroquinolinediones
  作者：Hee-Kyung Rhee、Hyen Joo Park、Sang Kook Lee、Chong-Ock Lee、Hea-Young Park Choo

  DOI：10.1016/j.bmc.2006.12.012

  日期：2007.2

  Benzofuroquinolinediones (7c and 7d) were synthesized by base-catalyzed condensation of dichloroquinolinediones with phenolic derivatives. Their dialkylaminoalkoxy derivatives (8i-8p) were prepared by reaction with various dialkylaminoalkyl chlorides. The cytotoxicity of the synthesized compounds was evaluated against eight types of human cancer cell lines, and their topoisomerase II inhibition was assessed. In general, the cytotoxicity of benzofuroquinolinediones (8i-8p) was similar or superior to that of doxorubicin and showed more potent inhibitory activity than naphthofurandiones (8a-8h). Also, most of the compounds exhibited excellent topoisomerase II inhibitory activity at a concentration of 5 mu M and two compounds, 8d and 8i, showed IC50 values of inhibitory activity at a concentration of 5 mu M and two compounds, 8d and 8i, showed IC50 values of 1.19 and 0.68 mu M, respectively, and were much more potent than etoposide (IC50 = 78.4 mu M), but similar to doxorubicin (IC50 = 2.67 mu M). However their inhibitory activity on topoisomerase I was lower, and 8d and 8i showed IC50 values of 42.0 and 64.3 mu M, respectively. (c) 2007 Elsevier Ltd. All rights reserved.