3-(2-Diethylamino-ethoxy)-1-hydroxy-anthraquinone

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 3-(2-Diethylamino-ethoxy)-1-hydroxy-anthraquinone
• 英文别名: 3-[2-(Diethylamino)ethoxy]-1-hydroxyanthracene-9,10-dione
• 化学式: C₂₀H₂₁NO₄
• 分子量: 339.391
• InChiKey: GQBYBBMWWSAPPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,3-二羥蒽醌 在 氢氧化钾 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 38.0h， 生成 3-(2-Diethylamino-ethoxy)-1-hydroxy-anthraquinone
  参考文献：
  名称：

  Synthesis and cytotoxic effect of 1,3-dihydroxy-9,10-anthraquinone derivatives

  摘要：

  1,3-Dihydroxy-9,10-anthraquinone (4) was reacted with epichlorohydrin or 1,omega -dibromo-alkane to yield 1-hydroxy-3-(2,3-epoxypropoxy)-9, 10-anthraquinone (5) and 1-hydroxy-3-(3-chloro-2-hydroxypropoxy) (6) or 1-hydroxy-3-(omega -bromoalkoxy)-9,10-anthraquinone. Ring-opening of the epoxide (5) or 1-hydroxy-3-(omega -bromoalkoxy)-9,10-anthraquinones with appropriate amines, afforded various 1-hydroxy-3-(3-alkylamino-2-hydroxypropoxy)-9,10-anthraquinones. The synthetic compounds were tested in vitro inhibition of human T-24, Hep 3B, Hep G2, SiHa, HT-3, PLC/PRF/5 and 212 cells. Almost all compounds showed significant inhibitory activity against several different cancer cell lines. Structure-activity analysis indicated epoxidation of the hydroxyanthraquinone increased cytotoxicity against tumour cells, but ring-opening of the epoxide group with amine did not enhance the cytotoxic activity. The phosphatidylserine (PS) externalization and DNA fragmentation in SiHa cells were significantly observed after 48 h incubation with selected compound 19. The results show that 19 cause cell death by apoptosis. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)01190-9

文献信息

• Synthesis and cytotoxic effect of 1,3-dihydroxy-9,10-anthraquinone derivatives
  作者：Bai-Luh Wei、Szu-Huei Wu、Mei-Ing Chung、Shen-Jeu Won、Chun-Nan Lin

  DOI：10.1016/s0223-5234(00)01190-9

  日期：2000.12

  1,3-Dihydroxy-9,10-anthraquinone (4) was reacted with epichlorohydrin or 1,omega -dibromo-alkane to yield 1-hydroxy-3-(2,3-epoxypropoxy)-9, 10-anthraquinone (5) and 1-hydroxy-3-(3-chloro-2-hydroxypropoxy) (6) or 1-hydroxy-3-(omega -bromoalkoxy)-9,10-anthraquinone. Ring-opening of the epoxide (5) or 1-hydroxy-3-(omega -bromoalkoxy)-9,10-anthraquinones with appropriate amines, afforded various 1-hydroxy-3-(3-alkylamino-2-hydroxypropoxy)-9,10-anthraquinones. The synthetic compounds were tested in vitro inhibition of human T-24, Hep 3B, Hep G2, SiHa, HT-3, PLC/PRF/5 and 212 cells. Almost all compounds showed significant inhibitory activity against several different cancer cell lines. Structure-activity analysis indicated epoxidation of the hydroxyanthraquinone increased cytotoxicity against tumour cells, but ring-opening of the epoxide group with amine did not enhance the cytotoxic activity. The phosphatidylserine (PS) externalization and DNA fragmentation in SiHa cells were significantly observed after 48 h incubation with selected compound 19. The results show that 19 cause cell death by apoptosis. (C) 2000 Editions scientifiques et medicales Elsevier SAS.