3-hydroxymethyl-1,8-diazaanthraquinone | 219535-37-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-hydroxymethyl-1,8-diazaanthraquinone
• 英文别名: 3-(Hydroxymethyl)pyrido[3,2-g]quinoline-5,10-dione
• CAS: 219535-37-2
• 化学式: C₁₃H₈N₂O₃
• 分子量: 240.218
• InChiKey: ZKEHMUGJKIDIOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  80.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  氯乙基异氰酸酯 、 3-hydroxymethyl-1,8-diazaanthraquinone 在 dibutyltin diacetate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 以83%的产率得到(2-Chloro-ethyl)-carbamic acid 5,10-dioxo-5,10-dihydro-pyrido[3,2-g]quinolin-3-ylmethyl ester
  参考文献：
  名称：

  Synthesis and in vitro evaluation of 1,8-diazaanthraquinones bearing 3-dialkylaminomethyl or 3-(N-alkyl- or N-aryl)carbamoyloxymethyl substituent

  摘要：

  A series of 1,8-diazaanthraquinone derivatives carrying a 3-dialkylaminomethyl or a 3-(N-alkyl or aryl)carbamoyloxymethyl substituent was synthesised and their in vitro cytotoxic activities were evaluated against eight human cancer cell lines (HOP62, SK-OV-3, HCT-15, SF295, MCF7, SNU-354, KB-3-1 and KB-V-1). A number of compounds including 8c, 8d and 11c showed cytotoxic activity comparable to that of doxorubicin against all human cancer cell lines tested. The compounds 8c and 8d were 2100 times more potent than doxorubicin against HCT-15, MCF7 and SNU-354 cancer cell lines. Furthermore, these compounds retained considerable cytotoxic activity against the doxorubicin-resistant cell line KB-V-1, implying their therapeutic potential to treat doxorubicin-resistant tumours. These compounds inhibited topoisomerase II-mediated DNA relaxation in vitro, suggesting that this inhibitory effect be attributable to their cytotoxicity. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(03)00118-1
• 作为产物：
  描述：

  3-acetoxymethyl-1,8-diazaanthracene-9,10-dione 在 lithium hydroxide 作用下， 以 乙醇 为溶剂， 以79%的产率得到3-hydroxymethyl-1,8-diazaanthraquinone
  参考文献：
  名称：

  Synthesis and in vitro cytotoxicity of 3-substituted-1,8-diazaanthraquinones produced by Lewis-acid catalyzed hetero diels-alder reaction

  摘要：

  A hetero Diels-Alder reaction of quinoline-5,8-dione with 1-(N,N-dimethylamino)-3-methyl-1-aza-1,3-butadiene proceeded to give 3-methyl-1,8-diazaanthraquinone (100% regioselectivity) in the presence of Lewis-acid catalyst (ZnCl(2) or ZnBr(2)). Subsequent functionalizations of the benzylic methyl group resulted in the 1,8-diazaanthraquinone analogues as potential antitumor agents. The most active compound, 8, exhibited in vitro cytotoxic activity comparable to that of doxorubicin. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00543-5

文献信息

• Synthesis and in vitro evaluation of 1,8-diazaanthraquinones bearing 3-dialkylaminomethyl or 3-(N-alkyl- or N-aryl)carbamoyloxymethyl substituent
  作者：Heesoon Lee、Seung-Il Lee、Jungsook Cho、Sang Un Choi、Sung-Il Yang

  DOI：10.1016/s0223-5234(03)00118-1

  日期：2003.7

  A series of 1,8-diazaanthraquinone derivatives carrying a 3-dialkylaminomethyl or a 3-(N-alkyl or aryl)carbamoyloxymethyl substituent was synthesised and their in vitro cytotoxic activities were evaluated against eight human cancer cell lines (HOP62, SK-OV-3, HCT-15, SF295, MCF7, SNU-354, KB-3-1 and KB-V-1). A number of compounds including 8c, 8d and 11c showed cytotoxic activity comparable to that of doxorubicin against all human cancer cell lines tested. The compounds 8c and 8d were 2100 times more potent than doxorubicin against HCT-15, MCF7 and SNU-354 cancer cell lines. Furthermore, these compounds retained considerable cytotoxic activity against the doxorubicin-resistant cell line KB-V-1, implying their therapeutic potential to treat doxorubicin-resistant tumours. These compounds inhibited topoisomerase II-mediated DNA relaxation in vitro, suggesting that this inhibitory effect be attributable to their cytotoxicity. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.
• Synthesis and in vitro cytotoxicity of 3-substituted-1,8-diazaanthraquinones produced by Lewis-acid catalyzed hetero diels-alder reaction
  作者：Heesoon Lee、Seung-Il Lee、Sung-Il Yang

  DOI：10.1016/s0960-894x(98)00543-5

  日期：1998.11

  A hetero Diels-Alder reaction of quinoline-5,8-dione with 1-(N,N-dimethylamino)-3-methyl-1-aza-1,3-butadiene proceeded to give 3-methyl-1,8-diazaanthraquinone (100% regioselectivity) in the presence of Lewis-acid catalyst (ZnCl(2) or ZnBr(2)). Subsequent functionalizations of the benzylic methyl group resulted in the 1,8-diazaanthraquinone analogues as potential antitumor agents. The most active compound, 8, exhibited in vitro cytotoxic activity comparable to that of doxorubicin. (C) 1998 Elsevier Science Ltd. All rights reserved.