2-hexanoyl-1,4,5,8-tetramethoxynaphthalene | 275803-04-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-hexanoyl-1,4,5,8-tetramethoxynaphthalene
• 英文别名: 1-(1,4,5,8-Tetramethoxynaphthalen-2-yl)hexan-1-one
• CAS: 275803-04-8
• 化学式: C₂₀H₂₆O₅
• 分子量: 346.423
• InChiKey: GLOLEYFXYUSJMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-hexanoyl-1,4,5,8-tetramethoxynaphthalene 在 吡啶 、 羟胺 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以84%的产率得到2-(1-hydroxyiminohexyl)-1,4,5,8-tetramethoxynaphthalene
  参考文献：
  名称：

  Naphthazarin Derivatives (VI): Synthesis, Inhibitory Effect on DNA Topoisomerase-I and Antiproliferative Activity of 2- or 6-(1-Oxyiminoalkyl)-5,8-dimethoxy-1,4-naphthoquinones

  摘要：

  2- or 6-(1-Hydroxyiminoalkyl)-5,8-dimethoxy-1,4-naphthoquinone (DMNQ) and 6-(1-propyloxyimino-alkyl)-DMNQ derivatives were synthesized. and their inhibitory effects on DNA topoisomerase-I (TOPO-I) and antiproliferative activities against L1210 cells were examined. In a comparison, it was found that 6-( 1 -hydroxyiminoalkyl)-DMNQ derivatives exhibited higher potencies in both bioactivities than 2-(1 -hydroxyiminoalkyl) -DMNQ analogues, suggesting that the difference in bioactivities between two positional isomers might be due to the steric hindrance of the side chain. It is noteworthy that the optimal size of alkyl group for both bioactivities of 6-(1 -hydroxyiminoalkyl)-DMNQ derivatives was pentyl to octyl (IC50, 22-29 mu M) for the inhibition of TOPO-I and propyl to nonyl (ED50, 0.12-0.19 mu M) for the antiproliferative activity. In addition, a similar potency of bioactivities was expressed by 6-( 1 -propyloxyiminoalkyl)-DMNQ derivatives, propylation products of the oximes.

  DOI：

  10.1002/(sici)1521-4184(20004)333:4<87::aid-ardp87>3.0.co;2-1
• 作为产物：
  描述：

  2-(1-hydroxyhexyl)-1,4,5,8-tetramethoxynaphthalene 在 manganese(IV) oxide 作用下， 以 苯 为溶剂， 反应 10.0h， 以85%的产率得到2-hexanoyl-1,4,5,8-tetramethoxynaphthalene
  参考文献：
  名称：

  Naththazarin衍生物（IV）：合成，抑制DNA拓扑异构酶I和2-或6-酰基-5,8-二甲氧基-1，4-萘醌的细胞毒性。

  摘要：

  合成了一些2-或6-酰基-5,8-二甲氧基-1,4-萘醌（DMNQ）衍生物，并评估了其对DNA拓扑异构酶I的抑制作用以及对L1210细胞的细胞毒性。与2-酰基-DMNQ衍生物相比，带有较高亲电醌部分的6-酰基-DMNQ化合物在抑制DNA拓扑异构酶I和细胞毒性方面显示出更高的效力，这暗示着亲电子芳基化可能参与了其生物活性。酶抑制的时间和温度依赖性表明芳基化不可逆地发生。在6-酰基-DMNQ衍生物中，具有中等大小（C（5）-C（9））的酰基的衍生物在生物活性方面比其他衍生物更高。此外，为了有效抑制DNA拓扑异构酶I，

  DOI：

  10.1016/s0223-5234(00)00129-x

文献信息

• Naphthazarin derivatives (IV): synthesis, inhibition of DNA topoisomerase I and cytotoxicity of 2- or 6-acyl-5,8-dimethoxy-1,4-naphthoquinones
  作者：Gyu-Yong Song、Yong Kim、Xiang-Guo Zheng、Young-Jae You、Hoon Cho、Jin-Ho Chung、Dai-Eun Sok、Byung-Zun Ahn

  DOI：10.1016/s0223-5234(00)00129-x

  日期：2000.3

  Some 2- or 6-acyl-5,8-dimethoxy-1,4-naphthoquinone (DMNQ) derivatives were synthesized and evaluated for inhibition of DNA topoisomerase I and cytotoxicity against L1210 cells. Compared with 2-acyl-DMNQ derivatives, 6-acyl-DMNQ compounds, bearing a higher electrophilic quinone moiety, showed a higher potency in the inhibition of DNA topoisomerase I and the cytotoxicity, implying the possible participation

  合成了一些2-或6-酰基-5,8-二甲氧基-1,4-萘醌（DMNQ）衍生物，并评估了其对DNA拓扑异构酶I的抑制作用以及对L1210细胞的细胞毒性。与2-酰基-DMNQ衍生物相比，带有较高亲电醌部分的6-酰基-DMNQ化合物在抑制DNA拓扑异构酶I和细胞毒性方面显示出更高的效力，这暗示着亲电子芳基化可能参与了其生物活性。酶抑制的时间和温度依赖性表明芳基化不可逆地发生。在6-酰基-DMNQ衍生物中，具有中等大小（C（5）-C（9））的酰基的衍生物在生物活性方面比其他衍生物更高。此外，为了有效抑制DNA拓扑异构酶I，
• Naphthazarin Derivatives (VI): Synthesis, Inhibitory Effect on DNA Topoisomerase-I and Antiproliferative Activity of 2- or 6-(1-Oxyiminoalkyl)-5,8-dimethoxy-1,4-naphthoquinones
  作者：Gyu-Yong Song、Yong Kim、Young-Jae You、Hoon Cho、Sung-Hoon Kim、Dai-Eun Sok、Byung-Zun Ahn

  DOI：10.1002/(sici)1521-4184(20004)333:4<87::aid-ardp87>3.0.co;2-1

  日期：2000.4

  2- or 6-(1-Hydroxyiminoalkyl)-5,8-dimethoxy-1,4-naphthoquinone (DMNQ) and 6-(1-propyloxyimino-alkyl)-DMNQ derivatives were synthesized. and their inhibitory effects on DNA topoisomerase-I (TOPO-I) and antiproliferative activities against L1210 cells were examined. In a comparison, it was found that 6-( 1 -hydroxyiminoalkyl)-DMNQ derivatives exhibited higher potencies in both bioactivities than 2-(1 -hydroxyiminoalkyl) -DMNQ analogues, suggesting that the difference in bioactivities between two positional isomers might be due to the steric hindrance of the side chain. It is noteworthy that the optimal size of alkyl group for both bioactivities of 6-(1 -hydroxyiminoalkyl)-DMNQ derivatives was pentyl to octyl (IC50, 22-29 mu M) for the inhibition of TOPO-I and propyl to nonyl (ED50, 0.12-0.19 mu M) for the antiproliferative activity. In addition, a similar potency of bioactivities was expressed by 6-( 1 -propyloxyiminoalkyl)-DMNQ derivatives, propylation products of the oximes.