2-(propyloxyiminomethyl)-1,4,5,8-tetramethoxynaphthalene | 315701-76-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(propyloxyiminomethyl)-1,4,5,8-tetramethoxynaphthalene
• CAS: 315701-76-9
• 化学式: C₁₈H₂₃NO₅
• 分子量: 333.384
• InChiKey: BTZIYPAWUVCXCP-YBFXNURJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.63
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  58.51
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-(propyloxyiminomethyl)-1,4,5,8-tetramethoxynaphthalene 在 chromium(VI) oxide 、 硫酸 作用下， 以 水 、 丙酮 为溶剂， 以71%的产率得到1,4-Dimethoxy-5,8-dioxo-5,8-dihydro-naphthalene-2-carbaldehyde O-propyl-oxime
  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：

  1,4,5,8-四甲氧基萘-2-甲醛 在 吡啶 、 羟胺 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 20.0h， 生成 2-(propyloxyiminomethyl)-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

文献信息

• (E)-6-(1-alkyloxyiminoalkyl)-5,8-dimethoxy-1,4-naphthoquinones: synthesis, cytotoxic activity and antitumor activity
  作者：Young-Jae You、Yong Kim、Gyu-Yong Song、Byung-Zun Ahn

  DOI：10.1016/s0960-894x(00)00447-9

  日期：2000.10

  All of 13 (E)-6-(1-alkyloxyiminomethyl)-5,8-dimethoxy-1,4-naphthoquinone derivatives synthesized showed high ED,ED50 values, ranging from 0.1 to 0.3 mug/mL against L1210 cells. However, they were inactive on A549 cells. Nine compounds exhibited higher T/C (%) values (318-388%) than Adriamycin (T/C, 315%). (C) 2000 Elsevier Science Ltd. All rights reserved.