6-(1-Hydroxy-ethyl)-5,8-dimethoxy-[1,4]naphthoquinone | 101847-88-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-(1-Hydroxy-ethyl)-5,8-dimethoxy-[1,4]naphthoquinone
• 英文别名: 6-(1-hydroxyethyl)-5,8-dimethoxynaphthalene-1,4-dione
• CAS: 101847-88-5
• 化学式: C₁₄H₁₄O₅
• 分子量: 262.262
• InChiKey: BHMJHXGPPDMKAQ-UHFFFAOYSA-N

物化性质

• 沸点：
  482.0±45.0 °C(Predicted)
• 密度：
  1.300±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-(1-Hydroxy-ethyl)-5,8-dimethoxy-[1,4]naphthoquinone 在 吡啶 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以84%的产率得到C₁₄H₁₆N₂O₅
  参考文献：
  名称：

  6-Substituted 1,4-Naphthoquinone Oxime Derivatives (III): Synthesis and Cytotoxic Evaluation

  摘要：

  As a continuous study, a set of 23 new 6-substituted 1,4-naphthoquinone oxime derivatives are synthesized and screened for their in vitro cytotoxic activity. Four of those oxime derivatives demonstrate more potent cytotoxic activity towards K562, HCT-15, and HCT-116 cell lines than a reference drug 5-Fu. In particular, compound 21g exhibits the strongest inhibitory activity against K562 cell lines with IC50 values of 1.25 mu M. According to flow cytometry data, compound 21g can arrest cell cycle at S phase and induce a strong apoptotic response in K562 cells. The preliminary structure-activity relationship study shows that the nature of substituents in positions 6 and 1' of 1,4-naphthoquinone derivatives significantly affect their cytotoxic activity.

  DOI：

  10.1134/s1070363218050316
• 作为产物：
  描述：

  2-(1-hydroxyethyl)-1,4,5,8-tetramethoxynaphthalene 生成 6-(1-Hydroxy-ethyl)-5,8-dimethoxy-[1,4]naphthoquinone
  参考文献：
  名称：

  摘要：

  DOI：

文献信息

• The 2- or 6-(α-Hydroxyalkyl- and α-Oxoalkyl)-5,8-dimethoxy-1,4-naphthoquinones from the Oxidative Demethylation of 2-(α-Hydroxyalkyl- and α-Oxoalkyl)-1,4,5,8-tetramethoxynaphthalenes with Cerium(IV) Ammonium Nitrate, and the Further Demethylations to Naphthazarins
  作者：Yasuhiro Tanoue、Akira Terada

  DOI：10.1246/bcsj.61.2039

  日期：1988.6

  Oxidative demethylation of 2-(α-hydroxyalkyl- and α-oxoalkyl)-1,4,5,8-tetramethoxynaphthalene with (NH4)2Ce(NO3)6 gave two isomeric dimethoxynaphthoquinones: 2-substituted and 6-substituted 5,8-dimethoxy-1,4-naphthoquinones. Further demethylations of the former isomers to the corresponding dihydroxynaphthoquinones required an AgO–40%HNO3 reagent, while the latter isomers needed AlCl3 as the demethylation

  2-(α-羟烷基-和α-氧代烷基)-1,4,5,8-四甲氧基萘与 (NH4)2Ce(NO3)6 的氧化脱甲基得到两种异构二甲氧基萘醌：2-取代和 6-取代的 5,8-二甲氧基-1,4-萘醌。前者异构体进一步去甲基化为相应的二羟基萘醌需要 AgO–40%HNO3 试剂，而后者异构体需要 AlCl3 作为去甲基化试剂。给出了关于这些用 (NH4)2Ce(NO3)6 进行氧化去甲基化的机制的一些评论。
• Naphthazarin derivatives (VIII): Synthesis, inhibitory effect on DNA topoisomerase-I, and antiproliferative activity of 6-(1-acyloxyalkyl)-5,8-dimethoxy-1,4-naphthoquinones
  作者：Yong Kim、Young-Jae You、Byung-Zun Ahn

  DOI：10.1002/1521-4184(200110)334:10<318::aid-ardp318>3.0.co;2-8

  日期：2001.10

  6-(1-Acyloxyalkyl)-5,8-dimethoxy-1,4-naphthoquinone (DMNQ; 5,8-dimethoxy-1,4-naphthoquinone) derivatives were synthesized and examined for their inhibitory effect on DNA topoisomerase-I (Topo I) and their antiproliferative activity against L1210 cells. The Topo-I inhibitory effect of 6-(1-hydroxyalkyl)-DMNQ derivatives was found to be dependent on the size of the alkyl chains, suggesting that lipophilicity might be one important factor influencing the inhibitory effect. It was found that acylation of 6-(1-hydroxyalkyl)-DMNQ derivatives possessing alkyl chains of C2-C5 enhanced both bioactivities, suggesting that an increase of electrophilicity in the quinoid moiety makes the electrophilic arylation of bionucleophiles more favorable. It is noteworthy that 6-(1-heptanoyloxyethyl)-DMNQ exhibited both the most potent Topo I inhibitory activity (IC50, 11.5 microM) and the greatest antiproliferative activity (ED50, 0.05 microM) upon L1210 cells.
• TANOUE, YASUHIRO;TERADA, AKIRA, BULL. CHEM. SOC. JAP., 61,(1988) N 6, 2039-2045
  作者：TANOUE, YASUHIRO、TERADA, AKIRA

  DOI：——

  日期：——
• ——
  作者：XASIMOTO KINDZI、 GOTO KIETO、 TSUDA IOSIAKI

  DOI：——

  日期：——
• [EN] NOVEL 6-SUBSTITUTED-5,8-DIOXY-1,4-NAPHTHOQUINONE DERIVATIVES<br/>[FR] NOUVEAUX DERIVES 6-SUBSTITUE-5,8-DIOXY-1,4-NAPHTOQUINONE
  申请人：KUHNIL PHARMACEUTICAL CO., LTD.

  公开号：WO1997003940A1

  公开（公告）日：1997-02-06

  (EN) The present invention relates to a novel 6-substituted-5,8-dioxy-1,4-naphthoquinone derivative having formula (I), which is useful as an anticancer agent. In said formula, R1 represents alkyl; R2 represents hydrogen, alkyl or acyl; and R3 represents hydrogen or alkyl, and a process for preparing the same and an anti-cancer agent containing the compound (I) as an active ingredient.(FR) La présente invention se rapporte à un nouveau dérivé 6-substitué-5,8-dioxy-1,4-naphtoquinone, utile comme agent anticancéreux, ayant la formule générale (I) dans laquelle R1 représente alkyle; R2 représente hydrogène, alkyle ou acyle; et R3 représente hydrogène ou alkyle, et à son procédé de préparation, ainsi qu'à un agent anticancéreux contenant le composé (I) utilisé comme ingrédient actif.