6-(1-heptanoyloxypentyl)-5,8-dimethoxy-1,4-naphthoquinone

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-(1-heptanoyloxypentyl)-5,8-dimethoxy-1,4-naphthoquinone
• 英文别名: 1-(1,4-Dimethoxy-5,8-dioxonaphthalen-2-yl)pentyl heptanoate
• 化学式: C₂₄H₃₂O₆
• 分子量: 416.514
• InChiKey: NQXWRJJLUHEEKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  庚酸 、 6-(1-Hydroxy-pentyl)-5,8-dimethoxy-[1,4]naphthoquinone 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以42%的产率得到6-(1-heptanoyloxypentyl)-5,8-dimethoxy-1,4-naphthoquinone
  参考文献：
  名称：

  Naphthazarin derivatives (VIII): Synthesis, inhibitory effect on DNA topoisomerase-I, and antiproliferative activity of 6-(1-acyloxyalkyl)-5,8-dimethoxy-1,4-naphthoquinones

  摘要：

  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.

  DOI：

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

文献信息

• [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.
• 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.