2-(1-acetoxy-4-methylpentyl)-1,4,5,8-tetramethoxynaphthalene | 168153-77-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(1-acetoxy-4-methylpentyl)-1,4,5,8-tetramethoxynaphthalene
• 英文别名: [4-methyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)pentyl] acetate
• CAS: 168153-77-3
• 化学式: C₂₂H₃₀O₆
• 分子量: 390.477
• InChiKey: ULRAMRIEGJVJKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(1-acetoxy-4-methylpentyl)-1,4,5,8-tetramethoxynaphthalene 在 吡啶 、 ammonium cerium (IV) nitrate 、 盐酸羟胺 作用下， 以 乙醇 、 水 、 乙酸乙酯 为溶剂， 反应 24.13h， 生成
  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：

  1,4,5,8-tetramethoxynaphthalene 在 4-二甲氨基吡啶 、 碘 、 magnesium 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 2-(1-acetoxy-4-methylpentyl)-1,4,5,8-tetramethoxynaphthalene
  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

文献信息

• Process for preparing 5,8-dihydroxynaphthoquinone derivatives, novel
  申请人：Kuhnil Pharmaceutical Co., Ltd.

  公开号：US05696276A1

  公开（公告）日：1997-12-09

  5,8-dihydroxynaphthoquinone derivatives represented by the following general formula (IA): ##STR1## in which R.sup.1 represents alkyl or alkenyl, R.sup.2a represents alkyl or a group --C(O)R wherein R represents alkyl, alkenyl, aryl, aralkyl or aralkenyl, which can be substituted or unsubstituted with one or more halogen(s), and R.sup.3 represents hydrogen or alkyl, provided that when R.sup.2a is a group --C(O)R and R.sup.3 is hydrogen, R.sup.1 is other than 3-methyl-2-butenyl; and when R.sup.2a represents methyl and R.sup.3 independently represents hydrogen or methyl, R.sup.1 is other than 3-methylbutyl. Processes for preparing 5,8-dihydroxynaphthoquinone derivatives are also provided.

  以下是以如下通式（IA）表示的5,8-二羟基萘醌衍生物：##STR1## 其中，R1代表烷基或烯基，R2a代表烷基或基团--C（O）R，其中R代表烷基，烯基，芳基，芳基烷基或芳基烯基，可以带有一个或多个卤素的取代基或未取代基，而R3代表氢或烷基，但当R2a为基团--C（O）R且R3为氢时，R1不是3-甲基-2-丁烯基；当R2a代表甲基且R3独立地代表氢或甲基时，R1不是3-甲基丁基。还提供了制备5,8-二羟基萘醌衍生物的过程。
• PROCESS FOR PREPARING 5,8-DIHYDRONAPHTHOQUINONE DERIVATIVES, NOVEL 5,8-DIHYDRONAPHTHOQUINONE DERIVATIVES AND THEIR USE AS ANTICANCER AGENT
  申请人：KUHNIL PHARMACEUTICAL CO., LTD.

  公开号：EP0662073A1

  公开（公告）日：1995-07-12
• US5696276A
  申请人：——

  公开号：US5696276A

  公开（公告）日：1997-12-09
• [EN] PROCESS FOR PREPARING 5,8-DIHYDRONAPHTHOQUINONE DERIVATIVES, NOVEL 5,8-DIHYDRONAPHTHOQUINONE DERIVATIVES AND THEIR USE AS ANTICANCER AGENT<br/>[FR] PROCEDE DE PREPARATION DE DERIVES DU 5,8-DIHYDRONAPHTHOQUINONE, DE NOUVEAUX DERIVES DU 5,8-DIHYDRONAPHTHOQUINONE, ET LEUR UTILISATION COMME AGENT ANTICANCEREUX
  申请人：AHN, Byung, Zun

  公开号：WO1995002572A1

  公开（公告）日：1995-01-26

  (EN) The present invention relates to a process for preparing 5,8-dihydronaphthoquinone derivatives represented by general formula (I) in which R1 represents alkyl or alkenyl, R2 represents hydrogen, alkyl or a group -C(O)R wherein R represents alkyl, alkenyl, aryl, aralkyl or aralkenyl, which can be substituted or unsubstituted with one or more halogen atom(s), and R3 represents hydrogen or alkyl, characterized in that: (A) a compound having general formula (II) in which R1, R2 and R3 are defined as previously described and R4 represents alkyl, is oxidized with cerium(IV) ammonium nitrate in a suitable solvent, or (B) a compound having general formula (Ia) in which R1 and R2 are defined as previously described and R3a represents alkyl, is dealkylated to prepare a compound having general formula (Ib) in which R1 and R2 are defined as previously described, or (C) a compound having general formula (Ic) in which R1 and R3 are defined as previously described, is reacted with a compound of formula RCOOH wherein R is defined as previously described, in the presence of an organic base and dicyclohexylcarbodiimide to prepare a compound having general formula (Id) in which R1, R3 and R are defined as previously described. In addition, the present invention relates to a novel 5,8-dihydronaphthoquinone derivative of formula (I) wherein when R2a is hydrogen or a group -C(O)R and R3 is hydrogen, R1 is other than 3-methyl-2-butenyl; and when R2a and R3 independently of one another represent hydrogen or methyl, R1 is other than 3-methylbutyl, and its use as an anticancer agent.(FR) Cette invention concerne le procédé de préparation de dérivés du 5,8-dihydronaphthoquinone représentés par la formule générale (I) où R1 représente l'alkyl ou l'alkényl, R2 représente l'hydrogène, l'alkyl ou un groupe -C(O)R, R représentant à son tour l'alkyl, l'alkényl, l'aryl, l'aralkyl ou l'aralkényl dans la mesure où ils peuvent se substituer ou se désubstituer par rapport à un ou plusieurs atomes halogène, et R3 représente l'hydrogène ou l'alkyl. R3 est caractérisé de trois façons. Sa première caractéristique (A) est d'être un composé dont la formule générale (II) comporte les éléments R1, R2 et R3 tels que précédemment définis. Toutefois, R4 représentant l'alkyl est oxydé par le nitrate d'ammonium de cérium(IV) présent dans un solvant approprié. La seconde caractéristique (B) de R3 est d'être un composé dont la formule générale (Ia) comporte les éléments R1 et R2 tels que précédemment définis, R3a représentant l'alkyl étant toutefois désalkylisé pour préparer un composé dont la formule générale (Ib) comporte les éléments R1 and R2 tels que précédemment définis. La troisième caractéristique (C) de R3 est d'être un composé dont la formule générale (Ic) comporte les éléments R1 et R3 tels que précédemment définis, mais mis en réaction avec un composé dont la formule est RCOOH où R est défini tel que précédemment décrit, en présence d'une base organique et de dicyclohexylcarbodiimide destiné à préparer un composé dont la formule générale (Id) comporte les éléments R1 et R3 tels que précédemment définis. En outre, la présente invention porte sur un nouveau dérivé du 5,8-dihydronaphthoquinone dont la formule (I) comporte un élément R2a qui est de l'hydrogène ou un groupe -C(O)R et R3 un élément qui est de l'hydrogène, R1 étant différent du 3-méthyl-2-butényl; et lorsque R2a et R3 représentent indépendamment l'un de l'autre de l'hydrogène ou du méthyle, R1 est différent d'un 3-méthylbutyl, et il est d'utilisation anticancéreuse.
• 6-Substituted 1,4-Naphthoquinone Oxime Derivatives (III): Synthesis and Cytotoxic Evaluation
  作者：G. Huang、M. C. Liu、Q. Q. Meng、S. S. Li

  DOI：10.1134/s1070363218050316

  日期：2018.5

  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.