1-(1,4-dihydro-5,8-dimethoxy-1,4-dioxonaphthalen-6-yl)-4-methylpent-3-enyl 4-nitrobenzoate | 1314765-82-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(1,4-dihydro-5,8-dimethoxy-1,4-dioxonaphthalen-6-yl)-4-methylpent-3-enyl 4-nitrobenzoate
• 英文别名: [(1R)-1-(1,4-dimethoxy-5,8-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] 4-nitrobenzoate
• CAS: 1314765-82-6
• 化学式: C₂₅H₂₃NO₈
• 分子量: 465.46
• InChiKey: GWPRWVMCXXGBNI-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  125
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-(1,4-dihydro-5,8-dimethoxy-1,4-dioxonaphthalen-6-yl)-4-methylpent-3-enyl 4-nitrobenzoate 在 吡啶 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 生成 (R)-1-((5E,8E)-5,8-bis(hydroxyimino)-1,4-dimethoxy-5,8-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 4-nitrobenzoate
  参考文献：
  名称：

  Synthesis and evaluation of novel alkannin and shikonin oxime derivatives as potent antitumor agents

  摘要：

  A set of forty alkannin and shikonin oxime derivatives were firstly designed and synthesized. Their cytotoxicities against three kinds of tumor cells and a normal cell line were tested and compared with alkannin and shikonin. The cell-based investigation demonstrated that some oxime derivatives were more or comparatively effective to the lead compounds, especially their selective and excellent antitumor activities towards K562 cells with no toxicity in normal cells. We may conclude that oximate modification to the mother nucleus of alkannin and shikonin is an available approach to acquire potent antitumor agents.

  DOI：

  10.1016/j.bmcl.2014.07.012
• 作为产物：
  描述：

  紫草素 在 盐酸 、 4-二甲氨基吡啶 、 sodium dithionite 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 4.5h， 生成 1-(1,4-dihydro-5,8-dimethoxy-1,4-dioxonaphthalen-6-yl)-4-methylpent-3-enyl 4-nitrobenzoate
  参考文献：
  名称：

  5、8 - O-二甲基酰基紫草素衍生物的6-异构体的半合成和抗肿瘤活性

  摘要：

  我们最近发现5、8- O-二甲基酰基紫草素衍生物显示出对MCF-7的选择性，并且对正常细胞没有毒性。在此，从紫草素开始合成一系列相应的5、8 - O-二甲基酰基紫草素衍生物的6-异构体。细胞毒性的体外证据表明，大多数化合物比紫草素更具活性或与之相比，并保留了对MCF-7，MDA-MB-231的选择性，而在正常细胞中则无毒性。而且，位置异构体5p，6c的体内抗癌活性进一步表明5、8 - O的6个异构体-二甲基酰基紫草素衍生物比其相应的2-异构体更具活性。因此，我们可以得出结论，紫草素侧链连接到5,8-二甲氧基-1,4-萘醌的位置与抗肿瘤活性有关。

  DOI：

  10.1016/j.ejmech.2011.05.006

文献信息

• Synthesis and evaluation of novel alkannin and shikonin oxime derivatives as potent antitumor agents
  作者：Rubing Wang、Xu Zhang、Hualong Song、Shanshan Zhou、Shaoshun Li

  DOI：10.1016/j.bmcl.2014.07.012

  日期：2014.9

  A set of forty alkannin and shikonin oxime derivatives were firstly designed and synthesized. Their cytotoxicities against three kinds of tumor cells and a normal cell line were tested and compared with alkannin and shikonin. The cell-based investigation demonstrated that some oxime derivatives were more or comparatively effective to the lead compounds, especially their selective and excellent antitumor activities towards K562 cells with no toxicity in normal cells. We may conclude that oximate modification to the mother nucleus of alkannin and shikonin is an available approach to acquire potent antitumor agents.
• Semi-synthesis and antitumor activity of 6-isomers of 5, 8-O-dimethyl acylshikonin derivatives
  作者：Wen Zhou、Xu Zhang、Ling Xiao、Jing Ding、Quan-Hua Liu、Shao-Shun Li

  DOI：10.1016/j.ejmech.2011.05.006

  日期：2011.8

  that 6-isomers of 5, 8-O-dimethyl acylshikonin derivatives were more active than their corresponding 2-isomers. Thus, we may conclude that the position of the side chain of shikonin attached to 5,8-dimethoxy -1,4-naphthoquinone is associated with the antitumor activity.

  我们最近发现5、8- O-二甲基酰基紫草素衍生物显示出对MCF-7的选择性，并且对正常细胞没有毒性。在此，从紫草素开始合成一系列相应的5、8 - O-二甲基酰基紫草素衍生物的6-异构体。细胞毒性的体外证据表明，大多数化合物比紫草素更具活性或与之相比，并保留了对MCF-7，MDA-MB-231的选择性，而在正常细胞中则无毒性。而且，位置异构体5p，6c的体内抗癌活性进一步表明5、8 - O的6个异构体-二甲基酰基紫草素衍生物比其相应的2-异构体更具活性。因此，我们可以得出结论，紫草素侧链连接到5,8-二甲氧基-1,4-萘醌的位置与抗肿瘤活性有关。