7-methyl juglone acetate | 95636-28-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 7-methyl juglone acetate
• 英文别名: (3-Methyl-5,8-dioxo-1-naphthyl) acetate；(3-methyl-5,8-dioxonaphthalen-1-yl) acetate
• CAS: 95636-28-5
• 化学式: C₁₃H₁₀O₄
• 分子量: 230.22
• InChiKey: ZSQWAAHEKUTDPH-UHFFFAOYSA-N

物化性质

• 沸点：
  428.1±45.0 °C(Predicted)
• 密度：
  1.304±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-methyl juglone acetate 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以80%的产率得到7-甲基-5-羟基萘醌
  参考文献：
  名称：

  苯酚的合成：7-甲基methyl草酮和7,9,11三脱氧十二烷酮的制备

  摘要：

  芳基乙腈烯醇酸酯和不饱和酯的迈克尔加合物可以通过以下顺序转化为稠合酚醛系统：酯水解，Na / NH 3还原性氰化物的消除，Friedel-Crafts闭环和氧化。通过该脱核方法的线性多环系统的构建通过7-甲基胡格隆和dl-7,9，ll-三苯氧基十二烷二酮的区域特异性合成来说明。

  DOI：

  10.1016/s0040-4020(01)91540-6
• 作为产物：
  描述：

  4-(乙酰基氧基)-5,8-二甲氧基-2-萘羧酸乙酯 在 吡啶 、 lithium aluminium tetrahydride 、 ammonium cerium (IV) nitrate 、 palladium hydroxide, 20 wt% on carbon 、 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 50.0 ℃ 、101.33 kPa 条件下， 反应 6.17h， 生成 7-methyl juglone acetate
  参考文献：
  名称：

  7-甲基胡桃酮及其衍生物的区域选择性合成

  摘要：

  摘要 7-甲基胡桃酮作为一种天然存在的萘醌显示出惊人的抗菌、抗真菌、抗病毒和抗癌活性。其衍生物也被表征为制备天然萘醌和蒽醌的关键中间体。在本文中，我们报道7-甲基胡桃醌的区域选择性合成经由稠合多环系统的构建。该策略的关键步骤包括 2,5-二甲氧基苯甲醛与琥珀酸二乙酯的 Stobbe 缩合、分子内环化、还原、酸促进脱苄基化和进一步的硝酸铈 (IV) 铵介导的氧化。与文献报道的液氨中Birch条件或铝盐熔融热Friedel-Crafts环酰化的方法相比，新合成路线的反应条件温和，适合大规模制备。此外，合成中的所有原料都很容易获得。它对结构不对称萘醌衍生物的设计和合成具有重要意义。

  DOI：

  10.1080/14786419.2020.1761356

文献信息

• Activity of 7-methyljuglone derivatives against Mycobacterium tuberculosis and as subversive substrates for mycothiol disulfide reductase
  作者：Anita Mahapatra、Sannah P.N. Mativandlela、B. Binneman、P.B. Fourie、Chris J. Hamilton、J.J.M. Meyer、F. van der Kooy、Peter Houghton、Namrita Lall

  DOI：10.1016/j.bmc.2007.08.064

  日期：2007.12

  The naphthoquinone 7-methyljuglone (5-hydroxy-7-methyl-1,4-naphthoquinone) has previously been isolated and identified as an active component of root extracts of Euclea natalensis which displays antitubercular activity. Herein, a series of synthetic and plant-derived naphthoquinone derivates of the 7-methyljuglone scaffold have been prepared and evaluated for antibacterial activity against Mycobacterium tuberculosis. Several of these compounds have been shown to operate as subversive substrates with mycothiol disulfide reductase. The absence of a direct correlation between antitubercular activity and subversive substrate efficiency with mycothiol disulfide reductase, might be a consequence of their non-specific reactivity with multiple biological targets (e. g. other disulfide reductases). (c) 2007 Elsevier Ltd. All rights reserved.
• Cytotoxicity of synthesized 1,4-naphthoquinone analogues on selected human cancer cell lines
  作者：Navneet Kishore、Brigitte Binneman、Anita Mahapatra、Maryna van de Venter、Debbie du Plessis-Stoman、Gerhardt Boukes、Peter Houghton、J.J. Marion Meyer、Namrita Lall

  DOI：10.1016/j.bmc.2014.06.013

  日期：2014.9

  In an effort to establish new candidates with enhanced anticancer activity of 5-hydroxy-7-methyl-1,4-naphthoquinone scaffold (7-methyljuglone) previously isolated from the root extract of Euclea natalensis, a series of 7-methyljuglone derivatives have been synthesized and assessed for cytotoxicity on selected human cancer lines. These compounds were screened in vitro for anticancer activity on MCF-7, HeLa, SNO and DU145 human cancer cell lines by MTT assay. Most of them exhibited significant toxicity on cancer cell lines with lower IC50 values. The most potent derivative (19) exhibited the toxicity on HeLa and DU145 cell lines with IC50 value of 5.3 and 6.8μM followed by compound (5) with IC50 value of 10.1 and 9.3μM, respectively. Structure-activity relationship reveals that the fluoro substituents at position C-8 while hydroxyl substituents at C-2 and C-5 positions played an important role in toxicity.