(E)-1-(5,8-dimethoxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-enyl 3-(3,4-dimethoxyphenyl)acrylate | 1261300-32-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-1-(5,8-dimethoxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-enyl 3-(3,4-dimethoxyphenyl)acrylate
• 英文别名: [(1R)-1-(5,8-dimethoxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] (E)-3-(3,4-dimethoxyphenyl)prop-2-enoate
• CAS: 1261300-32-6
• 化学式: C₂₉H₃₀O₈
• 分子量: 506.552
• InChiKey: OAWFPAVTPFZLCE-ZGQNHIEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3,4-二甲氧基肉酸酸 、 (R)-2-(1-hydroxy-4-methylpent-3-enyl)-5,8-dimethoxynaphthalene-1,4-dione 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， 以37.4%的产率得到(E)-1-(5,8-dimethoxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-enyl 3-(3,4-dimethoxyphenyl)acrylate
  参考文献：
  名称：

  Semi-synthesis and anti-tumor activity of 5,8-O-dimethyl acylshikonin derivatives

  摘要：

  A set of twenty-two 5,8-O-dimethyl acylshikonin derivatives were designed and synthesized starting from shikonin. The cell-based investigation demonstrated that these dimethylated derivatives were less active than or equally effective to shikonin. However, the selective cytotoxicities toward MCF-7 were found among these derivatives, together with no toxicity in the normal cell. Furthermore, compounds 3f, 3p, 3r were subjected to Km mice suffering from S-180 carcinoma subcutaneously, which possessed more potent than Fluorouracil, a typical anticancer drug used clinically. So we may conclude that the modification to the mother nucleus of shikonin via the methylation is an available approach to acquiring anti-tumor agents with higher selectivity and lower toxicity. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.09.068