S-1-(1,4-dihydro-5,8-dimethoxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl 2-methoxybenzothioate | 1055318-77-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: S-1-(1,4-dihydro-5,8-dimethoxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl 2-methoxybenzothioate
• 英文别名: S-[1-(5,8-dimethoxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] 2-methoxybenzenecarbothioate
• CAS: 1055318-77-8
• 化学式: C₂₆H₂₆O₆S
• 分子量: 466.555
• InChiKey: LIAZFDGQRCZHKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-(1,4,5,8-tetramethoxynaphthalen-2-yl)-4-methylpent-3-enyl 2-methoxybenzothioate 在 ammonium cerium (IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.17h， 以36%的产率得到6-(1-(2-methoxybenzoylthio)-4-methylpent-3-enyl)-5,8-dimethoxy-1,4-naphthoquinone
  参考文献：
  名称：

  Synthesis and antitumor activity of 6- and 2-(1-substituted-thio-4-methylpent-3-enyl)-5,8-dimethoxynaphthalene-1,4-diones

  摘要：

  In an attempt to develop potent and selective antitumor agents, a series of 6- and 2-(1-substituted-thio-4-methylpent-3-enyl)-5,8-dimethoxynaphthalene-1,4-diones were designed and synthesized. The cytotoxicities of these compounds were evaluated in vitro against BEL-7402, HT-29 and SPC-A1 cell lines. The pharmacological results showed that most of the prepared compounds displayed the excellent selective cytotoxicity toward HT-29 cells. From the structure-activity relationships we may conclude that the introduction of a thioether functional group at the 1'-position in the side chain of shikonin is associated with an increase in cytotoxicity. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.09.039