S-(E)-1-(1,4,5,8-tetramethoxynaphthalen-7-yl)-4-methylpent-3-enyl but-2-enethioate | 1055318-43-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: S-(E)-1-(1,4,5,8-tetramethoxynaphthalen-7-yl)-4-methylpent-3-enyl but-2-enethioate
• 英文别名: S-[4-methyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)pent-3-enyl] (E)-but-2-enethioate
• CAS: 1055318-43-8
• 化学式: C₂₄H₃₀O₅S
• 分子量: 430.565
• InChiKey: UJNCHTLPHGIEDP-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  79.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  S-(E)-1-(1,4,5,8-tetramethoxynaphthalen-7-yl)-4-methylpent-3-enyl but-2-enethioate 在 ammonium cerium (IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.17h， 以43%的产率得到S-(2E)-1-(1,4-dihydro-5,8-dimethoxy-1,4-dioxonaphthalen-6-yl)-4-methylpent-3-enyl but-2-enethioate
  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
• 作为产物：
  描述：

  巴豆酸 、 4-methyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)pent-3-en-1-thiol 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， 反应 12.0h， 以87%的产率得到S-(E)-1-(1,4,5,8-tetramethoxynaphthalen-7-yl)-4-methylpent-3-enyl but-2-enethioate
  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