2-methyl-1-{[4-methyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)pent-3-en-1-yl]sulfanyl}propan-1-one | 1055318-44-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-methyl-1-{[4-methyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)pent-3-en-1-yl]sulfanyl}propan-1-one
• 英文别名: S-1-(1,4,5,8-tetramethoxynaphthalen-7-yl)-4-methylpent-3-enyl 2-methylpropanethioate；S-[4-methyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)pent-3-enyl] 2-methylpropanethioate
• CAS: 1055318-44-9
• 化学式: C₂₄H₃₂O₅S
• 分子量: 432.581
• InChiKey: XXTWCBWZEPNYLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  2-methyl-1-{[4-methyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)pent-3-en-1-yl]sulfanyl}propan-1-one 在 ammonium cerium (IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.17h， 以39%的产率得到5,8-dimethoxy-6-{4-methyl-1-[(2-methylpropanoyl)sulfanyl]pent-3-en-1-yl}-1,4-dihydronaphthalene-1,4-dione
  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：

  4-methyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)pent-3-en-1-thiol 、 异丁酸 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90%的产率得到2-methyl-1-{[4-methyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)pent-3-en-1-yl]sulfanyl}propan-1-one
  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

文献信息

• Synthesis and antitumor activity of 6- and 2-(1-substituted-thio-4-methylpent-3-enyl)-5,8-dimethoxynaphthalene-1,4-diones
  作者：Li-Ming Zhao、Tian-Pei Xie、Yu-Qin He、De-Feng Xu、Shao-Shun Li

  DOI：10.1016/j.ejmech.2008.09.039

  日期：2009.4

  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.