Benzyl 6-(3-(3-methyl-1,4-dihydronapthalen-2-ylselanyl)-2-(3-(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-ylthio)propanoyloxy)propanamido)hexanoate | 1416130-98-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Benzyl 6-(3-(3-methyl-1,4-dihydronapthalen-2-ylselanyl)-2-(3-(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-ylthio)propanoyloxy)propanamido)hexanoate
• 英文别名: benzyl 6-[[3-(3-methyl-1,4-dioxonaphthalen-2-yl)selanyl-2-[3-(3-methyl-1,4-dioxonaphthalen-2-yl)sulfanylpropanoyloxy]propanoyl]amino]hexanoate
• CAS: 1416130-98-7
• 化学式: C₄₁H₃₉NO₉SSe
• 分子量: 800.788
• InChiKey: UOKDORWDDUKASW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.27
• 重原子数：
  53
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  175
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  benzyl 6-isocyanohexanoate 、 2-(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-ylselanyl)acetaldehyde 、 維生素K-S(II) 以 水 为溶剂， 以73%的产率得到Benzyl 6-(3-(3-methyl-1,4-dihydronapthalen-2-ylselanyl)-2-(3-(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-ylthio)propanoyloxy)propanamido)hexanoate
  参考文献：
  名称：

  Novel peptidomimetic compounds containing redox active chalcogens and quinones as potential anticancer agents

  摘要：

  Many types of cancer cells are associated with a disturbed intracellular redox balance and oxidative stress (OS). Among the various agents employed to modulate the intracellular redox state of cells, certain redox catalysts containing quinone and chalcogen moieties have shown considerable promise. Passerini multicomponent reaction has been developed for the synthesis of agents combining two, three or even four redox centers in one molecule in a good yield. When incubated with cancer cells these agents inhibited cell proliferation and induced apoptotic cell death. Interestingly, some of these redox active compounds exhibited quite low toxicity with normal cells. The cause was obviously OS, which was reflected by significant decrease in reduced glutathione, subsequently cell cycle arrest and induction of apoptosis. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.09.033