[1-(tert-butylamino)-3-(3-methyl-1,4-dioxonaphthalen-2-yl)selanyl-1-oxopropan-2-yl] (2S)-3-(tert-butyldisulfanyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate | 1187664-40-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: [1-(tert-butylamino)-3-(3-methyl-1,4-dioxonaphthalen-2-yl)selanyl-1-oxopropan-2-yl] (2S)-3-(tert-butyldisulfanyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 1187664-40-9
• 化学式: C₃₀H₄₂N₂O₇S₂Se
• 分子量: 685.765
• InChiKey: APYDHYPYYCTZEQ-VQCQRNETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.36
• 重原子数：
  42
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  179
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  Boc-(S-tertBu)-Cys-OH 、 异氰酸叔丁酯 、 2-(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-ylselanyl)acetaldehyde 以 水 为溶剂， 以54%的产率得到[1-(tert-butylamino)-3-(3-methyl-1,4-dioxonaphthalen-2-yl)selanyl-1-oxopropan-2-yl] (2S)-3-(tert-butyldisulfanyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
  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

文献信息

• Novel peptidomimetic compounds containing redox active chalcogens and quinones as potential anticancer agents
  作者：Saad Shaaban、Randi Diestel、Bettina Hinkelmann、Yazh Muthukumar、Rajeshwar P. Verma、Florenz Sasse、Claus Jacob

  DOI：10.1016/j.ejmech.2012.09.033

  日期：2012.12

  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.