Benzyl 6-(3-(3-methyl-1,4-dihydronaphthalen-2-ylselanyl)-2-(3-(phenylselanyl)propanoyloxy)propanamido)hexanoate | 1187664-39-6

• 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-dihydronaphthalen-2-ylselanyl)-2-(3-(phenylselanyl)propanoyloxy)propanamido)hexanoate
• 英文别名: benzyl 6-[[3-(3-methyl-1,4-dioxonaphthalen-2-yl)selanyl-2-(3-phenylselanylpropanoyloxy)propanoyl]amino]hexanoate
• CAS: 1187664-39-6
• 化学式: C₃₆H₃₇NO₇Se₂
• 分子量: 753.612
• InChiKey: AXOXQZPICBHFQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.63
• 重原子数：
  46
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  7

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 、 3-(phenylselanyl)propanoic acid 以 水 为溶剂， 以79%的产率得到Benzyl 6-(3-(3-methyl-1,4-dihydronaphthalen-2-ylselanyl)-2-(3-(phenylselanyl)propanoyloxy)propanamido)hexanoate
  参考文献：
  名称：

  Multicomponent reactions for the synthesis of multifunctional agents with activity against cancer cells

  摘要：

  多组分 Passerini 和 Ugi 反应能够快速高效地合成具有氧化还原作用的多功能硒和碲化合物，其中一些化合物对特定癌细胞具有相当强的细胞毒性。

  DOI：

  10.1039/b823149d

文献信息

• Multicomponent reactions for the synthesis of multifunctional agents with activity against cancer cells
  作者：Saad Shabaan、Lalla A. Ba、Muhammad Abbas、Torsten Burkholz、Annika Denkert、André Gohr、Ludger A. Wessjohann、Florenz Sasse、Wolfgang Weber、Claus Jacob

  DOI：10.1039/b823149d

  日期：——

  Multicomponent Passerini and Ugi reactions enable the fast and efficient synthesis of redox-active multifunctional selenium and tellurium compounds, of which some show considerable cytotoxicity against specific cancer cells.

  多组分 Passerini 和 Ugi 反应能够快速高效地合成具有氧化还原作用的多功能硒和碲化合物，其中一些化合物对特定癌细胞具有相当强的细胞毒性。
• 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.