2-Dimethylamino-ethylselenol | 7161-72-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-Dimethylamino-ethylselenol
• 英文别名: NoName_1667；2-(dimethylamino)ethaneselenol
• CAS: 7161-72-0
• 化学式: C₄H₁₁NSe
• 分子量: 152.098
• InChiKey: DIIOWUSRPSUBTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.13
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-Dimethylamino-ethylselenol 、 p-[(Z)-1-phenyl-2-ferrocenyl-2-butenylidene]benzenone 生成 2-ferrocenyl-1-methyl-3-phenyl-1H-inden-6-ol
  参考文献：
  名称：

  Evidence for Targeting Thioredoxin Reductases with Ferrocenyl Quinone Methides. A Possible Molecular Basis for the Antiproliferative Effect of Hydroxyferrocifens on Cancer Cells

  摘要：

  Many anticancer compounds are strong inhibitors of thioredoxin reductases (TrxRs), selenoenzymes involved in cellular redox regulation. This study examined the effect of two hydroxyferrocifens (1, FcOH; 2, FcOHTAM) and of their corresponding quinone methides (QMs), 1-QM, and 2-QM, on these enzymes. In vitro, both QMs were more potent TrxR inhibitors (IC50 2.5 mu M) than the hydroxyferrocifens (IC50 15 mu M). This inhibition was due to a Michael addition of the penultimate selenocysteine residue of TrxRs to the QMs. In Jurkat cancer cells, both 2 and 2-QM inhibited TrxRs in the same proportion, leading to accumulation of oxidized forms of thioredoxin, while 1 and 1-QM were scarcely effective. This difference of behavior was ascribed to the competitive conversion of 1-QM to an inactive indene in protic medium. This set of experiments confirms for the first time the role played by ferrocenyl quinone methides on several biological targets and gives a molecular basis for these effects. It also highlights differences in the mechanisms of action of 1 and 2 in cancer cells.

  DOI：

  10.1021/jm5013165
• 作为产物：
  描述：

  bis[2-(dimethylamino)ethyl] diselenide 在 亚膦酸 作用下， 以 乙醇 为溶剂， 生成 2-Dimethylamino-ethylselenol
  参考文献：
  名称：

  Hypophosphorous Acid, a Novel Reagent for the Reduction of Diselenides and the Selenol-Catalyzed Reduction of Disulfides^1,2

  摘要：

  DOI：

  10.1021/jo01342a052

文献信息

• Methods in selenium chemistry. III. Reduction of diselenides with dithiothreitol
  作者：Wolfgang H. H. Guenther

  DOI：10.1021/jo01287a044

  日期：1967.12
• Yokoyama,A. et al., Chemical and pharmaceutical bulletin, 1971, vol. 19, p. 1089 - 1094
  作者：Yokoyama,A. et al.

  DOI：——

  日期：——
• Hypophosphorous Acid, a Novel Reagent for the Reduction of Diselenides and the Selenol-Catalyzed Reduction of Disulfides^1,2
  作者：Wolfgang H. H. Günther

  DOI：10.1021/jo01342a052

  日期：1966.4
• Evidence for Targeting Thioredoxin Reductases with Ferrocenyl Quinone Methides. A Possible Molecular Basis for the Antiproliferative Effect of Hydroxyferrocifens on Cancer Cells
  作者：Anna Citta、Alessandra Folda、Alberto Bindoli、Pascal Pigeon、Siden Top、Anne Vessières、Michèle Salmain、Gérard Jaouen、Maria Pia Rigobello

  DOI：10.1021/jm5013165

  日期：2014.11.13

  Many anticancer compounds are strong inhibitors of thioredoxin reductases (TrxRs), selenoenzymes involved in cellular redox regulation. This study examined the effect of two hydroxyferrocifens (1, FcOH; 2, FcOHTAM) and of their corresponding quinone methides (QMs), 1-QM, and 2-QM, on these enzymes. In vitro, both QMs were more potent TrxR inhibitors (IC50 2.5 mu M) than the hydroxyferrocifens (IC50 15 mu M). This inhibition was due to a Michael addition of the penultimate selenocysteine residue of TrxRs to the QMs. In Jurkat cancer cells, both 2 and 2-QM inhibited TrxRs in the same proportion, leading to accumulation of oxidized forms of thioredoxin, while 1 and 1-QM were scarcely effective. This difference of behavior was ascribed to the competitive conversion of 1-QM to an inactive indene in protic medium. This set of experiments confirms for the first time the role played by ferrocenyl quinone methides on several biological targets and gives a molecular basis for these effects. It also highlights differences in the mechanisms of action of 1 and 2 in cancer cells.