ethyl 4-(9,10-dioxo-9,10-dihydroanthracen-1-yl)-4-oxo-2-(2-(butylcarbamothioyl)hydrazono)butanoate | 1444103-03-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: ethyl 4-(9,10-dioxo-9,10-dihydroanthracen-1-yl)-4-oxo-2-(2-(butylcarbamothioyl)hydrazono)butanoate
• 英文别名: ethyl (2Z)-2-(butylcarbamothioylhydrazinylidene)-4-(9,10-dioxoanthracen-1-yl)-4-oxobutanoate
• CAS: 1444103-03-0
• 化学式: C₂₅H₂₅N₃O₅S
• 分子量: 479.557
• InChiKey: UTMOSSVFAWFNHK-DIBXZPPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  146
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-(蒽-1-基)乙酮 在 chromium(VI) oxide 、 sodium ethanolate 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 6.08h， 生成 ethyl 4-(9,10-dioxo-9,10-dihydroanthracen-1-yl)-4-oxo-2-(2-(butylcarbamothioyl)hydrazono)butanoate 、 ethyl 4-(9,10-dioxo-9,10-dihydroanthracen-1-yl)-4-oxo-2-(2-(butylcarbamothioyl)hydrazono)butanoate
  参考文献：
  名称：

  Synthesis, cytotoxic activity and DNA-interaction studies of novel anthraquinone–thiosemicarbazones with tautomerizable methylene group

  摘要：

  A series of novel anthraquinone thiosemicarbazone derivatives in a tautomerizable keto-imine form was synthesized and tested for their in vitro cytotoxic activity against human cancer cells (HeLa, MDA-MB-361, MDA-MB-453, K562, A549) and human normal MRC-5 cells. Several compounds efficiently inhibited cancer cell growth at micromolar concentrations, especially against K562 and HeLa cells. As determined by flow cytometric analysis, anthraquinone thiosemicarbazone caused significant increase in the number of sub-G1 phase of HeLa cells and apoptosis in a concentration-dependent manner. Also, inhibition of caspase-3, -8, and -9 with specific caspase inhibitors reduced the apoptosis mediated by the tested compounds in HeLa cells. All anthraquinone-thiosemicarbazones exhibit calf thymus DNA-binding activity, but no cleavage of plasmid DNA was observed. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.071

文献信息

• Synthesis, cytotoxic activity and DNA-interaction studies of novel anthraquinone–thiosemicarbazones with tautomerizable methylene group
  作者：Violeta Marković、Ana Janićijević、Tatjana Stanojković、Branka Kolundžija、Dušan Sladić、Miroslava Vujčić、Barbara Janović、Ljubinka Joksović、Predrag T. Djurdjević、Nina Todorović、Snežana Trifunović、Milan D. Joksović

  DOI：10.1016/j.ejmech.2013.03.071

  日期：2013.6

  A series of novel anthraquinone thiosemicarbazone derivatives in a tautomerizable keto-imine form was synthesized and tested for their in vitro cytotoxic activity against human cancer cells (HeLa, MDA-MB-361, MDA-MB-453, K562, A549) and human normal MRC-5 cells. Several compounds efficiently inhibited cancer cell growth at micromolar concentrations, especially against K562 and HeLa cells. As determined by flow cytometric analysis, anthraquinone thiosemicarbazone caused significant increase in the number of sub-G1 phase of HeLa cells and apoptosis in a concentration-dependent manner. Also, inhibition of caspase-3, -8, and -9 with specific caspase inhibitors reduced the apoptosis mediated by the tested compounds in HeLa cells. All anthraquinone-thiosemicarbazones exhibit calf thymus DNA-binding activity, but no cleavage of plasmid DNA was observed. (C) 2013 Elsevier Masson SAS. All rights reserved.