4-[(4-acetylphenyl)amino]-3-nitrocoumarin

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-[(4-acetylphenyl)amino]-3-nitrocoumarin
• 英文别名: 4-[(4-acetylphenyl)amino]-3-nitro-2H-chromen-2-one；4-(4-acetylanilino)-3-nitrochromen-2-one
• 化学式: C₁₇H₁₂N₂O₅
• mdl: MFCD01872709
• 分子量: 324.293
• InChiKey: GYRICMOXRDZDFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-[(4-acetylphenyl)amino]-3-nitrocoumarin 在 溴 、 溶剂黄146 作用下， 反应 5.0h， 以95%的产率得到4-{[4-(2-bromoacetyl)phenyl]amino}-3-nitrocoumarin
  参考文献：
  名称：

  Synthesis, in vitro cytotoxicity activity against the human cervix carcinoma cell line and in silico computational predictions of new 4-arylamino-3-nitrocoumarin analogues

  摘要：

  A new series of 4-arylamino-3-nitrocoumarin analogues (4-18) have been synthesized and characterized by sophisticated spectroscopic techniques (H-1 NMR, C-13 NMR) and mass spectrometry. All the new synthesized compounds were evaluated for their in vitro cytotoxic activity against the human cervix carcinoma cell line (KB-3-1) using resazurin assay with (+)-griseofulvin as the positive control (IC50 = 19 mu M). Among them, thiazolidinylidene derivative 17a that bearing malononitrile unit displayed the best cytotoxic potency with IC50 value of 21 mu M. Also, in silico docking simulation studies were conducted on human DNA topoisomerase 1 (Top1) (PDB: 1T8I) to explore and interpret the interaction pattern between the selected compounds and target enzyme as well confirm the acquired cytotoxicity results. In addition to the above, in silico predictions of physicochemical properties, ADME (absorption, distribution, metabolism and excretion) parameters, oral toxicity and indication of toxicity targets were implemented for some title compounds. (C) 2019 Published by Elsevier B.V.

  DOI：

  10.1016/j.molstruc.2019.127047
• 作为产物：
  描述：

  4-羟基-3-硝基香豆素 在 三乙胺 、 三氯氧磷 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 4-[(4-acetylphenyl)amino]-3-nitrocoumarin
  参考文献：
  名称：

  Synthesis, in vitro cytotoxicity activity against the human cervix carcinoma cell line and in silico computational predictions of new 4-arylamino-3-nitrocoumarin analogues

  摘要：

  A new series of 4-arylamino-3-nitrocoumarin analogues (4-18) have been synthesized and characterized by sophisticated spectroscopic techniques (H-1 NMR, C-13 NMR) and mass spectrometry. All the new synthesized compounds were evaluated for their in vitro cytotoxic activity against the human cervix carcinoma cell line (KB-3-1) using resazurin assay with (+)-griseofulvin as the positive control (IC50 = 19 mu M). Among them, thiazolidinylidene derivative 17a that bearing malononitrile unit displayed the best cytotoxic potency with IC50 value of 21 mu M. Also, in silico docking simulation studies were conducted on human DNA topoisomerase 1 (Top1) (PDB: 1T8I) to explore and interpret the interaction pattern between the selected compounds and target enzyme as well confirm the acquired cytotoxicity results. In addition to the above, in silico predictions of physicochemical properties, ADME (absorption, distribution, metabolism and excretion) parameters, oral toxicity and indication of toxicity targets were implemented for some title compounds. (C) 2019 Published by Elsevier B.V.

  DOI：

  10.1016/j.molstruc.2019.127047

文献信息

• Synthesis, in vitro cytotoxicity activity against the human cervix carcinoma cell line and in silico computational predictions of new 4-arylamino-3-nitrocoumarin analogues
  作者：Ahmed H. Halawa、Essam M. Eliwa、Ahmed A. Hassan、Hesham S. Nassar、R.A. El-Eisawy、Mohamed Ismail、Marcel Frese、Mohamed Shaaban、Ahmed M. El-Agrody、Ahmed H. Bedair、Norbert Sewald

  DOI：10.1016/j.molstruc.2019.127047

  日期：2020.1

  A new series of 4-arylamino-3-nitrocoumarin analogues (4-18) have been synthesized and characterized by sophisticated spectroscopic techniques (H-1 NMR, C-13 NMR) and mass spectrometry. All the new synthesized compounds were evaluated for their in vitro cytotoxic activity against the human cervix carcinoma cell line (KB-3-1) using resazurin assay with (+)-griseofulvin as the positive control (IC50 = 19 mu M). Among them, thiazolidinylidene derivative 17a that bearing malononitrile unit displayed the best cytotoxic potency with IC50 value of 21 mu M. Also, in silico docking simulation studies were conducted on human DNA topoisomerase 1 (Top1) (PDB: 1T8I) to explore and interpret the interaction pattern between the selected compounds and target enzyme as well confirm the acquired cytotoxicity results. In addition to the above, in silico predictions of physicochemical properties, ADME (absorption, distribution, metabolism and excretion) parameters, oral toxicity and indication of toxicity targets were implemented for some title compounds. (C) 2019 Published by Elsevier B.V.