3-(4-chlorophenyl)-1-(4-chlorophenylsulfonyl)quinazoline-2,4(1H,3H)-dione | 1228963-55-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-(4-chlorophenyl)-1-(4-chlorophenylsulfonyl)quinazoline-2,4(1H,3H)-dione
• 英文别名: 3-(4-Chlorophenyl)-1-(4-chlorophenyl)sulfonylquinazoline-2,4-dione
• CAS: 1228963-55-0
• 化学式: C₂₀H₁₂Cl₂N₂O₄S
• 分子量: 447.298
• InChiKey: WAHGOGZMJLTKCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-氯苯磺酰氯 、 3-(4-氯苯基)-1H-喹唑啉-2,4-二酮 在 sodium 、 叔丁醇 、 sodium hydroxide 作用下， 以 叔丁醇 、 水 为溶剂， 反应 6.5h， 以19%的产率得到3-(4-chlorophenyl)-1-(4-chlorophenylsulfonyl)quinazoline-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis and antitumor evaluation of novel cyclic arylsulfonylureas: ADME-T and pharmacophore prediction

  摘要：

  Novel derivatives of 5-(substituted)benzylidene-3-(4-substituted)phenylsulfonylimidazolidine-2,4-diones (3a-r), 1-(4-substituted)phenylsulfonyl-3-(4-substituted)phenylpyrimidine-2,4,6-(1H,3H,5H)-triones (6a-l), and 3-(4-substituted)phenyl-1-(4-substituted)phenylsulfonylquinazoline-2,4(1H,3H)-diones (8a-l) have been synthesized and tested for their antitumor activity against 60 tumor cell lines taken from 9 different organs. The tested compounds have showed good inhibitory effect at the ovarian cancer (IGROV1) cell line. A significant inhibition for (RXF393) renal cancer cells was observed with series 3 compounds, while in the other two series 6 and 8, there was a significant inhibition of ovarian cancer cells (OVCAR-8) and melanoma cells (SK-MEL-2). Interestingly, beside the strong inhibition of compound 3q to IGROV1 and RXF393 cells, a great inhibition (199 62%) for (M14) Melanoma cells was observed at the tested concentration (10 mu M) ADME-T and pharmacophore prediction methodology were used to study the antitumor activity of the most active compounds and to identify the structural features required for antitumor activity.

  DOI：

  10.1016/j.ejmech.2010.02.038

文献信息

• Synthesis and antitumor evaluation of novel cyclic arylsulfonylureas: ADME-T and pharmacophore prediction
  作者：Ibrahim M. El-Deeb、Said M. Bayoumi、Magda A. El-Sherbeny、Alaa A.-M. Abdel-Aziz

  DOI：10.1016/j.ejmech.2010.02.038

  日期：2010.6

  Novel derivatives of 5-(substituted)benzylidene-3-(4-substituted)phenylsulfonylimidazolidine-2,4-diones (3a-r), 1-(4-substituted)phenylsulfonyl-3-(4-substituted)phenylpyrimidine-2,4,6-(1H,3H,5H)-triones (6a-l), and 3-(4-substituted)phenyl-1-(4-substituted)phenylsulfonylquinazoline-2,4(1H,3H)-diones (8a-l) have been synthesized and tested for their antitumor activity against 60 tumor cell lines taken from 9 different organs. The tested compounds have showed good inhibitory effect at the ovarian cancer (IGROV1) cell line. A significant inhibition for (RXF393) renal cancer cells was observed with series 3 compounds, while in the other two series 6 and 8, there was a significant inhibition of ovarian cancer cells (OVCAR-8) and melanoma cells (SK-MEL-2). Interestingly, beside the strong inhibition of compound 3q to IGROV1 and RXF393 cells, a great inhibition (199 62%) for (M14) Melanoma cells was observed at the tested concentration (10 mu M) ADME-T and pharmacophore prediction methodology were used to study the antitumor activity of the most active compounds and to identify the structural features required for antitumor activity.