5-[(4-chlorophenylamino)methylidene]-2-thioxo-dihydropyrimidine-4,6(1H,3H)-dione | 69791-24-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-[(4-chlorophenylamino)methylidene]-2-thioxo-dihydropyrimidine-4,6(1H,3H)-dione
• 英文别名: 5-(4-chloro-anilinomethylene)-2-thioxo-dihydro-pyrimidine-4,6-dione；5-[(4-chloroanilino)methylidene]-2-sulfanylidene-1,3-diazinane-4,6-dione
• CAS: 69791-24-8
• 化学式: C₁₁H₈ClN₃O₂S
• mdl: MFCD00576062
• 分子量: 281.722
• InChiKey: OHKMMSLPLRVBDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.17
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.23
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  对氯苯胺 、 5-dimethylaminomethylene-2-thiobarbituric acid 以 乙醇 为溶剂， 以38%的产率得到5-[(4-chlorophenylamino)methylidene]-2-thioxo-dihydropyrimidine-4,6(1H,3H)-dione
  参考文献：
  名称：

  New thiobarbituric acid scaffold-based small molecules: Synthesis, cytotoxicity, 2D-QSAR, pharmacophore modelling and in-silico ADME screening

  摘要：

  A series of twenty five new thiobarbituric acid derivatives, viz. 3a-h, 4-7, 8a-c, 9, 10a-c, 11 and 12a-d, were designed and synthesized as potential cytotoxic agents. In-vitro screening of the new compounds against the three human cancer cell lines Caco-2, HepG-2 and MCF-7 was performed to assess their intrinsic activity. Compound 12d exhibited potent sub-micromolar activity against HepG-2 and MCF-7 (IC50 = 0.07 and 0.08 mu M, respectively). In-silico pharmacophore modelling of this chemotype compounds disclosed a five features' pharmacophore model representing essential steric and electronic fingerprints essential for activity. Finally, a 2D-QSAR model was devised to quantitatively correlate the 2D molecular feature descriptors of this series of thiobarbiturates with their cytotoxic activity against MCF-7. Finally, in silico evaluation of the physicochemical and ADME properties of these derivatives was performed.

  DOI：

  10.1016/j.ejps.2019.01.023

文献信息

• New thiobarbituric acid scaffold-based small molecules: Synthesis, cytotoxicity, 2D-QSAR, pharmacophore modelling and in-silico ADME screening
  作者：Heba S.A. El-Zahabi、Maha M.A. Khalifa、Yomna M.H. Gado、Amel M. Farrag、Mahmoud M. Elaasser、Nesreen A. Safwat、Reham R. AbdelRaouf、Reem K. Arafa

  DOI：10.1016/j.ejps.2019.01.023

  日期：2019.3

  A series of twenty five new thiobarbituric acid derivatives, viz. 3a-h, 4-7, 8a-c, 9, 10a-c, 11 and 12a-d, were designed and synthesized as potential cytotoxic agents. In-vitro screening of the new compounds against the three human cancer cell lines Caco-2, HepG-2 and MCF-7 was performed to assess their intrinsic activity. Compound 12d exhibited potent sub-micromolar activity against HepG-2 and MCF-7 (IC50 = 0.07 and 0.08 mu M, respectively). In-silico pharmacophore modelling of this chemotype compounds disclosed a five features' pharmacophore model representing essential steric and electronic fingerprints essential for activity. Finally, a 2D-QSAR model was devised to quantitatively correlate the 2D molecular feature descriptors of this series of thiobarbiturates with their cytotoxic activity against MCF-7. Finally, in silico evaluation of the physicochemical and ADME properties of these derivatives was performed.