5-dimethylaminomethylene-2-thiobarbituric acid | 116931-01-2

• 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-dimethylaminomethylene-2-thiobarbituric acid
• 英文别名: 5-[(dimethylamino)methylidene]-2-thioxodihydropyrimidine-4,6(1H,3H)-dione；5-(dimethylaminomethylidene)-2-sulfanylidene-1,3-diazinane-4,6-dione
• CAS: 116931-01-2
• 化学式: C₇H₉N₃O₂S
• 分子量: 199.233
• InChiKey: MGBXJSQEAHCKES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.04
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  61.44
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-dimethylaminomethylene-2-thiobarbituric acid 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 N'-[(4,6-dioxo-2-thioxo-tetrahydropyrimidin-5(6H)-ylidene)methyl]benzohydrazide
  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
• 作为产物：
  描述：

  4,6-二羟基-2-巯基嘧啶 、 N,N-二甲基甲酰胺二甲基缩醛 在 哌啶 作用下， 以 苯 为溶剂， 反应 5.0h， 以95%的产率得到5-dimethylaminomethylene-2-thiobarbituric acid
  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

• Yousif, M. M.; Fadda, A. A.; Elmorsy, S. S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, p. 994 - 997
  作者：Yousif, M. M.、Fadda, A. A.、Elmorsy, S. S.、Hassan, H. M.

  DOI：——

  日期：——
• YOUSIF, M. M.;FADDA, A. A.;ELMORSY, S. S.;HASSAN, H. M., INDIAN J. CHEM., 26,(1987) N 10, 994-997
  作者：YOUSIF, M. M.、FADDA, A. A.、ELMORSY, S. S.、HASSAN, H. M.

  DOI：——

  日期：——