5-(hydrazinylmethylidene)-2-thioxo-dihydropyrimidine-4,6(1H,3H)-dione | 446830-07-5

• 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-(hydrazinylmethylidene)-2-thioxo-dihydropyrimidine-4,6(1H,3H)-dione
• 英文别名: 5-(hydrazinylmethylene)-2-thioxo-dihydropyrimidine-4,6(1H,5H)dione；5-(hydrazinylmethylidene)-2-sulfanylidene-1,3-diazinane-4,6-dione
• CAS: 446830-07-5
• 化学式: C₅H₆N₄O₂S
• 分子量: 186.194
• InChiKey: UTYALMREDMLJOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.14
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  96.25
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-(hydrazinylmethylidene)-2-thioxo-dihydropyrimidine-4,6(1H,3H)-dione 、 2,3-二甲氧基苯甲醛 以 乙醇 为溶剂， 以90%的产率得到5-[(2-(2,3-dimethoxybenzylidene)hydrazinyl)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
• 作为产物：
  描述：

  5-dimethylaminomethylene-2-thiobarbituric acid 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以93%的产率得到5-(hydrazinylmethylidene)-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

• Efficient one-pot preparation of novel fused chromeno[2,3-d]pyrimidine and pyrano[2,3-d]pyrimidine derivatives
  作者：Hala M. Aly、Mona M. Kamal

  DOI：10.1016/j.ejmech.2011.09.040

  日期：2012.1

  Some novel chromeno[2,3-d]pyrimidinone, pyrano[2,3-d]pyrimidine, dihydropyrimidine, pyridopyranopyrimidine and pyrimidopyranopyrimidine have been synthesized. The structures of target compounds were confirmed by elemental analyses and spectral data. The antimicrobial activity of all the target synthesized compounds were tested against various microorganismst such as Pseudomonas aeruginosa; Staphylococcus

  已经合成了一些新颖的铬诺[2,3- d ]嘧啶酮，吡喃并[2,3- d ]嘧啶，二氢嘧啶，吡啶并吡喃并嘧啶和嘧啶并吡喃并嘧啶。通过元素分析和光谱数据确认了目标化合物的结构。测试了所有目标合成化合物对各种微生物如铜绿假单胞菌（Pseudomonas aeruginosa）的抗菌活性; 金黄色葡萄球菌（细菌），黄曲霉（真菌）和白色念珠菌（酵母菌​​）采用圆盘扩散法。通常，新合成的化合物对前面提到的微生物显示出良好的抗菌活性。
• 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.