2-(4-((4,6-dioxo-2-thioxotetrahydropyrimidin-5(2H)-ylidene)methyl)phenoxy)-N-(4-fluorophenyl)acetamide | 1022244-01-4

• 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: 2-(4-((4,6-dioxo-2-thioxotetrahydropyrimidin-5(2H)-ylidene)methyl)phenoxy)-N-(4-fluorophenyl)acetamide
• 英文别名: 2-(4-((4,6-dioxo-2-thioxotetrahydropyrimidin-5(6H)-ylidene)methyl)phenoxy)-N-(4-fluorophenyl)acetamide；2-[4-[(4,6-dioxo-2-sulfanylidene-1,3-diazinan-5-ylidene)methyl]phenoxy]-N-(4-fluorophenyl)acetamide
• CAS: 1022244-01-4
• 化学式: C₁₉H₁₄FN₃O₄S
• 分子量: 399.402
• InChiKey: HAAZBFZLRSIFNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  129
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-氯-4'-氟乙酰苯胺 在 potassium carbonate 、 potassium iodide 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 24.0h， 生成 2-(4-((4,6-dioxo-2-thioxotetrahydropyrimidin-5(2H)-ylidene)methyl)phenoxy)-N-(4-fluorophenyl)acetamide
  参考文献：
  名称：

  Synthesis and biological activity of novel barbituric and thiobarbituric acid derivatives against non-alcoholic fatty liver disease

  摘要：

  Forty-four barbituric acid or thiobarbituric acid derivatives were synthesized and evaluated for their effects on adipogenesis of 3T3-L1 adipocytes by measuring the expression of adiponectin in vitro. Four compounds (3a, 30, 3s, 4t) were found to increase the expression of adiponectin and lower the leptin level in 31341 adipocytes at respective concentration of 10 mu M. Among them, 3s showed the most efficacious. Oral administration of 3s effectively reduced body weight, liver weight, and visceral fat and regulated serum levels of biochemical markers in the high-fat/diet-induced Wistar rats. Histopathological evaluation of liver sections by Oil Red O and H&E staining confirmed 3s as a potent, orally active molecule for reducing fat deposition against non-alcoholic fatty liver disease. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.033

文献信息

• Novel (thio)barbituric-phenoxy-N-phenylacetamide derivatives as potent urease inhibitors: synthesis, in vitro urease inhibition, and in silico evaluations
  作者：Saeb Sedaghati、Homa Azizian、Mohammad Nazari Montazer、Maryam Mohammadi-Khanaposhtani、Mehdi Asadi、Fatemeh Moradkhani、Mehdi Shafiee Ardestani、Mohammad Sadegh Asgari、Azadeh Yahya-Meymandi、Mahmood Biglar、Bagher Larijani、Seyed Esmaeil Sadat-Ebrahimi、Alireza Foroumadi、Massoud Amanlou、Mohammad Mahdavi

  DOI：10.1007/s11224-020-01617-6

  日期：2021.2

  and evaluated against Helicobacter pylori urease. The latter assay revealed that all the synthesized compounds 7a-l (IC 50 = 0.69 ± 0.33–2.47 ± 0.23 μM) were significantly more potent than two used standard inhibitors, thiourea (IC 50 = 23 ± 0.73 μM) and hydroxyurea (IC 50 = 100 ± 1.7 μM). Docking study of the synthesized compounds demonstrated that these compounds as well fitted in the urease active

  合成了一系列新的（硫代）巴比妥酸-苯氧基-N-苯基乙酰胺衍生物 7a-1，并针对幽门螺杆菌脲酶进行了评估。后一种测定表明，所有合成的化合物 7a-l (IC 50 = 0.69 ± 0.33–2.47 ± 0.23 μM) 比两种使用的标准抑制剂硫脲 (IC 50 = 23 ± 0.73 μM) 和羟基脲 (IC 50 = 100 ± 1.7 μM）。对合成化合物的对接研究表明，这些化合物也适合脲酶活性位点。此外，对最有效化合物 7d 的分子动力学研究表明，该化合物与活性位点瓣残基 Cys592 和 His593 产生了重要的相互作用。此外，计算机药代动力学研究预测所有合成的化合物都是类似药物的。
• Synthesis and biological activity of novel barbituric and thiobarbituric acid derivatives against non-alcoholic fatty liver disease
  作者：Liang Ma、Shilin Li、Hao Zheng、Jinying Chen、Lin Lin、Xia Ye、Zhizhi Chen、Qinyuan Xu、Tao Chen、Jincheng Yang、Neng Qiu、Guangcheng Wang、Aihua Peng、Yi Ding、Yuquan Wei、Lijuan Chen

  DOI：10.1016/j.ejmech.2011.02.033

  日期：2011.6

  Forty-four barbituric acid or thiobarbituric acid derivatives were synthesized and evaluated for their effects on adipogenesis of 3T3-L1 adipocytes by measuring the expression of adiponectin in vitro. Four compounds (3a, 30, 3s, 4t) were found to increase the expression of adiponectin and lower the leptin level in 31341 adipocytes at respective concentration of 10 mu M. Among them, 3s showed the most efficacious. Oral administration of 3s effectively reduced body weight, liver weight, and visceral fat and regulated serum levels of biochemical markers in the high-fat/diet-induced Wistar rats. Histopathological evaluation of liver sections by Oil Red O and H&E staining confirmed 3s as a potent, orally active molecule for reducing fat deposition against non-alcoholic fatty liver disease. (C) 2011 Elsevier Masson SAS. All rights reserved.