2-[[(1,3-dimethyl-2,4,6-trioxotetrahydropyrimidin-5(2H)-ylidene)methyl]amino]benzoic acid | 1220909-84-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[[(1,3-dimethyl-2,4,6-trioxotetrahydropyrimidin-5(2H)-ylidene)methyl]amino]benzoic acid
• 英文别名: 2-((tetrahydro-1,3-dimethyl-2,4,6-trioxopyrimidin-5(6H)-ylidene)methyl)amino-benzoic acid；2-[(1,3-dimethyl-2,4,6-trioxo-1,3-diazinan-5-ylidene)methylamino]benzoic acid
• CAS: 1220909-84-1
• 化学式: C₁₄H₁₃N₃O₅
• 分子量: 303.274
• InChiKey: OSTWLUFBPLPBPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.73
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  107.02
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  邻氨基苯甲酸 、 6-hydroxy-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde 以 甲醇 为溶剂， 以78%的产率得到2-[[(1,3-dimethyl-2,4,6-trioxotetrahydropyrimidin-5(2H)-ylidene)methyl]amino]benzoic acid
  参考文献：
  名称：

  Synthesis of highly functionalized barbituric acids and study of their interactions with p-glycoprotein and Mg2+ – Potential candidates for multi drug resistance modulation

  摘要：

  A number of barbituric acids with appropriate substituent at C-5 position were synthesized and investigated for their interactions with p-gp and Mg2+. Compounds 5, 6, 8-10, 12-14 and 16 increased the basal activity of p-gp by more than 50% at 0.05 mu M concentration. Molecular docking indicate a number of H-bond interactions between these molecules and the amino acid residues of ATP binding site of p-gp. These molecules also showed appreciable interactions with Mg2+, an important component of efflux pump. All the results of these investigations favor the suitability of barbituric acids toward MDR modulation. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.12.033

文献信息

• Trisubstituted barbiturates and thiobarbiturates: Synthesis and biological evaluation as xanthine oxidase inhibitors, antioxidants, antibacterial and anti-proliferative agents
  作者：Joana Figueiredo、João L. Serrano、Eunice Cavalheiro、Leena Keurulainen、Jari Yli-Kauhaluoma、Vânia M. Moreira、Susana Ferreira、Fernanda C. Domingues、Samuel Silvestre、Paulo Almeida

  DOI：10.1016/j.ejmech.2017.11.070

  日期：2018.1

  acid derivatives have become progressively attractive to medicinal chemists due to their wide range of biological activities. Herein, different series of 1,3,5-trisubstituted barbiturates and thiobarbiturates were prepared in moderate to excellent yields and their activity as xanthine oxidase inhibitors, antioxidants, antibacterial agents and as anti-proliferative compounds was evaluated in vitro.

  由于其广泛的生物活性，巴比妥酸和硫代巴比妥酸衍生物已逐渐对药物化学家产生吸引力。本文中，以中等至优异的产率制备了不同系列的1,3,5-三取代的巴比妥酸酯和硫代巴比妥酸酯，并在体外评估了它们作为黄嘌呤氧化酶抑制剂，抗氧化剂，抗菌剂和抗增殖化合物的活性。发现有趣的生物活性巴比妥酸酯，即1,3-二甲基-5- [1-（2-（苯基肼基）亚乙基]嘧啶-2,4,6（1 H，3 H，5 H）-三酮（6c）和1， 3-二甲基-5- [1- [2-（4-硝基苯基）肼基]亚乙基]嘧啶-2,4,6（1 H，3 H，5H）-三酮（6e），其显示出同时发生的黄嘌呤氧化酶抑制作用（IC 50值分别为24.3和27.9μM）和2,2-二苯基-1-吡啶并肼基（DPPH）自由基清除活性（IC 50值为18.8）和23.8μM）。此外，5- [1-（2-苯基肼基）亚乙基]嘧啶-2,4,6（1 H，3 H，5 H）-三酮（6d）
• Synthesis of highly functionalized barbituric acids and study of their interactions with p-glycoprotein and Mg2+ – Potential candidates for multi drug resistance modulation
  作者：Palwinder Singh、Jatinder Kaur、Atul Bhardwaj

  DOI：10.1016/j.ejmech.2009.12.033

  日期：2010.3

  A number of barbituric acids with appropriate substituent at C-5 position were synthesized and investigated for their interactions with p-gp and Mg2+. Compounds 5, 6, 8-10, 12-14 and 16 increased the basal activity of p-gp by more than 50% at 0.05 mu M concentration. Molecular docking indicate a number of H-bond interactions between these molecules and the amino acid residues of ATP binding site of p-gp. These molecules also showed appreciable interactions with Mg2+, an important component of efflux pump. All the results of these investigations favor the suitability of barbituric acids toward MDR modulation. (C) 2009 Elsevier Masson SAS. All rights reserved.