5-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)-3,4-dihydropyrimidin-2(1H)-one

• 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-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)-3,4-dihydropyrimidin-2(1H)-one
• 英文别名: 5-methoxycarbonyl-4-(3-nitrophenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one；methyl 6-methyl-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate；methyl 6-methyl-4-(3-nitrophenyl)-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
• 化学式: C₁₃H₁₃N₃O₅
• 分子量: 291.263
• InChiKey: VMFSQYFNNBSXEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(2-氯乙氧基)甲基]膦酸二乙酯 、 5-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)-3,4-dihydropyrimidin-2(1H)-one 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Design, synthesis, in silico, and in vitro evaluation of novel pyrimidine phosphonates with cytotoxicity against breast cancer cells

  摘要：

  Pyrimidine derivatives are widely used for the treatment of breast cancer and rapid efforts are contributing to develop highly potential novel molecules. In view of this, in this study, novel pyrimidine phosphonate molecules were designed so as to inhibit aromatase, a potential target of breast cancer. Quantitative structure activity relationship descriptors were defined and they revealed that the molecules have an effective and safer drug-like properties, which also supported by absorption, distribution, metabolism, and excretion study. Molecular docking of these compounds into the aromatase active site revealed that they are showing strong interaction forming H-bonds and arene cationic interactions. The ligand-receptor complex of compound 6i showed a best docking score of -15.776 kcal/mol among all. Hence, this compound was synthesized and tested in vitro at different concentrations of 25, 50, 100, and 200 mu g/mL against MDA-MB-231 adenocarcinoma breast cancer cells and it exhibited excellent antiproliferative activity and also induced apoptosis. The results from in silico structure activity relationships, molecular docking study and in vitro assays suggesting the compound as a potential source of chemotherapeutic drug for the treatment and management of breast cancer.

  DOI：

  10.1007/s00044-013-0628-y
• 作为产物：
  描述：

  间硝基苯甲醛 在 aluminum(III) nitrate nonahydrate 作用下， 反应 1.75h， 生成 5-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)-3,4-dihydropyrimidin-2(1H)-one
  参考文献：
  名称：

  硝酸铝九水合物（Al（NO3）3⋅9H2O）：一种由苄醇一锅法合成Biginelli化合物的高效氧化剂

  摘要：

  据报道，在存在铝的情况下，可以从伯芳基醇，β-酮酸酯，尿素或硫脲合成3,4-二氢嘧啶-2（1 H）-一或硫酮衍生物的清洁，高效的串联氧化环缩合工艺。 （NO 3）3 ⋅9ħ 2 O作为氧化剂催化剂（方案，表5）。

  DOI：

  10.1002/hlca.201100242

文献信息

• The development of an ecofriendly procedure for alkaline metal (II) sulfate promoted synthesis of<i>N</i>,<i>N</i>′-dimethyl substituted (unsubstituted)-4-aryl-3,4-dihydropyrimidones (thiones) and corresponding bis-analogues in aqueous medium: Evaluation by green chemistry metrics
  作者：Chhanda Mukhopadhyay、Arup Datta

  DOI：10.1002/jhet.283

  日期：——

  Different alkaline metal (II) sulfates were used as catalysts for the N,N′-dimethyl substituted as well as unsubstituted 4-aryl-3,4-dihydropyrimidones (thiones) and their corresponding bis-analogues in aqueous medium. Among the various salts, MgSO4·7H2O (Epsom salt) proved to be the best catalyst giving the desired products in good to excellent yields. This catalyst enables the construction of a series

  在水性介质中，将不同的碱金属（II）硫酸盐用作N，N'-二甲基取代的和未取代的4-芳基-3,4-二氢嘧啶酮（硫酮）及其相应的双类似物的催化剂。在各种盐中，MgSO 4 ·7H 2 O（泻盐）被证明是最好的催化剂，以良好至极佳的收率提供了所需的产物。该催化剂能够构建一系列化合物库，特别是对于N，N'-二甲基取代的DHPM，其合成在文献中非常罕见。通过绿色化学的应用评估了在多种底物上的反应指标和非常好的相关性。J.杂环化​​学.2010。
• Nebivolol nanoparticles: a first catalytic use in Biginelli and Biginelli-like reactions
  作者：Anamika Khaskel、Pranjit Barman、Subir Kumar Maiti、Utpal Jana

  DOI：10.1139/cjc-2017-0621

  日期：2018.12

  Herein, we report the catalytic activity of nebivolol nanoparticles a novel organocatalyst for the synthesis of DHPMs and DHPM-5-carboxamides. The nanoparticles are confirmed by DSC, TEM, AFM, and IR spectroscopy. The catalyst can be readily recovered and reused for the next four runs without any significant impact on the yields of the products. The products are fully characterized by FTIR, ¹H NMR, ¹³C NMR, and distortionless enhanced polarization transfer (DEPT) NMR. The methodology adopted here offers several advantages such as solvent-free reaction, low loading of catalyst, short reaction times, and quantifiable yields.

  在这里，我们报道了尼比地尔纳米颗粒作为合成DHPMs和DHPM-5-羧酰胺的新型有机催化剂的催化活性。通过DSC、TEM、AFM和IR光谱确认了这些纳米颗粒。该催化剂可以轻松回收并在接下来的四次运行中重复使用，对产物的产率没有显著影响。产物通过FTIR、1H NMR、13C NMR和无畸变增强极化转移（DEPT）NMR进行了全面表征。这里采用的方法具有多种优点，如免溶剂反应、催化剂负载量低、反应时间短和产率可量化。
• An Efficient Synthesis of 3,4-Dihydropyrimidin-2(1H)-Ones and Thiones Catalyzed by a Novel Brønsted Acidic Ionic Liquid under Solvent-Free Conditions
  作者：Yonghong Zhang、Bin Wang、Xiaomei Zhang、Jianbin Huang、Chenjiang Liu

  DOI：10.3390/molecules20033811

  日期：——

  report here an efficient and green method for Biginelli condensation reaction of aldehydes, β-ketoesters and urea or thiourea catalyzed by Brønsted acidic ionic liquid [Btto][p-TSA] under solvent-free conditions. Compared to the classical Biginelli reaction conditions, the present method has the advantages of giving good yields, short reaction times, near room temperature conditions and the avoidance

  我们在此报告了一种在无溶剂条件下由 Brønsted 酸性离子液体 [Btto][p-TSA] 催化的醛、β-酮酯和尿素或硫脲的 Biginelli 缩合反应的有效和绿色方法。与经典的 Biginelli 反应条件相比，本方法具有产率高、反应时间短、接近室温的条件以及避免使用有机溶剂和金属催化剂的优点。
• Design, Synthesis and Molecular Docking Studies of Some Tetrahydropyrimidine Derivatives as Possible Fascin Inhibitors
  作者：Narges Riahi、Amirhosein Kefayat、Ahmad Ghasemi、Mohammadhosein Asgarshamsi、Mojtaba Panjehpoor、Afshin Fassihi

  DOI：10.1002/cbdv.201800339

  日期：2019.2

  nifedipine in inhibiting the migration process. In silico studies proved 4h to be the most potent fascin inhibitor in terms of ΔGbind although it was not inhibiting migration. The controversy between the in vitro and in silico results may cancel the theory of the involvement of the fascin inhibition in the migration inhibition. However, the considerable antimigratory effects of some of the synthesized

  设计并制备了四氢嘧啶骨架的八种衍生物，它们是杂合化合物，具有莫纳斯特罗作为抗癌药和硝苯地平作为fascin阻断剂的结构特征。对所有化合物的细胞毒性效力以及抑制4T1乳腺癌细胞迁移的能力进行了评估。然后，使用分子对接模拟技术对它们在计算机上研究了抑制fascin蛋白的能力进行了研究。根据体外细胞毒性试验，最有效的化合物为4d，最弱的化合物为4a。相应的IC50值分别为193.70和248.75μm。根据分子对接结果，细胞毒性最小的化合物（4a）是与束缚纤维蛋白结合位点结合的最强化合物之一。4a和4e比其他化合物更好地抑制4T1细胞迁移。它们在抑制迁移过程方面比硝苯地平更有效。在计算机研究中，就ΔGbind而言，4h是最有效的fascin抑制剂，尽管它不抑制迁移。体外和计算机模拟结果之间的争议可能取消了fascin抑制作用与迁移抑制作用有关的理论。然而，一些合成化合物的显着的抗迁移作用鼓励进行
• An Efficient Synthesis of Multi-Substituted 3,4-Dihydropyrimidin-2(1H)-ones/thiones Under Solvent-Free Microwave Irradiation Using Alumina Sulfuric Acid
  作者：Hamid Reza Shaterian、Asghar Hosseinian、Majid Ghashang

  DOI：10.1080/10426500802083182

  日期：2008.12.23

  A new and efficient method for the synthesis of multi-substituted dihydropyrimidinone derivatives or their sulfur analogs has been developed under solvent-free microwave irradiation conditions in the presence of alumina sulfuric acid (Al2O3-SO3H) as an environmentally friendly heterogeneous recyclable catalyst, in high yields and short reaction time.

  在无溶剂微波辐射条件下，在硫酸铝 (Al2O3-SO3H) 作为环境友好的多相可回收催化剂存在下，开发了一种新的高效合成多取代二氢嘧啶酮衍生物或其硫类似物的方法。产率高，反应时间短。