1-(4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl)ethanone

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1-(4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl)ethanone
• 英文别名: 1-[1,2,3,4-tetrahydro-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-thioxo-5-pyrimidinyl]ethanone；5-acetyl-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-thione；1-[4-(4-Hydroxy-3-methoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl]ethanone；1-[4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidin-5-yl]ethanone
• 化学式: C₁₄H₁₆N₂O₃S
• 分子量: 292.359
• InChiKey: SRYLQLKNELDGEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  103
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  香草醛 、 硫脲 、 乙酰丙酮 在 Eu-Gd doped BiPO₄ nanocomposite 作用下， 以 neat (no solvent) 为溶剂， 以89 %的产率得到1-(4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl)ethanone
  参考文献：
  名称：

  Eu-Gd@BiPO4 纳米复合材料：Biginelli 反应中潜在的多相催化剂

  摘要：

  由于产物二氢嘧啶酮 (DHPM) 具有广泛的药理学重要性，Biginelli 反应在多组分反应中占有重要地位。在本工作中，在 5 mol% Eu-Gd@BiPO 纳米复合催化剂存在下，通过香草醛、1,3-二酮化合物和尿素的一步 Biginelli 缩合反应合成了香草醛的 DHPM 类似物。该非均相催化剂在 80 °C、无溶剂条件下，在 30 分钟的短时间内以高至优异的产率 (85-93%) 提供了所需的香草醛 DHPM 产物。由于纳米复合催化剂是非均相的，因此反应后很容易回收，并在 Biginelli 合成中重复使用 5 次，无需任何处理或显着的活性损失。筛选了合成的香草醛 DHPM 类似物的抗氧化和抗菌潜力。在 9 种化合物中，三种化合物 4e、4h 和 4i 在 DPPH 测定和还原力测定分析中分别显示出最大 %RSA 66.7%、67% 和 71%，而通过标准抗坏血酸。正如纸片扩散法所预测的，化合物

  DOI：

  10.1016/j.molliq.2023.122218

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。
• The Biginelli Reaction with an Imidazolium-Tagged Recyclable Iron Catalyst: Kinetics, Mechanism, and Antitumoral Activity
  作者：Luciana M. Ramos、Bruna C. Guido、Catharine C. Nobrega、José R. Corrêa、Rafael G. Silva、Heibbe C. B. de Oliveira、Alexandre F. Gomes、Fábio C. Gozzo、Brenno A. D. Neto

  DOI：10.1002/chem.201204314

  日期：2013.3.25

  The present work describes the synthesis, characterization, and application of a new ion‐tagged iron catalyst. The catalyst was employed in the Biginelli reaction with impressive performance. High yields have been achieved when the reaction was carried out in imidazolium‐based ionic liquids (BMI⋅PF6, BMI⋅NTf2, and BMI⋅BF4), thus showing that the ionic‐liquid effects play a role in the reaction. Moreover

  本工作描述了新型离子标记铁催化剂的合成，表征和应用。该催化剂用于Biginelli反应中，具有令人印象深刻的性能。当反应在咪唑鎓基的离子液体进行（BMI高的产率已经达到⋅ PF 6，BMI ⋅ NTF 2，和BMI ⋅ BF 4），因此表明离子液体效应在反应中起作用。此外，离子标记的催化剂可以回收并重复使用多达八次，而活性没有任何明显的损失。通过使用高分辨率电喷雾电离四极杆飞行时间质谱（HR-EI-QTOF）光谱和动力学实验进行的机理研究表明，只有一种反应途径可以排除发展条件下的其他两种可能性。理论计算符合所提出的铁催化剂的作用机理。最后，Biginelli反应的产物37种二氢嘧啶酮衍生物在针对MCF-7癌细胞线的测定中评估了其细胞毒性，并获得了令人鼓舞的结果，其中某些衍生物对健康细胞线（成纤维细胞）几乎无毒。
• Synthesis, conformational analysis and molecular docking studies on three novel dihydropyrimidine derivatives
  作者：Lóide O. Sallum、Wesley F. Vaz、Nádia M. Borges、Carlos E.M. de Campos、Adailton J. Bortoluzzi、Chris H.J. Franco、Luciana M. Ramos、Hamilton B. Napolitano

  DOI：10.1016/j.molstruc.2019.04.100

  日期：2019.9

  Abstract The dihydropyrimidine (DHPM) derivatives I, II and III were synthesized through Biginelli reaction and characterized by X-ray diffraction and vibrational spectroscopic analyses (Raman and FTIR), whereas a conformational study was conducted. The results show that the DHPM I, II and III belong to the triclinic and monoclinic systems. In a general way, the crystal structure of these compounds

  摘要 通过 Biginelli 反应合成了二氢嘧啶 (DHPM) 衍生物 I、II 和 III，并通过 X 射线衍射和振动光谱分析 (拉曼和 FTIR) 进行了表征，同时进行了构象研究。结果表明DHPM I、II和III属于三斜晶系和单斜晶系。一般来说，这些化合物的晶体结构通过 N-H⋯O、O-H⋯O 和 N-H⋯S 相互作用来稳定。C–H…π 和 π…π 接触使用 Hirshfeld 表面进行评估。为了评估 DHPM 组的电子特性，进行了使用 B3LYP/6-31G(d,p) 方法的理论计算。此外，还获得了这些化合物的计算红外光谱和一些全局反应性描述符、分子静电势图和前沿分子轨道能量。最后，
• Ultrasound-Mediated Synthesis of 3,4-Dihydropyrimidin-2-(<i>1H</i>)-Ones (or Thiones) with NaHSO₄·H₂O
  作者：Karim Akbari Dilmaghani、Behzad Zeynizadeh、Maryam Amirpoor

  DOI：10.1080/10426507.2013.777725

  日期：2013.11.1

  A fast and efficient Biginelli synthesis of 3,4-dihydropyrimidin-2-(1H)-ones (or thiones) by the reaction of aromatic aldehydes, -dicarbonyls, and urea/thiourea using NaHSO4H2O/ultrasound system is presented. The reactions were carried out in refluxing n-hexane/CH3CN (2.5:0.5mL) to afford the products in excellent yields.
• Evaluation of dihydropyrimidin-(2H)-one analogues and rhodanine derivatives as tyrosinase inhibitors
  作者：Jinbing Liu、Fengyan Wu、Lingjuan Chen、Jianming Hu、Liangzhong Zhao、Changhong Chen、Liwang Peng

  DOI：10.1016/j.bmcl.2011.02.076

  日期：2011.4

  A series of dihydropyrimidin-(2H)-one analogues and rhodanine derivatives were synthesized and their inhibitory effects on the diphenolase activity of mushroom tyrosinase were evaluated. The results showed that some of the synthesized compounds exhibited significant inhibitory activities. Especially, compound 15 bearing a hydroxyethoxyl group at position-4 of phenyl ring exhibited most potent tyrosinase inhibitory activity with IC50 value of 0.56 mM. The inhibition mechanism analysis of compound 15 demonstrated that the inhibitory effect of the compound on the tyrosinase was irreversible. These results suggested that such compounds might be served as lead compounds for further designing new potential tyrosinase inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.