1-[4-(4-hydroxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]ethanone | 300820-11-5

• 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: 1-[4-(4-hydroxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]ethanone
• 英文别名: 1-(4-(4-hydroxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl)ethanone；5-acetyl-4-(4-hydroxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine；1-[4-(4-Hydroxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-5-pyrimidinyl]ethanone；1-[4-(4-hydroxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidin-5-yl]ethanone
• CAS: 300820-11-5
• 化学式: C₁₃H₁₄N₂O₂S
• 分子量: 262.332
• InChiKey: HXYWOOMRRCPRGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  93.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[4-(4-hydroxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]ethanone 在 sodium acetate 、 potassium carbonate 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 反应 44.0h， 生成 3-(4-chlorophenyl)-5-(4-[(dimethylamino)carbonyl]methoxyphenyl)-6-acetyl-7-methyl-5H-thiazolo[3,2-a]pyrimidine
  参考文献：
  名称：

  6-Acetyl-5H-thiazolo[3,2-a]pyrimidine Derivatives as the Novel Acetylcholinesterase Inhibitors: Design, Synthesis, and Biological Activity

  摘要：

  乙酰胆碱酯酶抑制剂是临床上最常用的抗阿尔茨海默药物。基于虚拟筛选方法，设计了一系列6-acetyl-5H-thiazolo[3,2-a]pyrimidine衍生物作为新型乙酰胆碱酯酶抑制剂。这些未在文献中报道的靶向化合物通过Biginelli反应和二氢嘧啶与取代苯乙酰氯的Hantzsch型缩合反应合成，并通过元素分析、红外光谱、质谱、1H-NMR和13C-NMR进行表征。针对人类乙酰胆碱酯酶的体外生物评价显示，大多数靶向化合物在10 µM时使用Ellman法表现出不同程度的抑制活性。这些结果为开发新药治疗阿尔茨海默疾病提供了一个起点，并为寻找具有新骨架的改进型乙酰胆碱酯酶抑制剂奠定了基础。初步的结构-活性关系表明，母核在C4位的苯环上的2-羟基乙氧基团在靶向化合物的AChE抑制活性中发挥了重要作用。

  DOI：

  10.2174/1573406411309050010
• 作为产物：
  描述：

  对羟基苯甲醛 、 硫脲 、 乙酰丙酮 反应 3.0h， 以73%的产率得到1-[4-(4-hydroxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]ethanone
  参考文献：
  名称：

  Synthesis of 5-Acyl-3,4-dihydropyrimidine-2-thiones via Solvent-Free, Solution-Phase and Solid-Phase Biginelli Procedures

  摘要：

  在使用或不使用催化剂的情况下，通过无溶剂 Biginelli 缩合反应获得了属于 5-酰基-3,4-二氢嘧啶-2-硫酮家族的化合物。一种前所未有的固相程序涉及聚合物支撑的醛，该程序允许从相应芳基酯的粗二酮开始，制备一系列 5-芳酰基衍生物。

  DOI：

  10.1055/s-0029-1217373

文献信息

• Oxalic acid as a versatile catalyst for one pot facile synthesis of 3,4-dihydropyrimidin-2-(1<i>H</i>)-ones and their thione analogues
  作者：Jaiprakash N. Sangshetti、Devanand B. Shinde、Nagnnath D. Kokare

  DOI：10.1002/jhet.5570450440

  日期：2008.7

  3,4-Dihydropyrimidin-2-(1H)-ones and their thione analogues are synthesized from the condensation of aromatic aldehydes, β-dicarbonyl compound and urea or thiourea in presence of 5 mol% of oxalic acid in ethanol-water (1:2; v/v) under mild reaction conditions. The yields obtained are better and also the use of very inexpensive catalyst, environmentally benign solvent and easy work-up are the advantageous

  3,4-二氢嘧啶-2-（1 H）-及其硫酮类似物是由芳香醛，β-二羰基化合物与脲或硫脲在乙醇水溶液中存在5 mol％的草酸缩合而成的（1 ：2; v / v）在温和的反应条件下。获得的产率更好，并且使用非常便宜的催化剂，对环境无害的溶剂和易于后处理是本方法的有利方面。
• Novel Dihydropyrimidine Derivatives And Their Use As Anti-Cancer Agents
  申请人：Lopez Roman

  公开号：US20080145453A1

  公开（公告）日：2008-06-19

  The invention concerns molecules of formula (I), drugs containing same and their use as anti-cancer agents.

  本发明涉及公式(I)的分子，含有该分子的药物以及它们作为抗癌剂的使用。
• 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.
• The Efficient Synthesis of 3,4-Dihydropyrimidin-2-(1<i>H</i>)-Ones and Their Sulfur Derivatives with H₂SO₄ Immobilized on Activated Charcoal
  作者：Karim Akbari Dilmaghani、Behzad Zeynizadeh、Hadi Parasajam

  DOI：10.1080/10426507.2011.631644

  日期：2012.4.1

  Various 3,4-dihydropyrimidin-2-(1H)-ones (DHPMs) and their sulfur derivatives were efficiently synthesized by a one-pot cyclocondensation reaction of aromatic and aliphatic aldehydes, beta-dicarbonyl compounds and urea (or thiourea) in the presence of sulfuric acid immobilized on activated charcoal (133% w/w). The reactions were carried out in refluxing n-hexane-acetonitrile (2.5:0.5 mL) within 5-150 min to give 3,4-dihydropyrimidinones (or thiones) in high to excellent yields (81-97%).