ethyl 4-(4-hydroxy-3,5-dimethoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: ethyl 4-(4-hydroxy-3,5-dimethoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate
• 英文别名: ethyl 4-(4-hydroxy-3,5-dimethoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate；ethyl 4-(4-hydroxy-3,5-dimethoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
• 化学式: C₁₆H₂₀N₂O₆
• 分子量: 336.345
• InChiKey: ZTDWOMWGRFTPCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  106
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  乙酰乙酸乙酯 、 尿素 、 丁香醛 在 lithium chloride 、 copper dichloride 作用下， 以 乙醇 为溶剂， 以60%的产率得到ethyl 4-(4-hydroxy-3,5-dimethoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate
  参考文献：
  名称：

  Biginelli 反应的廉价方案

  摘要：

  摘要 报道了一种由氯化铜-氯化锂组合催化剂体系催化高产率一锅法合成 3,4-二氢嘧啶-2(1H)-酮的方法。#IICT通讯号码：020612。

  DOI：

  10.1081/scc-200025633

文献信息

• β-Cyclodextrin-assisted synthesis of Biginelli adducts under solvent-free conditions
  作者：Natália Aparecida Liberto、Sarah de Paiva Silva、Ângelo de Fátima、Sergio Antonio Fernandes

  DOI：10.1016/j.tet.2013.07.024

  日期：2013.9

  β-cyclodextrin as a solid catalyst for the solvent-free synthesis of various Biginelli adducts. The advantages of our protocol included the following: (i) a metal-free methodology; (ii) high yields; (iii) simple and efficient work-up procedures; (iv) improved results under solvent-free conditions. β-cyclodextrin-catalyzed the Biginelli reactions for various aldehydes, demonstrating that it is an efficient and eco-friendly

  使用β-环糊精作为固体催化剂开发了一种简单，绿色且高效的方法，用于各种Biginelli加合物的无溶剂合成。我们协议的优点包括：（i）无金属方法；（ii）高产；（iii）简单有效的后处理程序；（iv）在无溶剂条件下改善结果。β-环糊精催化了各种醛类的Biginelli反应，表明它是制备杂环化合物的一种高效且环保的催化剂。
• An Inexpensive Protocol for Biginelli Reaction
  作者：A. Manjula、B. Vittal Rao、Parvathi Neelakantan

  DOI：10.1081/scc-200025633

  日期：2004.1.1

  Abstract A one‐pot synthesis of the 3,4‐dihydropyrimidin‐2(1H)‐ones catalysed by cupric chloride–lithium chloride combination catalyst system in high yields is reported. #IICT communication number: 020612.

  摘要 报道了一种由氯化铜-氯化锂组合催化剂体系催化高产率一锅法合成 3,4-二氢嘧啶-2(1H)-酮的方法。#IICT通讯号码：020612。
• Free radical scavenging and antiproliferative properties of Biginelli adducts
  作者：Daniel L. da Silva、Fabiano S. Reis、Dandara R. Muniz、Ana Lúcia T.G. Ruiz、João E. de Carvalho、Adão A. Sabino、Luzia V. Modolo、Ângelo de Fátima

  DOI：10.1016/j.bmc.2012.02.036

  日期：2012.4

  A series of Biginelli adducts bearing different substituents at C-4 position were synthesized by using p-sulfonic acid calix[4] arene as a catalyst. The in vitro potential to scavenge reactive nitrogen/oxygen species (RNS and ROS) and the ability to inhibit cancer cells growth were then investigated. Four adducts were found to be potent scavengers of 2,2-diphenyl-1-picrylhydrazyl (RNS) and/or superoxide anion (ROS) radicals. The antiproliferative activity against cancer cells was disclosed for the first time for 16 monastrol analogs. The capacity of all compounds to inhibit cancer cells growth was dependent on the histological origin of cells, except for BA24, which was highly active against all cell lines. BA20 and BA33 were as potent as the reference drug doxorubicin against adriamycin-resistant ovarian and prostate cancer cells, respectively. These results highlight some monastrol analogs as lead compounds for the design of new free radical scavengers and anticancer agents. (C) 2012 Elsevier Ltd. All rights reserved.
• Ionic liquid-assisted synthesis of dihydropyrimidin(thi)one Biginelli adducts and investigation of their mechanism of urease inhibition
  作者：Taniris Cafiero Braga、Thamara Ferreira Silva、Thamilla Maria Silva Maciel、Edjan Carlos Dantas da Silva、Edeildo Ferreira da Silva-Júnior、Luzia Valentina Modolo、Isis Martins Figueiredo、Josué Carinhanha Caldas Santos、Thiago Mendonça de Aquino、Ângelo de Fátima

  DOI：10.1039/c9nj03556g

  日期：——

  Twenty-six Biginelli adducts were synthesized through an ionic liquid-assisted synthesis with up to 92% yield. Sixteen of these Biginelli adducts were then assayed to determine their antiureolytic activity against purified urease from jack beans. The substances BA7-S, BA9-S and BA11-S were shown to be as efficient inhibitors as hydroxyurea, a positive control used in in vitro screening assay against

  通过离子液体辅助合成法合成了26种Biginelli加合物，收率高达92％。然后分析这些Biginelli加合物中的16种，以确定它们对来自千斤顶豆的纯化脲酶的抗脲水解活性。物质BA7-S，BA9-S和BA11-S被证明是与羟基脲有效的抑制剂，羟基脲是用于体外抗脲酶筛选试验的阳性对照。荧光研究表明，BA7-S，BA9-S，BA11-S和BA5-S分别具有5.95、6.72、4.55和4.28 M -1的高结合常数，而BAS12-S无取代基的log K b = 2.16 M -1的值低 。另外，在最热力学上有利的BA5-S和BA7-S脲酶复合物中，相应的Biginelli加合物能够通过非离子相互作用（例如疏水相互作用或氢和范德华相互作用）与脲酶的活性位点相互作用， 分别。计算机分析研究还支持BA与活性位点相互作用，从而证实了荧光和动力学分析研究，这清楚表明BA5-S和BA7-S是竞争性抑制剂（K