ethyl 4-(4-hydroxy-3,5-dimethoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate | 940809-75-6

• 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-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: ethyl 4-(4-hydroxy-3,5-dimethoxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 940809-75-6
• 化学式: C₁₆H₂₀N₂O₅S
• 分子量: 352.411
• InChiKey: LIQBFRRSDRQDNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 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：
  121
• 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 、 硫脲 、 丁香醛 在 1-butyl-3-(4-sulfobutyl)-1H-imidazol-3-ium chloride 作用下， 以 neat (no solvent) 为溶剂， 反应 0.17h， 以47%的产率得到ethyl 4-(4-hydroxy-3,5-dimethoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  离子液体辅助合成二氢嘧啶（thi）one Biginelli加合物及其抑制脲酶的机理†

  摘要：

  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

  DOI：

  10.1039/c9nj03556g

文献信息

• Urease Inhibitors of Agricultural Interest Inspired by Structures of Plant Phenolic Aldehydes
  作者：Lívia Horta、Yane Mota、Gisele Barbosa、Taniri Braga、Ivanildo Marriel、Ângelo de Fátima、Luzia Modolo

  DOI：10.21577/0103-5053.20160208

  日期：——

  The plant phenolic natural products (PNPs) protocatechuic aldehyde, syringaldehyde and vanillin were used as platforms for obtaining four urease inhibitors. Urea (urease substrate) or thiourea (urease inhibitor) core was added to the structure of newly synthesized compounds to provide inhibitors up to 230-fold more active than the PNPs they originated from. The PNP derivatives are mixed inhibitors with higher affinity to urease active site. Two compounds were as efficient as N-(butyl) thiophosphoric triamide (NBPT) toward soil. Overall, PNPs derivatives are promising urease inhibitors for use as additive in urea-based fertilizers formulations.
• 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