(±)-ethyl 6-methyl-4-(thiophen-3-yl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate | 352701-09-8

• 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: (±)-ethyl 6-methyl-4-(thiophen-3-yl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: Ethyl 6-methyl-4-(3-thienyl)-2-thioxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate；ethyl 6-methyl-2-sulfanylidene-4-thiophen-3-yl-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 352701-09-8
• 化学式: C₁₂H₁₄N₂O₂S₂
• 分子量: 282.387
• InChiKey: XCPUCFQBORCGNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (±)-ethyl 6-methyl-4-(thiophen-3-yl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 、 苯硼酸 在 potassium phosphate 、 四(三苯基膦)钯 、 噻吩-2-甲酸亚铜(I) 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以57%的产率得到ethyl 4-methyl-2-phenyl-6-(thiophen-3-yl)pyrimidine-5-carboxylate
  参考文献：
  名称：

  脱硫硫酸化芳基化与伴随的氧化脱氢反应，可快速获得嘧啶衍生物

  摘要：

  该报告描述了在Pd / Cu催化体系下通过脱氢硫化碳-碳交叉偶联和伴随的氧化脱氢合成2-芳基嘧啶衍生物的级联反应方法。它可从一个范围广泛的3,4-二氢嘧啶-1 H -2-硫酮（DHPM）和芳基硼酸一步一步快速，通用地获得各种2-芳基嘧啶。

  DOI：

  10.1016/j.tet.2017.10.010
• 作为产物：
  描述：

  3-噻吩甲醛 、 乙酰乙酸乙酯 、 硫脲 在 2-噻吩硼酸 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以66%的产率得到(±)-ethyl 6-methyl-4-(thiophen-3-yl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  2-噻吩基硼酸催化3,4-二氢嘧啶-2-( 1H )-酮/硫酮的高效一锅合成

  摘要：

  描述了使用 2-噻吩基硼酸作为催化剂以良好至极好的收率合成 3,4-二氢嘧啶-2-(1H)-酮/硫酮的简单有效的一锅三组分缩合反应。

  DOI：

  10.3184/174751912x13318375421203

文献信息

• Structure based virtual screening-driven identification of monastrol as a potent urease inhibitor
  作者：Umer Rashid、Iram Batool、Abdul Wadood、Ajmal Khan、Zaheer ul-Haq、Muhammad Iqbal Chaudhary、Farzana Latif Ansari

  DOI：10.1016/j.jmgm.2013.04.006

  日期：2013.6

  Virtual screening uses computer based methods to discover new ligands on the basis of biological structures. Among all virtual screening methods structure based docking has received considerable attention. In an attempt to identify new ligands as urease inhibitors, structure-based virtual screening (SBVS) of an in-house database of 10,000 organic compounds was carried out. The X-ray crystallographic structure of Bacillus pasteurii (BP) in complex with acetohydroxamic acid (PDB Code 4UBP) was used as a protein structure. As a starting point, similar to 10,000 compounds of our in-house database were analyzed to check redundancy and the compounds found repeated were removed from the database. Finally 6993 compounds were docked into the active site of BP urease using GOLD and MOE-Dock software. A remarkable feature of this study was the identification of monastrol, a well-known KSP inhibitor already in clinical trials, as a novel urease inhibitor. The hits identified were further evaluated by molecular docking and on examination of the affinity predictions, twenty-seven analogs of monastrol were synthesized by a multicomponent Biginelli reaction followed by their in vitro screening as urease inhibitors. Finally twelve compounds were identified as new urease inhibitors. The excellent in vitro activity suggested that these compounds may serve as viable lead compounds for the treatment of urease related problems. (c) 2013 Elsevier Inc. All rights reserved.
• Discovery of 3,4-Dihydropyrimidin-2(1<i>H</i>)-ones As a Novel Class of Potent and Selective A_2B Adenosine Receptor Antagonists
  作者：Abel Crespo、Abdelaziz El Maatougui、Pierfrancesco Biagini、Jhonny Azuaje、Alberto Coelho、José Brea、María Isabel Loza、María Isabel Cadavid、Xerardo García-Mera、Hugo Gutiérrez-de-Terán、Eddy Sotelo

  DOI：10.1021/ml400185v

  日期：2013.11.14

  We describe the discovery and optimization of 3,4-dihydropyrimidin-2(1H)-ones as a novel family of (nonzanthine) A(2B) receptor antagonists that exhibit an unusually high selectivity profile. The Biginelli-based hit optimization process enabled a thoughtful exploration of the structure-activity and structure-selectivity relationships for this chemotype, enabling the identification of ligands that combine structural simplicity with excellent hA(2B) AdoR affinity and remarkable selectivity profiles.
• 3,4-Dihydropyrimidin-2(1<i>H</i>)-ones as Antagonists of the Human A_2B Adenosine Receptor: Optimization, Structure–Activity Relationship Studies, and Enantiospecific Recognition
  作者：María Majellaro、Willem Jespers、Abel Crespo、María J. Núñez、Silvia Novio、Jhonny Azuaje、Rubén Prieto-Díaz、Claudia Gioé、Belma Alispahic、José Brea、María I. Loza、Manuel Freire-Garabal、Carlota Garcia-Santiago、Carlos Rodríguez-García、Xerardo García-Mera、Olga Caamaño、Christian Fernandez-Masaguer、Javier F. Sardina、Angela Stefanachi、Abdelaziz El Maatougui、Ana Mallo-Abreu、Johan Åqvist、Hugo Gutiérrez-de-Terán、Eddy Sotelo

  DOI：10.1021/acs.jmedchem.0c01431

  日期：2021.1.14