(±)-isopropyl 6-methyl-4-(thiophen-2-yl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate | 518982-84-8

• 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: (±)-isopropyl 6-methyl-4-(thiophen-2-yl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: Propan-2-yl 6-methyl-4-(thiophen-2-yl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate；propan-2-yl 6-methyl-2-sulfanylidene-4-thiophen-2-yl-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 518982-84-8
• 化学式: C₁₃H₁₆N₂O₂S₂
• 分子量: 296.414
• InChiKey: CORCKTORTRFHJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-噻吩甲醛 、 乙酰乙酸异丙酯 、 硫脲 在 zinc(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以76%的产率得到(±)-isopropyl 6-methyl-4-(thiophen-2-yl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  Discovery of 3,4-Dihydropyrimidin-2(1H)-ones As a Novel Class of Potent and Selective A_2B Adenosine Receptor Antagonists

  摘要：

  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.

  DOI：

  10.1021/ml400185v

文献信息

• 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