2-(2-Dimethylamino-ethylsulfanyl)-6-methyl-4-(3-nitro-phenyl)-1,4-dihydro-pyrimidine-5-carboxylic acid isopropyl ester | 125734-85-2

• 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: 2-(2-Dimethylamino-ethylsulfanyl)-6-methyl-4-(3-nitro-phenyl)-1,4-dihydro-pyrimidine-5-carboxylic acid isopropyl ester
• 英文别名: Propan-2-yl 2-[2-(dimethylamino)ethylsulfanyl]-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyrimidine-5-carboxylate；propan-2-yl 2-[2-(dimethylamino)ethylsulfanyl]-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyrimidine-5-carboxylate
• CAS: 125734-85-2
• 化学式: C₁₉H₂₆N₄O₄S
• 分子量: 406.506
• InChiKey: UTWUFSNHYLOFDE-UHFFFAOYSA-N

物化性质

• 沸点：
  514.6±60.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (2-溴甲基)二甲胺 、 6-methyl-5-(isopropyloxyarbonyl)-4-(3-nitrophenyl)-3,4-dihydropyrimidin-2(1H)-thione 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 2-(2-Dimethylamino-ethylsulfanyl)-6-methyl-4-(3-nitro-phenyl)-1,4-dihydro-pyrimidine-5-carboxylic acid isopropyl ester
  参考文献：
  名称：

  Dihydropyrimidine calcium channel blockers: 2-heterosubstituted 4-aryl-1,4-dihydro-6-methyl-5-pyrimidinecarboxylic acid esters as potent mimics of dihydropyridines

  摘要：

  2-Heterosubstituted-4-aryl-1,4-dihydro-6-methyl-5-pyrimidinecar box ylic acid esters 8, which lack the potential CS symmetry of dihydropyridine calcium channel blockers, were prepared and evaluated for biological activity. Biological assays using potassium-depolarized rabbit aorta and radioligand binding techniques showed that some of these compounds are potent mimics of dihydropyridine calcium channel blockers. The combination of a branched ester (e.g. isopropyl, sec-butyl) and an alkylthio group (e.g. SMe) was found to be optimal for biological activity. When compared directly with similarly substituted 2-heteroalkyldihydropyridines 9, dihydropyrimidines 8 were found to be 30-fold less active. The solid-state structure of dihydropyrimidine analogue 8g shows that these compounds can adopt a molecular conformation which is similar to the reported conformation of dihydropyridine calcium channel blockers.

  DOI：

  10.1021/jm00167a035

文献信息

• Dihydropyrimidine calcium channel blockers: 2-heterosubstituted 4-aryl-1,4-dihydro-6-methyl-5-pyrimidinecarboxylic acid esters as potent mimics of dihydropyridines
  作者：Karnail S. Atwal、George C. Rovnyak、Joseph Schwartz、Suzanne Moreland、Anders Hedberg、Jack Z. Gougoutas、Mary F. Malley、David M. Floyd

  DOI：10.1021/jm00167a035

  日期：1990.5

  2-Heterosubstituted-4-aryl-1,4-dihydro-6-methyl-5-pyrimidinecar box ylic acid esters 8, which lack the potential CS symmetry of dihydropyridine calcium channel blockers, were prepared and evaluated for biological activity. Biological assays using potassium-depolarized rabbit aorta and radioligand binding techniques showed that some of these compounds are potent mimics of dihydropyridine calcium channel blockers. The combination of a branched ester (e.g. isopropyl, sec-butyl) and an alkylthio group (e.g. SMe) was found to be optimal for biological activity. When compared directly with similarly substituted 2-heteroalkyldihydropyridines 9, dihydropyrimidines 8 were found to be 30-fold less active. The solid-state structure of dihydropyrimidine analogue 8g shows that these compounds can adopt a molecular conformation which is similar to the reported conformation of dihydropyridine calcium channel blockers.