5-嘧啶羧酸,1,4-二氢-6-甲基-2-(甲硫基)-4-(3-硝基苯基)-,1-甲基丙基酯 | 125734-90-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 5-嘧啶羧酸,1,4-二氢-6-甲基-2-(甲硫基)-4-(3-硝基苯基)-,1-甲基丙基酯
• 英文名称: Butan-2-yl 6-methyl-2-methylsulfanyl-4-(3-nitrophenyl)-1,4-dihydropyrimidine-5-carboxylate
• CAS: 125734-90-9
• 化学式: C₁₇H₂₁N₃O₄S
• 分子量: 363.437
• InChiKey: QXXZQMQZGXHZGR-UHFFFAOYSA-N

物化性质

• 沸点：
  485.6±55.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-嘧啶羧酸,1,4-二氢-6-甲基-2-(甲硫基)-4-(3-硝基苯基)-,1-甲基丙基酯 、 N-甲基-N-羟乙基苄胺 生成 3-O-[2-[benzyl(methyl)amino]ethyl] 5-O-butan-2-yl 6-methyl-2-methylsulfanyl-4-(3-nitrophenyl)-4H-pyrimidine-3,5-dicarboxylate
  参考文献：
  名称：

  ATWAL, KARNAIL;ROVNYAK, GEORGE C.

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(3-Nitrophenylmethylidene)-3-oxobutanoic acid, 1-methylpropyl ester 、 2-甲基-2-疏基硫酸脲 在 sodium acetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-嘧啶羧酸,1,4-二氢-6-甲基-2-(甲硫基)-4-(3-硝基苯基)-,1-甲基丙基酯
  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

• ATWAL, KARNAIL;ROVNYAK, GEORGE C.
  作者：ATWAL, KARNAIL、ROVNYAK, GEORGE C.

  DOI：——

  日期：——
• 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.