2-(3-Nitrophenylmethylidene)-3-oxobutanoic acid, 1-methylpropyl ester | 116679-99-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-(3-Nitrophenylmethylidene)-3-oxobutanoic acid, 1-methylpropyl ester
• 英文别名: butan-2-yl (2Z)-2-[(3-nitrophenyl)methylidene]-3-oxobutanoate
• CAS: 116679-99-3
• 化学式: C₁₅H₁₇NO₅
• 分子量: 291.304
• InChiKey: ZCCOXWRVSITTRJ-ZROIWOOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  哌啶 、 乙酰乙酸仲丁酯 、 间硝基苯甲醛 在 溶剂黄146 作用下， 以 水 、 乙酸乙酯 、 苯 为溶剂， 生成 2-(3-Nitrophenylmethylidene)-3-oxobutanoic acid, 1-methylpropyl ester
  参考文献：
  名称：

  Pyrimidinecarboxylic acid derivatives

  摘要：

  公开了化学式为##STR1##的吡啶化合物，其中R.sub.4是芳基或杂环烷基。这些化合物由于其钙通道阻滞血管扩张剂活性而可用作心血管药物。

  公开号：

  US04753946A1

文献信息

• US4237137A
  申请人：——

  公开号：US4237137A

  公开（公告）日：1980-12-02
• 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.
• Pyrimidinecarboxylic acid derivatives
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04753946A1

  公开（公告）日：1988-06-28

  Pyridine compounds of the formula ##STR1## wherein R.sub.4 is aryl or heterocyclo are disclosed. These compounds are useful as cardiovascular agents due to their calcium entry blocking vasodilator activity.

  公开了化学式为##STR1##的吡啶化合物，其中R.sub.4是芳基或杂环烷基。这些化合物由于其钙通道阻滞血管扩张剂活性而可用作心血管药物。