3,5-Pyridinedicarboxylic acid,4-(2,3-dichlorophenyl)-2-[[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethoxy]methyl]-1,4-dihydro-6-methyl-, 3-ethyl 5-(2-methoxyethyl) ester | 103198-44-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 3,5-Pyridinedicarboxylic acid,4-(2,3-dichlorophenyl)-2-[[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethoxy]methyl]-1,4-dihydro-6-methyl-, 3-ethyl 5-(2-methoxyethyl) ester
• 英文别名: 4-(2,3-Dichloro-phenyl)-2-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethoxymethyl]-6-methyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-ethyl ester 5-(2-methoxy-ethyl) ester
• CAS: 103198-44-3
• 化学式: C₃₀H₃₀Cl₂N₂O₈
• 分子量: 617.483
• InChiKey: OPDAQABBMDAVMK-UHFFFAOYSA-N

物化性质

• 沸点：
  703.9±60.0 °C(Predicted)
• 密度：
  1.344±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.27
• 重原子数：
  42.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  120.47
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  3,5-Pyridinedicarboxylic acid,4-(2,3-dichlorophenyl)-2-[[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethoxy]methyl]-1,4-dihydro-6-methyl-, 3-ethyl 5-(2-methoxyethyl) ester 在 甲胺 作用下， 以 乙醇 为溶剂， 以87%的产率得到2-(2-Amino-ethoxymethyl)-4-(2,3-dichloro-phenyl)-6-methyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-ethyl ester 5-(2-methoxy-ethyl) ester
  参考文献：
  名称：

  Long-acting dihydropyridine calcium antagonists. 9. Structure activity relationships around amlodipine

  摘要：

  The preparation of a range of 1,4-dihydropyridine analogues of amlodipine has been undertaken and their calcium antagonist activities on rat aorta have been evaluated. Increasing the size of the C5 ester group dramatically reduces calcium antagonist activity, a trend which would be compatible with the carbonyl group of that ester binding to the DHP receptor. Amlodipine analogues with extended C3 ester substituents also have lower potency than amlodipine, possibly because of disruption of a favourable interaction between the protonated amino group on the 2-substituent and the DHP receptor. Replacement of the 6-methyl substituent in amlodipine by alkoxyalkyl groups or electron-withdrawing groups is also detrimental to calcium antagonist activity.

  DOI：

  10.1016/0223-5234(91)90132-7
• 作为产物：
  描述：

  乙酰乙酸甲氧乙酯 在 氨 作用下， 以 乙醇 为溶剂， 生成 3,5-Pyridinedicarboxylic acid,4-(2,3-dichlorophenyl)-2-[[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethoxy]methyl]-1,4-dihydro-6-methyl-, 3-ethyl 5-(2-methoxyethyl) ester
  参考文献：
  名称：

  Long-acting dihydropyridine calcium antagonists. 9. Structure activity relationships around amlodipine

  摘要：

  The preparation of a range of 1,4-dihydropyridine analogues of amlodipine has been undertaken and their calcium antagonist activities on rat aorta have been evaluated. Increasing the size of the C5 ester group dramatically reduces calcium antagonist activity, a trend which would be compatible with the carbonyl group of that ester binding to the DHP receptor. Amlodipine analogues with extended C3 ester substituents also have lower potency than amlodipine, possibly because of disruption of a favourable interaction between the protonated amino group on the 2-substituent and the DHP receptor. Replacement of the 6-methyl substituent in amlodipine by alkoxyalkyl groups or electron-withdrawing groups is also detrimental to calcium antagonist activity.

  DOI：

  10.1016/0223-5234(91)90132-7