2-(2-azidoethoxymethyl)-3,5-bis(ethoxycarbonyl)-6-carboxy-4-(2-chlorophenyl)-1,4-dihydropyridine | 140171-88-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(2-azidoethoxymethyl)-3,5-bis(ethoxycarbonyl)-6-carboxy-4-(2-chlorophenyl)-1,4-dihydropyridine
• CAS: 140171-88-6
• 化学式: C₂₁H₂₃ClN₄O₇
• 分子量: 478.889
• InChiKey: WRQJAQAEYRIAQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  33.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  159.92
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-(2-azidoethoxymethyl)-3,5-bis(ethoxycarbonyl)-6-carboxy-4-(2-chlorophenyl)-1,4-dihydropyridine 在 lithium aluminium tetrahydride 、 盐酸羟胺 、 sodium acetate 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 3.5h， 生成 2-(2-Azido-ethoxymethyl)-4-(2-chloro-phenyl)-6-(hydroxyimino-methyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl 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：

  乙基(2-叠氮基乙氧基)乙酰乙酸酯 在 sodium hydroxide 、 ammonium acetate 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 7.0h， 生成 2-(2-azidoethoxymethyl)-3,5-bis(ethoxycarbonyl)-6-carboxy-4-(2-chlorophenyl)-1,4-dihydropyridine
  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