dimethyl 4-[3-methoxy-4-(2-methoxy-2-oxoethoxy)phenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate | 1292811-75-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: dimethyl 4-[3-methoxy-4-(2-methoxy-2-oxoethoxy)phenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 1292811-75-6
• 化学式: C₂₁H₂₅NO₈
• 分子量: 419.431
• InChiKey: FLOKVMKWLVPHFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  四氢吡咯 、 dimethyl 4-[3-methoxy-4-(2-methoxy-2-oxoethoxy)phenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate 反应 7.0h， 以55.96%的产率得到dimethyl 4-{3-methoxy-4-[2-oxo-2-(pyrrolidin-1-yl)ethoxy]phenyl}-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Synthesis of a New Series of 4-Aryl-1,4-Dihydropyridines with Calcium Channel Blocking and Vasodilatory Activity

  摘要：

  Several new amide derivatives of 4-aryl-1,4-dihydropyridine carboxylic congeners have been synthesized in this study to obtain therapeutically useful compounds. The changes in pharmacological properties of dihydropyridines by the presence of polar groups at different positions of 4-phenyl substituent and also by introduction of unsymmetrical ester groups in the synthesized symmetrical analogs have been studied. In vitro calcium channel blocking activity has been evaluated in cultures of neonatal rat cortical neurons by measuring the inhibitory response at L-type calcium channels activated by veratridine. The newly synthesized dihydropyridines displayed moderate calcium channel blockade with IC50 values ranging from 2 to 10 mu M in comparison to nifedipine (IC50 = 57.7 nM). The vasodilatory activity was evaluated on isolated rat thoracic aortic rings precontracted by phenylephrine/KCl (30 mM). The symmetrically substituted dihydropyridine 8a exhibited maximum activity with IC50 = 0.64 mu M but was found to be approximately 24 times less active in comparison to standard drug nifedipine with IC50 = 27.5 nM.

  DOI：

  10.1007/s00044-011-9600-x
• 作为产物：
  描述：

  氯乙酸甲酯 、 dimethyl 4-(4-hydroxy-3-methoxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate 在 potassium carbonate 作用下， 以 丁酮 为溶剂， 反应 6.0h， 以66.66%的产率得到dimethyl 4-[3-methoxy-4-(2-methoxy-2-oxoethoxy)phenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Synthesis of a New Series of 4-Aryl-1,4-Dihydropyridines with Calcium Channel Blocking and Vasodilatory Activity

  摘要：

  Several new amide derivatives of 4-aryl-1,4-dihydropyridine carboxylic congeners have been synthesized in this study to obtain therapeutically useful compounds. The changes in pharmacological properties of dihydropyridines by the presence of polar groups at different positions of 4-phenyl substituent and also by introduction of unsymmetrical ester groups in the synthesized symmetrical analogs have been studied. In vitro calcium channel blocking activity has been evaluated in cultures of neonatal rat cortical neurons by measuring the inhibitory response at L-type calcium channels activated by veratridine. The newly synthesized dihydropyridines displayed moderate calcium channel blockade with IC50 values ranging from 2 to 10 mu M in comparison to nifedipine (IC50 = 57.7 nM). The vasodilatory activity was evaluated on isolated rat thoracic aortic rings precontracted by phenylephrine/KCl (30 mM). The symmetrically substituted dihydropyridine 8a exhibited maximum activity with IC50 = 0.64 mu M but was found to be approximately 24 times less active in comparison to standard drug nifedipine with IC50 = 27.5 nM.

  DOI：

  10.1007/s00044-011-9600-x