dimethyl 4-[4-(2-methoxy-2-oxoethoxy)phenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate | 936844-07-4

• 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-[4-(2-methoxy-2-oxoethoxy)phenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
• 英文别名: Dimethyl 4-[4-(2-methoxy-2-oxoethoxy)phenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-di-carboxylate
• CAS: 936844-07-4
• 化学式: C₂₀H₂₃NO₇
• 分子量: 389.405
• InChiKey: RPHRGOVQNBWOQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  四氢吡咯 、 dimethyl 4-[4-(2-methoxy-2-oxoethoxy)phenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate 反应 7.0h， 以45.45%的产率得到dimethyl 2,6-dimethyl-4-{4-[2-oxo-2-(pyrrolidin-1-yl)ethoxy]phenyl}-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-hydroxyphenyl)-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40.98%的产率得到dimethyl 4-[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

文献信息

• Synthesis of a New Series of 4-Aryl-1,4-Dihydropyridines with Calcium Channel Blocking and Vasodilatory Activity
  作者：Ranju Bansal、Priyanka Jain、Carmen Calle、Rosalia Carron、Karen Pemberton、Alan L. Harvey

  DOI：10.1007/s00044-011-9600-x

  日期：2012.6

  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.