dimethyl 1,4-dihydro-2,6-dimethyl-4-(5-benzofurazanyl)-3,5-pyridinedicarboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶二唑类
• 英文名称: dimethyl 1,4-dihydro-2,6-dimethyl-4-(5-benzofurazanyl)-3,5-pyridinedicarboxylate
• 英文别名: Dimethyl 4-(2,1,3-benzoxadiazol-5-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
• 化学式: C₁₇H₁₇N₃O₅
• 分子量: 343.339
• InChiKey: BHHJIBPCMXZLNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  5-溴甲基-2,1,3-苯并二唑 在 manganese(IV) oxide 、 水 、 三氟乙酸 、 calcium carbonate 作用下， 以 1,4-二氧六环 、 乙醇 、 氯仿 为溶剂， 反应 6.5h， 生成 dimethyl 1,4-dihydro-2,6-dimethyl-4-(5-benzofurazanyl)-3,5-pyridinedicarboxylate
  参考文献：
  名称：

  Benzofurazanyl- and benzofuroxanyl-1,4-dihydropyridines: synthesis, structure and calcium entry blocker activity

  摘要：

  The synthesis, structural characterization and calcium blocking activity of a series of benzofurazanyl-1,4-dihydropyridines (18 and 19) and benzofuroxanyl analogues (20 and 21) are reported. H-1-NMR showed that all the benzofuroxan derivatives exist in solution as tautomeric mixtures. The predominant tautomeric form in solution of the derivative 20 (dimethyl 1,4-dihydro-2,6-dimethyl-4-(4-benzofuroxanyl)-3,5-pyridinedicarboxylate) is also the one preferred in the solid state as shown by X-ray analysis. The conformation in the solid state of the benzofurazanyl analogue is also reported. Calcium entry blocker activity of the dihydropyridine derivatives 18-21 has been evaluated in isolated rabbit basilar artery as relaxation of calcium-induced contractions in high K+-depolarizing solution. All the compounds displayed high potency. The activity of benzofurazan derivatives was not changed by the N-oxidation. The two most active compounds 18 and 20 were as potent as Nifedipine.

  DOI：

  10.1016/s0223-5234(96)80001-8

文献信息

• Benzofurazanyl- and benzofuroxanyl-1,4-dihydropyridines: synthesis, structure and calcium entry blocker activity
  作者：AM Gasco、G Ermondi、R Fruttero、A Gasco

  DOI：10.1016/s0223-5234(96)80001-8

  日期：1996.1

  The synthesis, structural characterization and calcium blocking activity of a series of benzofurazanyl-1,4-dihydropyridines (18 and 19) and benzofuroxanyl analogues (20 and 21) are reported. H-1-NMR showed that all the benzofuroxan derivatives exist in solution as tautomeric mixtures. The predominant tautomeric form in solution of the derivative 20 (dimethyl 1,4-dihydro-2,6-dimethyl-4-(4-benzofuroxanyl)-3,5-pyridinedicarboxylate) is also the one preferred in the solid state as shown by X-ray analysis. The conformation in the solid state of the benzofurazanyl analogue is also reported. Calcium entry blocker activity of the dihydropyridine derivatives 18-21 has been evaluated in isolated rabbit basilar artery as relaxation of calcium-induced contractions in high K+-depolarizing solution. All the compounds displayed high potency. The activity of benzofurazan derivatives was not changed by the N-oxidation. The two most active compounds 18 and 20 were as potent as Nifedipine.