ethyl (6R,9bS)-8-methyl-5-oxo-6-(2-thienyl)-1,2,3,6,9,9bhexahydro-1H-imidazo[1',2':1,2]-pyrrolo[3,4-b]pyridine-7-carboxylate | 1581710-39-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: ethyl (6R,9bS)-8-methyl-5-oxo-6-(2-thienyl)-1,2,3,6,9,9bhexahydro-1H-imidazo[1',2':1,2]-pyrrolo[3,4-b]pyridine-7-carboxylate
• 英文别名: ethyl (2S,9R)-11-methyl-7-oxo-9-thiophen-2-yl-3,6,12-triazatricyclo[6.4.0.02,6]dodeca-1(8),10-diene-10-carboxylate
• CAS: 1581710-39-5
• 化学式: C₁₇H₁₉N₃O₃S
• 分子量: 345.422
• InChiKey: ZDGGLZLCHXAECR-WFASDCNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  98.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  乙二胺 、 diethyl (4S)-2-formyl-6-methyl-4-(thien-2'-yl)-1,4-dihydropyridine-3,5-dicarboxylate 在 potassium tert-butylate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以46%的产率得到ethyl (6R,9bS)-8-methyl-5-oxo-6-(2-thienyl)-1,2,3,6,9,9bhexahydro-1H-imidazo[1',2':1,2]-pyrrolo[3,4-b]pyridine-7-carboxylate
  参考文献：
  名称：

  Synthesis of novel chiral 1,4-dihydropyridinyl Schiff-base ligands, with characterization and evaluation of calcium channel blocker activity

  摘要：

  Treatment of 2-formyl-1,4-dihydropyridines with primary diamines gave rise to different products depending on the molar ratio of reactants. In the case of stoichiometric amounts of substrate and reactant, only tricyclic cis-diastereoisomer was obtained in yields ranging from 53 % up to 54 %. In addition, reaction of the above carboxaldehyde with primary diamines in a molar ratio of 2/1 resulted in the formation of bis-iminoderivatives in high yields of 80-97 %. All these compounds were examined as ligands for synthesis of complexes with metal salts. Ultimately, the selected compounds, in enantiopure and racemic form, were tested for their effect on both basal and agonist (or vanadate)-induced Ca-45(2+) influx.

  DOI：

  10.1007/s00706-014-1164-2

文献信息

• Synthesis of novel chiral 1,4-dihydropyridinyl Schiff-base ligands, with characterization and evaluation of calcium channel blocker activity
  作者：Štefan Marchalín、Dušan Valigura、Ľudovít Varečka、Boris Lakatoš、Monika Vaneková、Peter Baran、Ata Martin Lawson、Adam Daïch

  DOI：10.1007/s00706-014-1164-2

  日期：2014.5

  Treatment of 2-formyl-1,4-dihydropyridines with primary diamines gave rise to different products depending on the molar ratio of reactants. In the case of stoichiometric amounts of substrate and reactant, only tricyclic cis-diastereoisomer was obtained in yields ranging from 53 % up to 54 %. In addition, reaction of the above carboxaldehyde with primary diamines in a molar ratio of 2/1 resulted in the formation of bis-iminoderivatives in high yields of 80-97 %. All these compounds were examined as ligands for synthesis of complexes with metal salts. Ultimately, the selected compounds, in enantiopure and racemic form, were tested for their effect on both basal and agonist (or vanadate)-induced Ca-45(2+) influx.