diethyl 2,6-dimethyl-4-(6-(4-(trifluoromethyl)phenyl)imidazo[2,1-b]thiazol-5-yl)-1,4-dihydropyridine-3,5-dicarboxylate | 1308398-18-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: diethyl 2,6-dimethyl-4-(6-(4-(trifluoromethyl)phenyl)imidazo[2,1-b]thiazol-5-yl)-1,4-dihydropyridine-3,5-dicarboxylate
• 英文别名: Diethyl 2,6-dimethyl-4-[6-[4-(trifluoromethyl)phenyl]imidazo[2,1-b][1,3]thiazol-5-yl]-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 1308398-18-6
• 化学式: C₂₅H₂₄F₃N₃O₄S
• 分子量: 519.544
• InChiKey: ANJOUUJMFGOCNW-UHFFFAOYSA-N

物化性质

• 密度：
  1.39±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2-溴-4'-(三氟甲基)苯乙酮 在 ammonium hydroxide 、 三氯氧磷 作用下， 以 氯仿 、 异丙醇 、 丙酮 为溶剂， 反应 5.0h， 生成 diethyl 2,6-dimethyl-4-(6-(4-(trifluoromethyl)phenyl)imidazo[2,1-b]thiazol-5-yl)-1,4-dihydropyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Cystic Fibrosis: A New Target for 4-Imidazo[2,1-b]thiazole-1,4-dihydropyridines

  摘要：

  The pharmacology of the cystic fibrosis transmembrane conductance regulator (CFTR) Cl- channel has attracted significant interest in recent years with the aim to search for rational new therapies for diseases caused by CFTR malfunction. Mutations that abolish the function of CFTR cause the life-threatening genetic disease cystic fibrosis (CF). The most common cause of CF is the deletion of phenylalanine 508 (Delta F508) in the CFTR chloride channel. Felodipine, nifedipine, and other antihypertensive 1,4-dihydropyridines (1,4-DHPs) that block L-type Ca2+ channels are also effective potentiators of CFTR gating, able to correct the defective activity of Delta F508 and other CFTR mutants (Mol. Pharmacol. 2005, 68, 1736). For this purpose, we evaluated the ability of the previously and newly synthesized 4-imidazo[2,1-b]thiazoles-1,4-dihydropyridines without vascular activity and inotropic and/or chronotropic cardiac effects (J. Med. Chem. 2008, 51, 1592) to enhance the activity of Delta F508-CFTR. Our studies indicate compounds 17, 18, 20, 21, 38, and 39 as 1,4-DHPs with an interesting profile of activity.

  DOI：

  10.1021/jm200199r