6-[2-(Trifluoromethoxy)phenyl]imidazo[2,1-b][1,3]thiazole-5-carbaldehyde | 1015756-76-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-[2-(Trifluoromethoxy)phenyl]imidazo[2,1-b][1,3]thiazole-5-carbaldehyde
• CAS: 1015756-76-9
• 化学式: C₁₃H₇F₃N₂O₂S
• 分子量: 312.272
• InChiKey: IGVDSWRBHMQTIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  71.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-[2-(Trifluoromethoxy)phenyl]imidazo[2,1-b][1,3]thiazole-5-carbaldehyde 、 乙酰乙酸甲酯 在 ammonium hydroxide 作用下， 以 异丙醇 为溶剂， 以12%的产率得到Dimethyl 2,6-dimethyl-4-[6-[2-(trifluoromethoxy)phenyl]imidazo[2,1-b][1,3]thiazol-5-yl]-1,4-dihydropyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Imidazo[2,1-b]thiazole System: A Scaffold Endowing Dihydropyridines with Selective Cardiodepressant Activity

  摘要：

  The synthesis, characterization, and functional in vitro assays in cardiac tissues and smooth muscle (vascular and nonvascular) of a number of 4-imidazo[2,1-b]thiazole-1,4-dihydropyridines are reported. The binding properties for the novel compounds have been investigated and the interaction with the binding site common to other aryl-dihydropyridines has been demonstrated. Interestingly, the novel 4-aryl-dihydropyridines are L-type calcium channel blockers with a peculiar pharmacological behavior. Indeed, the imidazo[2,1-b]thiazole system is found to confer to the dihydropyridine scaffold an inotropic and/or chronotropic cardiovascular activity with a high selectivity toward the nonvascular tissue. Finally, molecular modeling studies were undertaken for the most representative compounds with the aim of describing the binding properties of the new ligands at molecular level and to rationalize the found structure-activity relationship data. Due to the observed pharmacological behavior of our compounds, they might be promising agents for the treatment of specific cardiovascular pathologies such as cardiac hypertrophy and ischemia.

  DOI：

  10.1021/jm070681+
• 作为产物：
  描述：

  6-[2-(Trifluoromethoxy)phenyl]imidazo[2,1-b][1,3]thiazole 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 以 氯仿 为溶剂， 以65%的产率得到6-[2-(Trifluoromethoxy)phenyl]imidazo[2,1-b][1,3]thiazole-5-carbaldehyde
  参考文献：
  名称：

  Imidazo[2,1-b]thiazole System: A Scaffold Endowing Dihydropyridines with Selective Cardiodepressant Activity

  摘要：

  The synthesis, characterization, and functional in vitro assays in cardiac tissues and smooth muscle (vascular and nonvascular) of a number of 4-imidazo[2,1-b]thiazole-1,4-dihydropyridines are reported. The binding properties for the novel compounds have been investigated and the interaction with the binding site common to other aryl-dihydropyridines has been demonstrated. Interestingly, the novel 4-aryl-dihydropyridines are L-type calcium channel blockers with a peculiar pharmacological behavior. Indeed, the imidazo[2,1-b]thiazole system is found to confer to the dihydropyridine scaffold an inotropic and/or chronotropic cardiovascular activity with a high selectivity toward the nonvascular tissue. Finally, molecular modeling studies were undertaken for the most representative compounds with the aim of describing the binding properties of the new ligands at molecular level and to rationalize the found structure-activity relationship data. Due to the observed pharmacological behavior of our compounds, they might be promising agents for the treatment of specific cardiovascular pathologies such as cardiac hypertrophy and ischemia.

  DOI：

  10.1021/jm070681+

文献信息

• Imidazo[2,1-<i>b</i>]thiazole System: A Scaffold Endowing Dihydropyridines with Selective Cardiodepressant Activity
  作者：Roberta Budriesi、Pierfranco Ioan、Alessandra Locatelli、Sandro Cosconati、Alberto Leoni、Maria P. Ugenti、Aldo Andreani、Rosanna Di Toro、Andrea Bedini、Santi Spampinato、Luciana Marinelli、Ettore Novellino、Alberto Chiarini

  DOI：10.1021/jm070681+

  日期：2008.3.1

  The synthesis, characterization, and functional in vitro assays in cardiac tissues and smooth muscle (vascular and nonvascular) of a number of 4-imidazo[2,1-b]thiazole-1,4-dihydropyridines are reported. The binding properties for the novel compounds have been investigated and the interaction with the binding site common to other aryl-dihydropyridines has been demonstrated. Interestingly, the novel 4-aryl-dihydropyridines are L-type calcium channel blockers with a peculiar pharmacological behavior. Indeed, the imidazo[2,1-b]thiazole system is found to confer to the dihydropyridine scaffold an inotropic and/or chronotropic cardiovascular activity with a high selectivity toward the nonvascular tissue. Finally, molecular modeling studies were undertaken for the most representative compounds with the aim of describing the binding properties of the new ligands at molecular level and to rationalize the found structure-activity relationship data. Due to the observed pharmacological behavior of our compounds, they might be promising agents for the treatment of specific cardiovascular pathologies such as cardiac hypertrophy and ischemia.