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

Journal of Medicinal Chemistry
2008.0

Abstract

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.

Knowledge Graph

Similar Paper

Imidazo[2,1-b]thiazole System: A Scaffold Endowing Dihydropyridines with Selective Cardiodepressant Activity
Journal of Medicinal Chemistry 2008.0
Ligand Based Approach to L-Type Calcium Channel by Imidazo[2,1-b]thiazole-1,4-Dihydropyridines: from Heart Activity to Brain Affinity
Journal of Medicinal Chemistry 2013.0
4-Imidazo[2,1-b]thiazole-1,4-DHPs and neuroprotection: preliminary study in hits searching
European Journal of Medicinal Chemistry 2019.0
Pyrrolo[2,1-c][1,4]benzothiazines: Synthesis, Structure-Activity Relationships, Molecular Modeling Studies, and Cardiovascular Activity
Journal of Medicinal Chemistry 1995.0
2-(2-Aryl-2-oxoethylidene)-1,2,3,4-tetrahydropyridines. Novel isomers of 1,4-dihydropyridine calcium channel blockers
Journal of Medicinal Chemistry 1988.0
Long-acting dihydropyridine calcium antagonists. 5. Synthesis and structure-activity relationships for a series of 2-[[(N-substituted-heterocyclyl)ethoxy]methyl]-1,4-dihydropyridine calcium antagonists
Journal of Medicinal Chemistry 1990.0
Synthesis of 3-[(2,3-dihydro-1,1,3-trioxo-1,2-benzisothiazol-2-yl)alkyl] 1,4-dihydropyridine-3,5-dicarboxylate derivatives as calcium channel modulators
Journal of Medicinal Chemistry 1992.0
Synthesis of a New Series of 4-Aryl-1,4-Dihydropyridines with Calcium Channel Blocking and Vasodilatory Activity
Medicinal Chemistry Research 2012.0
Cardiovascular Characterization of Pyrrolo[2,1-d][1,5]benzothiazepine Derivatives Binding Selectively to the Peripheral-Type Benzodiazepine Receptor (PBR):  From Dual PBR Affinity and Calcium Antagonist Activity to Novel and Selective Calcium Entry Blockers
Journal of Medicinal Chemistry 1996.0
Synthesis, molecular docking, and cardioprotective activity of 2-methylthio-1,4-dihydropyrimidines
Medicinal Chemistry Research 2012.0