New triethylammonium 6-amino-4-aryl-3-carbamoyl-5-cyano-1,4-dihydropyridine-2-thiolates were prepared in good yields by ternary condensation of malononitrile, aldehydes and monothiomalonamide (3-amino-3-thioxopropanamide) in the presence of Et3N. The thiolates undergo S-alkylation under mild conditions to give new 1,4-dihydronicotinamides. Molecular docking studies were carried out in order to explore the interaction mechanism and to investigate suitable binding modes of the new compounds on the calcium channel proteins. Some of the compounds in experiments in silico were found to be more potent as calcium channel blockers than reference drug Nifedipine.
6-Amino-4-aryl-3-carbamoyl-5-cyano-1,4-dihydropyridine-2-thiolates: Synthesis, reactions and docking studies
Published: 14 November 2020 by MDPI in The 24th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis
Keywords: 1,4-dihydropyridines, calcium channel blockers, 3-amino-3-thioxopropanamide, heterocyclization