SYNTHESIS AND CALCIUM CHANNEL ANTAGONIST ACTIVITY OF NEW SYMMETRICAL AND ASYMMETRICAL 4-[2-CHLORO-2-(4-CHLORO-6-METHYL-2-OXO-2H-PYRAN-3-YL)VINYL]-SUBSTITUTED 1,4-DIHYDROPYRIDINES

New symmetrical 4-[2-chloro-2-(4-chloro-6-methyl-2-oxo-2H-pyran-3-yl)vinyl]-substituted 1,4-dihydropyridines were synthesized in moderate to good yields via the modified Hantzsch reaction of beta-dicarbonyl compounds with (Z)-3-chloro-3-(4-chloro-6-methyl-2-oxo-2H-pyran-3-yl) acrolein in the presence of an excess amount of NH4OAc. Also, the reaction of beta-dicarbonyl compounds with (Z)-3-chloro-3-(4-chloro-6-methyl-2-oxo-2H-pyran-3-yl)acrolein in the presence of enamino esters and ketones was performed, and asymmetrical 4-[2-chloro-2-(4-chloro-6-methyl-2-oxo-2H-pyran-3-yl)vinyl]-substituted 1,4-dihydropyridines were obtained in moderate to good yields at room temperature. The calcium channel blocking activity of these compounds was assessed. They demonstrated moderate to weak effects, although one compound had a comparable effect (IC50 = 1.40x10(-7) M) with respect to the reference drug Nifedipine.