caa a22 4500 445875429 CHVBK 20180317145526.0 cr unu---uuuuu 170323e20110201xx s 000 0 eng 10.1007/s10593-011-0672-9 doi (NATIONALLICENCE)springer-10.1007/s10593-011-0672-9 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 [Elektronische Daten] [A. Shahrisa, M. Zirak, A. Mehdipour, R. Miri] New symmetrical 4-[2-chloro-2-(4-chloro-6-methyl-2-oxo-2H-pyran-3-yl)vinyl]-substituted 1,4-di-hydropyridines were synthesized in moderate to good yields via the modified Hantzsch reaction of β-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 β-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 =1.40×10−7 M) with respect to the reference drug Nifedipine. Springer Science+Business Media, Inc., 2011 calcium channel antagonist nationallicence dihydropyridines nationallicence 2-pyrone derivatives nationallicence Hantzsch reaction nationallicence Shahrisa A. Department of Organic and Biochemistry, Faculty of Chemistry, University of Tabriz, Tabriz, Iran aut Zirak M. Department of Organic and Biochemistry, Faculty of Chemistry, University of Tabriz, Tabriz, Iran aut Mehdipour A. Medicinal & Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shiraz, Iran aut Miri R. Medicinal & Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shiraz, Iran aut Chemistry of Heterocyclic Compounds Springer US; http://www.springer-ny.com 46/11(2011-02-01), 1354-1363 0009-3122 46:11<1354 2011 46 10593 https://doi.org/10.1007/s10593-011-0672-9 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s10593-011-0672-9 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Shahrisa A. Department of Organic and Biochemistry, Faculty of Chemistry, University of Tabriz, Tabriz, Iran aut NATIONALLICENCE 700 1- Zirak M. Department of Organic and Biochemistry, Faculty of Chemistry, University of Tabriz, Tabriz, Iran aut NATIONALLICENCE 700 1- Mehdipour A. Medicinal & Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shiraz, Iran aut NATIONALLICENCE 700 1- Miri R. Medicinal & Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shiraz, Iran aut NATIONALLICENCE 773 0- Chemistry of Heterocyclic Compounds Springer US; http://www.springer-ny.com 46/11(2011-02-01), 1354-1363 0009-3122 46:11<1354 2011 46 10593 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer