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

Authors

  • A. Shahrisa Department of Organic and Biochemistry, Faculty of Chemistry, University of Tabriz, Tabriz
  • M. Zirak Department of Organic and Biochemistry, Faculty of Chemistry, University of Tabriz, Tabriz
  • A. R. Mehdipour Medicinal & Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shiraz
  • R. Miri Medicinal & Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shiraz

DOI:

https://doi.org/10.1007/6149

Keywords:

calcium channel antagonist, dihydropyridines, 2-pyrone derivatives, Hantzsch reaction

Abstract

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 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 excess amount of NH4OAc. Also 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 were assessed in which they demonstrated moderate to weak effects, although, one compound had a comparable effect (IC50 =1.40×10-7 M) regarding to reference drug, Nifedipine.

How to Cite
Shahrisa, A.; Zirak, M.; Mehdipour, A. R.; Miri, R. Chem. Heterocycl. Compd. 2011, 46, 1354. [Khim. Geterotsikl. Soedin. 2010, 1670.]

For this article in the English edition see
DOI 10.1007/s10593-011-0672-9

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Published

2021-02-10

Issue

No. 11 (2010)

Section

Original Papers