Abstract
□Asymmetric 2,6-dimethyl-4-aryl-1,4-dihydropyridine-3,5-dicarboxylate with [N-(3,4-methylenedioxybenzyl)-N-methyl] aminoethyl group as the ester moiety and related 1,4-dihydropyridine derivatives were prepared and tested for the effects on vascular smooth muscles. 2,6-dimethyl-4-(3′-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-[N-(3′, 4′-methylenedioxybenzyl)-N-methyl] aminoethyl ester 5-methyl ester (11) and 2,6-dimethyl-4-(3′-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-[N-2′,3′-methylenedioxybenzyl)-N-methyl] aminoethyl ester 5-ethyl ester (15) showed potent vasodilating activities. IC50 (10−8 M) was 2.6 and 2.7 for11 and15, compared with 3.5 for nicardipine.
Similar content being viewed by others
Literature Cited
Grün Von G. and Fleckenstein, A.: Die elektromechanische Entkoppelung der glatten Gefa β muskulatur als Grundprinzip der Coronardilatation durch 4-(2′-Nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarbonsäure dimethylester (BAY a 1040, Nifedipine).Arzneim.—Forsch. (Drug Res.),22, 334 (1972).
Bossert, F. and Vater, W.: Dihydropyridine, eine neu Gruppe stark wisksamer Coronartherapeutika.Naturwissenschaften,58, 578 (1979).
Meyer Von H., Bossert F., Wehinger, E., Stoepel, K. and Vater W.: Synthese und Vergleichende Pharmakologische Untersuchungen von 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl) pyridine-3, 5-dicarbonsäureestern mit nicht-identischen Ester-funktionen.Arzeneim.—Foresch. (Drug Res.),31, 407 (1981).
Bossert F., Meyer H. and Wehinger, E.: 4-Aryldihydropyridines, a New Class of Highly Active Calcium Antagonists.Angew. Chem. Int. Ed. Eng.,20, 762 (1981).
Prous, J., Blancafort, P., Castaner, J., Serradell, M.N. and Mealy N.: Biologically Active 1,4-Dihydropyridine Derivatives.Drugs of the Future,6, 427 (1981).
Janis, R.A. and Triggle, D.J.: New Developments in Ca2+ Channel Antagonists.J. Med. Chem. 26, 775 (1983).
Iwanami, M., Shibanuma, T., Fujimoto, M., Kawai, R., Tamazawa, K., Takenaka, T., Takahashi, K. and Murakami, M.: Synthesis of New Water-Soluble Dihydropyridine Vasodilators.Chem. Pharm. Bull. 27, 1426 (1979).
Ohno, S., Komatsu, O., Mizukoshi, K., Ichihara, K.: Synthesis of Asymmetric 4-Aryl-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylates with Vasodilating and Antihypertensive Activities.Chem. Pharm. Bull. 34, 1589 (1986).
Suh, J.J. and Hong, Y.H.: Synthesis of 1,4-Dihydropyridine Carboxylic Acids.Yakhak Hoeji,33, 80 (1989).
Suh, J.J. and Hong, Y.H.: Synthesis of 1,4-Dihydropyridine Carboxylic Acids (II).Yakhak Hoeji,33, 219 (1989).
Muto, K., Kuroda, T., Karasawa, A., Yamada, K. and Nakamizo, N.: 1,4-Dihydropyridine derivatives.European patent Application,106, 275 (1983).
Hof, R.P. and Vuorela, H.J.: Assessing Calcium Antagonism on Vascular Smooth Muscle: A Comparison of Three Methods.J. Pharmacol. Methods,9, 41 (1983).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Suh, J., Lee, B., Kim, C. et al. Synthesis of 1,4-dihydropyridine derivatives with vasodilating activities (I). Arch. Pharm. Res. 13, 240–245 (1990). https://doi.org/10.1007/BF02856528
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02856528