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1. Calcium channel blocking and positive inotropic activities of ethyl 5-cyano-1,4-dihydro-6-methyl-2-[(phenylsulfonyl)methyl]-4-aryl-3-pyridinecarboxylate and analogs. Synthesis and structure-activity relationships

Author

Ila Sircar, Thomas A. Pugsley, Yu Hsin Shih, Michael Taylor, Eva K. Gregor, Stehen J. Haleen, Kevin R. Anderson, R. P. Steffen, and Ronald E. Weishaar

Subjects
Dihydropyridines, Chemical Phenomena, Nitrile, Stereochemistry, Guinea Pigs, Carboxylic Acids, Muscle, Smooth, Vascular, Sulfone, Structure-Activity Relationship, chemistry.chemical_compound, Nitriles, Drug Discovery, Animals, Structure–activity relationship, Sulfones, Aryl, Calcium channel, Nicotinic Acids, Sulfoxide, Biological activity, Calcium Channel Blockers, Myocardial Contraction, Rats, Chemistry, chemistry, Molecular Medicine, Rabbits, Enantiomer
Abstract

The synthesis and pharmacological evaluation of a series of 2-[(arylsulfonyl)methyl]-4-aryl-5-cyano-1,4-dihydropyridine-3-carboxylic acid esters and analogues are described. These compounds possess a unique profile namely, calcium channel blocking and positive inotropic activities in vitro. Compound 54 was selected as the best compound in the series and was studied in detail. The synthesis and biological profiles of enantiomers of 54 are also reported. The data indicate that although the calcium channel blocking property of 54 is stereospecific the positive inotropic activity is not. Examples of 3- and 6-cyano and other closely related 1,4-dihydropyridine derivatives are described and evaluated for comparison and were found to be devoid of dual activities mentioned above.

Published
1991
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