Crystal structures of calcium channel antagonists: 2,6-dimethyl-3,5-dicarbomethoxy-4-[2-nitro-, 3-cyano-, 4-(dimethylamino)-, and 2,3,4,5,6-pentafluorophenyl]-1,4-dihydropyridine

The crystal structures of 2,6-dimethyl-3,5-dicarbomethoxy-4-(2-nitrophenyl)-1,4-dihydropyridine (Nifedipine) and the 3-cyano-, 4-(dimethylamino)- and 2,3,4,5,6-pentafluorophenyl derivatives were determined. The 1,4-dihydropyridine ring in all four compounds has a boat-type conformation with varying...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1980-12, Vol.23 (12), p.1442-1445
Main Authors: Triggle, A. M, Shefter, E, Triggle, D. J
Format: Article
Language:English
Subjects:
Animals
Calcium - metabolism
Guinea Pigs
In Vitro Techniques
Ion Channels - drug effects
Models, Molecular
Molecular Conformation
Muscle Contraction - drug effects
Muscle, Smooth - drug effects
Nifedipine - analogs & derivatives
Pyridines
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Summary:The crystal structures of 2,6-dimethyl-3,5-dicarbomethoxy-4-(2-nitrophenyl)-1,4-dihydropyridine (Nifedipine) and the 3-cyano-, 4-(dimethylamino)- and 2,3,4,5,6-pentafluorophenyl derivatives were determined. The 1,4-dihydropyridine ring in all four compounds has a boat-type conformation with varying degrees of puckering at the C4 position. Increasing distortion from planarity at this position shows a limited correlation with decreasing biological activity, determined as the ability to inhibit the Ca2+-dependent muscarinic-induced mechanical responses of guinea pig ileal longitudinal smooth muscle.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00186a029