Bioorganic and Medicinal Chemistry Letters p. 2173 - 2176 (1996)
Update date:2022-08-29
Topics:
Palmer, Robert B.
Andersen, Niels H.
We report the synthesis and X-ray crystal structure of 1,4-dihydro-2,6-dimethyl-4-(2'-isopropylphenyl)-3,5-pyridine-dicarboxy lic acid dimethyl ester (4), an analogue of the 1,4-dihydropyridine calcium channel antagonist, nifedipine. Solution state NOE data indicate the presence of both rotameric forms. The solid state shows exclusively one rotamer of 4 (that in which the 2'-isopropyl substituents is syn with C4H, which is also the major solution state rotamer). The 3,5-methyl esters adopt an ap/sp orientation with respect to the dihydropyridine double bonds in the solid state.
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