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- W2038018977 abstract "The structure of Ca2+ channel blockers benzofurazanyl- and benzofuroxanyl-1,4-dihydropyridines (1,4-DHPs) was investigated by an integrated NMR, X-ray diffraction and molecular graphics study. 1H- and 13C-NMR showed that all the benzofuroxan derivatives exist in solution as tautomeric mixtures. ΔG° and ΔG∗ for 4′⇄7′ and 5′⇄7′ benzofuroxanyl tautomeric equilibria were determined for the benzofuroxan derivatives VI and VII. These figures are close to those observed for other substituted benzofuroxans known from literature including DHP derivatives. The conformational domain of all the compounds was analyzed, showing two sets of energetically accessible arrangements of the heterocyclic substructure with respect to C(4)H–DHP hydrogen, antiperiplanar and synperiplanar. Rotameric preference in solution around the C(4)–C(4′) bond in benzofurazanyl derivative IV was sought by normalized transient ΔNOE spectra using interatomic distances derived from AM1 energy minimized structures. A synperiplanar fraction of ca. 75% was calculated, in keeping with results obtained by Rovnyak for Nifedipine. Finally, the solid state preferred conformation was assessed by X-ray analysis for 5′-benzofurazanyl (V) and 5′(6′)-benzofuroxanyl (VII) derivatives. The latter in the solid state prefers the 5′-form (VIIa). The pentatomic ring systems always lie on the same side of the C(4)H–DHP hydrogen. This was also found to be the case for 4′-substituted derivatives and a large number of dihydropyridine derivatives." @default.
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- W2038018977 date "2000-05-01" @default.
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- W2038018977 title "Structural investigation of Ca 2+ antagonists benzofurazanyl and benzofuroxanyl-1,4-dihydropyridines" @default.
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- W2038018977 doi "https://doi.org/10.1016/s0022-2860(99)00386-5" @default.
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