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Zusammenfassung
Enantiomeric N-aminoacyl-2,6-dimethylanilines were synthesized by condensation of optically active N,N-dimethylalanines or phenylalanines with EtO2- CCl, yielding mixed anhydrides. Reaction of these with 2,6-Me2C6H3NH2 gave optically active N-aminoacyl-2,6-dimethylanilines. Compds. synthesized were [m.p. HCl salt and [alpha ]20D (c, 0.5, H2O) given]: N-(D-N, N-dimethylalanyl)-2,6-dimethylaniline, ...
Zusammenfassung
Enantiomeric N-aminoacyl-2,6-dimethylanilines were synthesized by condensation of optically active N,N-dimethylalanines or phenylalanines with EtO2- CCl, yielding mixed anhydrides. Reaction of these with 2,6-Me2C6H3NH2 gave optically active N-aminoacyl-2,6-dimethylanilines. Compds. synthesized were [m.p. HCl salt and [alpha ]20D (c, 0.5, H2O) given]: N-(D-N, N-dimethylalanyl)-2,6-dimethylaniline, 197 Deg, -23.2 Deg; N-(L-N, N-dimethylalanyl)-2,6-dimethylaniline, 197 Deg, 23.2 Deg; N-(D-N, N-dimethylphenylalanyl)-2,6-dimethylaniline, 214 Deg, -94.7 Deg; and N-(L-N, N-dimethyl-phenylalanyl)-2,6-dimethylaniline, 211 Deg, 93.7 Deg. Concns. of these local anesthetically active compds. necessary to inhibit the conduction rate in frog heart ventricle strips by 50% were 85.0, 260.0, 58.0, and 24.0 micro moles/l., resp. These activities were apparently a function of the ability of the optically active compds. to interact with asymmetric structures of the cell membrane.
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