Schönenberger, Helmut and Petter, Alfred and Zwez, W. (1968) Enantiomeric local anesthetics of the N-aminoacyl-2,6-dimethylaniline type. Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft 301 (10), pp. 780-785.
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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.
|Additional information (public):||CAN 70:38061 34 Synthesis of Amino Acids, Peptides, and Proteins 17655-31-1 (Amide) Role: BAC (Biological activity or effector, except adverse), BIOL (Biological study) (aminoacyl 2,6-xylidides, as anesthetics); 19216-71-8; 19216-72-9; 19216-73-0; 19237-86-6 Role: BAC (Biological activity or effector, except adverse), BSU (Biological study, unclassified), THU (Therapeutic use), BIOL (Biological study), USES (Uses) (anesthetic activity of); 21400-92-0P; 21400-93-1P; 21400-94-2P; 21400-95-3P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of)|
|Institutions:||Chemistry and Pharmacy > Institute of Pharmacy > Retired Professors > Prof. Schönenberger|
|Keywords:||Anesthetics (aminoacyl 2,6-xylidides) aminoacyl aniline anesthetic aniline aminoacyl anesthetic anesthetic aminoacyl aniline|
|Subjects:||500 Science > 540 Chemistry & allied sciences|
|Refereed:||Yes, this version has been refereed|
|Created at the University of Regensburg:||Unknown|
|Deposited On:||19 Nov 2010 08:55|
|Last Modified:||19 Nov 2010 08:55|