The search for new antiarrhythmics in the group of chirally 1,2-aminoalcohols. I. 3',4',5'-trimethoxybenzoic acid esters of optically active N,N'-dimethyl-N,N'-bis-(1-hydroxybutyl-2) ethylenediamines.
Both enantiomeric (2S, 2'S) and (2'R) N, N'-dimethyl-N, N-bis (1-hydroxybutyl-2)-ethylenediamines (Table 1) were obtained by methylation of the corresponding N,N'-ethylene-bis-2-aminobutanols-1. The esterification of the former aminoalcohols with 3, 4, 5-trimethoxybenzoic acid gave the both enantiomeric in title named esters (Table 2). The isomer with S configuration at both chirally center (C2 and C2), has a particularly strong antiarrhythmic properties (about 10-20 greater than quinidine or procaine amide in different experimental arrhythmia models in animals. The 2R,2'R enantiomere is 10-100 times less active one. It seems that the antiarrhythmic activity of this new group of antiarrhythmically active compounds, derivatives of chirally 1, 2-aminoalcohols is connected with spatial configuration.
D000605:Amino Alcohols / Q000138:chemical synthesis / Q000494:pharmacology; D000889:Anti-Arrhythmia Agents / Q000138:chemical synthesis*; D005029:Ethylenediamines / Q000138:chemical synthesis* / Q000494:pharmacology; D005707:Gallic Acid / Q000031:analogs & derivatives / Q000138:chemical synthesis
D000605:Amino Alcohols; D000889:Anti-Arrhythmia Agents; D005029:Ethylenediamines; C030706:butobendin; D005707:Gallic Acid