[Synthesis of N alpha-(tosyl-beta-alanyl)- and N alpha-(tosyl-epsilon-aminocapronyl)amidinophenylalanineamides as strongly effective inhibitors of thrombin].
The headline compounds were prepared for further determination of structure-activity-relationships. By conversion of cyanophenylalanines with the acidic chloride of tosyl-beta-alanine resp. tosyl-epsilon-aminocapronic acid and aminolysis of the following prepared p-nitrophenylic esters the cyano compounds would get the desired structure, which were converted over the thioamides and thioimidic esters in the amidines by the common way. At the preparation of epsilon-aminocapronic acid derivatives occurred difficulties because of simultaneous formation of the N-tosyl-epsilon-caprolactame. The preparation of corresponding aminobutyric acid derivatives wasn't possible. The prolongation of the C-chain of the branchless amino acid decreased the antithrombine effect.
D000614:Aminocaproates / Q000138:chemical synthesis* / Q000494:pharmacology; D055598:Chemical Phenomena; D002621:Chemistry; D013329:Structure-Activity Relationship; D013917:Thrombin / Q000037:antagonists & inhibitors*
D000614:Aminocaproates; D013917:Thrombin
Synthese von N alpha-(Tosyl-beta-alanyl)- und N alpha-(Tosyl-epsilon-aminocapronyl)amidinophenylalaninamiden als stark wirksame Thrombininhibitoren.