[Synthesis of N alpha-(benzoylglycyl)- and N alpha-(benzyloxycarbonylglycyl)-4-amidinophenylalanine amides as thrombin inhibitors].
The 4-nitrophenyl esters of hippuric acid and benzyloxycarbonylglycine had been aminolyzed by racemic 4-cyanphenylalanine into the compounds 3 and 4. After activation as 4-nitrophenyl esters and following reaction with amines the amides 7-14 were formed. These cyano compounds were converted into the amidines via the thioamides 15-22 and the thioimidic esters 23-30. The piperidide 35 was most effective against thrombin.
D000991:Antithrombins / Q000138:chemical synthesis*; D001120:Arginine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D006626:Hippurates; D013329:Structure-Activity Relationship
D000991:Antithrombins; D006626:Hippurates; C040761:N-benzyloxycarbonylarginine 4-nitrophenyl ester; D001120:Arginine; C030514:hippuric acid
Synthese von N alpha-(Benzoylglycyl)- und N alpha-(Benzyloxycarbonylglycyl)-4-amidinophenylalaninamiden als Thrombininhibitoren.