Xanthine oxidase inhibition: effect of an N-alkyl substituent on C-2 of the nucleus of 8-azahypoxanthine.
Several new 2-n-alkyl-8-azahypoxanthines were synthesized and tested. The compounds were obtained from 4(5)-amino-5(4)-carbamoyl-1,2, 3-triazole and the suitable ethyl alkanoate in the presence of sodium ethoxide. The inhibitory activity of these compounds against xanthine oxidase was dependent on the length of the alkyl chain of the substituent: 2-n-hexyl-8-azahypoxanthine was the most active product. This fact pointed out the great importance of the weak interaction between the substituent and the adjacent region of the active site of the enzyme.
Biagi
G
G
Istituto Di Chimica Farmaceutica E Tossicologica, Università Di Pisa.
Giorgi
I
I
Livi
O
O
Scartoni
V
V
Lucacchini
A
A
D055598:Chemical Phenomena; D002621:Chemistry; D007042:Hypoxanthines / Q000138:chemical synthesis* / Q000494:pharmacology; D007700:Kinetics; D014969:Xanthine Oxidase / Q000037:antagonists & inhibitors*
D007042:Hypoxanthines; C000149:8-azahypoxanthine; D014969:Xanthine Oxidase