Inhibition of platelet aggregation by 5-nitro-2-furaldehyde diacetate with observations on structure-activity...

Nitrofurantoin [1-(5'-nitro-2'-furfurylideneamino)-2, 4-diketoimidazole] is a potent inhibitor of primary ADP-induced platelet aggregation. The nitro group on the furan ring and the specific arrangement of the two keto groups on the imidazole ring are the molecular characteristics of nitrofurantoin critical to its inhibitory effect. The present studies report that 5-nitro-2-furaldehyde diacetate is also a potent inhibitor of primary ADP-induced platelet aggregation. 5-Nitro-2-furaldehyde diproprionate, 5-nitro-2-furaldehyde dibutyrate, and 5-nitro-2-furfuryl acetate are essentially inactive. These results indicate that a diacetate moiety can replace the diketoimidazole moiety of nitrofurantoin and form a compound that fully retains the inhibitory effect upon primary ADP-induced platelet aggregation.