Pl. Ferrarini et al., UNUSUAL NITRATION OF SUBSTITUTED 7-AMINO-1,8-NAPHTHYRIDINE IN THE SYNTHESIS OF COMPOUNDS WITH ANTIPLATELET ACTIVITY, Journal of heterocyclic chemistry, 34(5), 1997, pp. 1501-1510
Several 1,8-naphthyridine derivatives have been diazotizated to obtain
the corresponding hydroxy derivatives or mixture of hydroxy and hydro
xy nitro derivatives. The respective amounts of hydroxy and hydroxy ni
tro derivatives depends on the nature of the substituents, on their po
sition on the naphthyridine nucleus, on the amount of sodium nitrite a
nd on the reaction temperature. A study of the electronic density of s
ome molecules suggests a possible explanation of the effects induced b
y the nature of the substituents and of their position. Some of the co
mpounds were tested for their ability to inhibit human platelet aggreg
ation in vitro induced by arachidonic acid. Only compound 26 showed in
teresting antiplatelet activity.