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Unusual nitration of substituted 7‐amino‐1,8‐naphthyridine in the synthesis of compounds with antiplatelet activity

1997; Wiley; Volume: 34; Issue: 5 Linguagem: Inglês

10.1002/jhet.5570340520

1943-5193

Pier Luigi Ferrarini, Claudio Mori, Muwaffag Badawneh, Clementina Manera, Adriano Martinelli, Federico Romagnoli, Giuseppe Saccomanni, Mauro Miceli,

Organic Chemistry Cycloaddition Reactions

Abstract Several 1,8‐naphthyridine derivatives have been diazotizated to obtain the corresponding hydroxy derivatives or mixture of hydroxy and hydroxy nitro derivatives. The respective amounts of hydroxy and hydroxy nitro derivatives depends on the nature of the substituents, on their position on the naphthyridine nucleus, on the amount of sodium nitrite and on the reaction temperature. A study of the electronic density of some molecules suggests a possible explanation of the effects induced by the nature of the substituents and of their position. Some of the compounds were tested for their ability to inhibit human platelet aggregation in vitro induced by arachidonic acid. Only compound 26 showed interesting antiplatelet activity.