Organic nitrates. O-(2,3-dihydroxypropyl)-1,4:3,6-dianhydro-hexitol-nitrates

Several hybrid molecules have been synthesized which contain both the 1,4:3,6-dianhydro-hexitol (isohexide) and glycerol partial structures, with nitrate ester groups at different positions. Alkylation of the isohexide ring system with suitable 3-carbon units generates compounds with the 2,3-epoxypropyl side chain as key intermediates. Ring opening of these oxiranes under various conditions yield primary and secondary nitrates as well as dinitrates. Pharmacological screening shows that the new structures are much less active than the parent compounds.