Synthesis of alpha-trinositol related analogues. Structure-activity (analgesic and anti-inflammatory) relationships

alpha-Trinositol analogues, including methyl ethers, deoxy, oxa and aza derivatives were prepared. The parent compound possesses weak analgesic and anti-inflammatory properties. Removal of the non-phosphorylated hydroxyls generates a compound devoid of analgesic activity but which retains the anti-inflammatory property of the parent compound. The protection of these hydroxyls as methyl ethers leads to compounds which keep their anti-inflammatory activity, whereas the replacement of the cyclohexane carbone backbone by a tetrahydropyrane or a piperidine ring leads to compounds which increase the pain.