Synthesis of monomeric and dimeric steroids containing [1,2,4]triazolo[1,5-a]pyrimidines

Abstract

The synthesis of several monomeric and dimeric steroidal [1,2,4]triazolo[1,5-a]pyrimidines (TPs) derived from steroids are described. These derivatives were prepared from α,β-unsaturated carbonyl compounds through a Claisen Schmidt condensation and rearrangement of the spiro moiety followed by a cycloaddition with 3-amino-1,2,4-triazole. The antiproliferative activity of compounds 7, 13-15 was tested against human cancer cells; several IG₅₀ values were below 10μM.

Keywords: Cycloaddition; Heterocyclic compounds; Steroids; [1,2,4]Triazolo[1,5-a]pyrimidine; α,β-Unsaturated ketones.