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

•Synthesis of novel monomeric and dimeric steroidal triazolopyrimidines derivatives.•The stereochemistry of α,β-unsaturated ketone was established by X-ray analysis.•Values of the antiproliferative activity of some compounds are below 10 μm.

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 10 μM.

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