Simple antitumor model compounds for cross-conjugated cyclopentenone prostaglandins

Unstable methyl (5-methylidene-4-oxocyclopent-2-en-1-yl)acetate, having a ring moiety of J-type prostaglandins (PGJs) and similar cytotoxicity, reacts with EtSH and other thiols with formation of mono-and bis-adducts, which have been further converted by oxidation with mCPBA into corresponding stable mono-sulfones possessing cytotoxic effect most probably due to in vivo regeneration of the starting dienone. Thus, the derived sulfones can be used as transport forms for original dienone as a pharmacologically important moiety of Δ¹²-PGJ₂ and similar prostaglandins.