Chemoselective Synthesis and Anti-Kinetoplastidal Properties of 2,6-Diaryl-4<em>H</em>-tetrahydro-thiopyran-4-one <em>S</em>-Oxides: Their Interplay in a Cascade of Redox Reactions from Diarylideneacetones

2,6-Diaryl-4H-tetrahydro-thiopyran-4-ones and corresponding sulfoxide and sulfone derivatives were designed to lower the major toxicity of their parent anti-kinetoplatidal diarylideneacetones through a prodrug effect. Novel diastereoselective methodologies were developed and generalized from diarylideneacetones and 2,6-diaryl-4H-tetrahydro-thiopyran-4-ones to allow the introduction of a wide substitution profile and to prepare the related S-oxides. The in vitro biological activity …