4 research outputs found

    Dipeptidyl α-fluorovinyl Michael acceptors: Synthesis and activity against cysteine protease

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    The synthesis of novel dipeptidyl α-fluorovinyl sulfones using a Horner–Wadsworth–Emmons approach on N-Boc-l-phenylalaninal is described. Inhibitory assays against a Leishmania mexicana cysteine protease (CPB2.8ΔCTE) revealed low biological activity. Relative rates of Michael additions of 2′-(phenethyl)thiol with vinyl sulfone and α-fluorovinyl sulfone were determined, and ab initio calculations on several Michael acceptor model structures were performed; both were in agreement with the biological testing
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