Peptidyl allyl sulfones: a new class of inhibitors for clan CA cysteine proteases

Bioorganic & Medicinal Chemistry
Marion G GötzJames C Powers

Abstract

A new series of peptidyl allyl sulfone inhibitors was discovered while trying to synthesize epoxy sulfone inhibitors from vinyl sulfones using basic oxidizing conditions. The various dipeptidyl allyl sulfones were evaluated with calpain I, papain, cathepsins B and L, cruzain and rhodesain and found to be potent inhibitors. In comparison to the previously developed class of vinyl sulfone inhibitors, the novel dipeptidyl allyl sulfones were more potent inhibitors than the corresponding dipeptidyl vinyl sulfones. It was observed that the stereochemistry of the vinyl sulfone precursor played a role in the potency of the dipeptidyl allyl sulfone inhibitor.

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Citations

Aug 31, 2013·PLoS Neglected Tropical Diseases·Helton J WiggersCarlos A Montanari
Oct 26, 2011·Biochimica Et Biophysica Acta·Vito TurkDušan Turk
Jul 7, 2015·The Journal of Organic Chemistry·Antonio LatorreHerman S Overkleeft
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May 16, 2006·Bioorganic & Medicinal Chemistry Letters·Cláudia ValentePhilip J Rosenthal
Jun 22, 2006·Medicinal Research Reviews·D Christopher Meadows, Jacquelyn Gervay-Hague
Sep 1, 2005·Chromosoma·Brenda R Grimes, Zoia Larin Monaco
Apr 5, 2018·Nature Communications·Peizhong XieTeck-Peng Loh
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Dec 20, 2019·PloS One·Geraldo Rodrigues SartoriCharles A Laughton
Jan 23, 2018·The Journal of Organic Chemistry·Xue LeiYunfeng Chen
Jul 31, 2019·Journal of Medicinal Chemistry·Lorenzo CianniCarlos A Montanari

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