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Synthesis and evaluation of stereopure α-trifluoromethyl-malic hydroxamates as inhibitors of matrix metalloproteinases |
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| Authors: | Monica Sani Dorina Belotti Walter Panzeri Matteo Zanda |
| Institution: | a Dipartimento di Chimica, Materiali ed Ingegneria Chimica “G.Natta” del Politecnico di Milano, via Mancinelli 7, I-20131 Milan, Italy b CNR--Istituto di Chimica del Riconoscimento Molecolare, sezione “A. Quilico”, via Mancinelli 7, I-20131 Milan, Italy c Istituto di Ricerche Farmacologiche Mario Negri, Laboratori Negri, via Gavazzeni 11, I-24125 Bergamo, Italy |
| Abstract: | The total synthesis of trifluoromethyl (Tfm) analogs of known nanomolar matrix metalloproteinases (MMPs) inhibitors has been performed. The synthetic protocol is based on a moderately stereoselective aldol reaction of trifluoropyruvate with an N-acyl-oxazolidin-2-thione for the construction of the core α-Tfm-malic unit. Both the diastereomeric forms of the target α-Tfm-malic hydroxamates showed micromolar inhibitory potency toward MMP-2 and 9, with a substantial drop with respect to the parent unfluorinated compounds. |
| Keywords: | Fluorine Peptidomimetics Matrix metalloproteinases |
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