866553-49-3Relevant academic research and scientific papers
Synthesis of α-trifluoromethyl-α-amino-β-sulfone hydroxamates: Novel nanomolar inhibitors of matrix metalloproteinases
Sinisi, Roberta,Sani, Monica,Candiani, Gabriele,Parente, Rachele,Pecker, Fran?oise,Bellosta, Stefano,Zanda, Matteo
, p. 6515 - 6518 (2007/10/03)
The racemic α-trifluoromethyl-α-amino-β-sulfone hydroxamates 1 were synthesized by means of a nucleophilic addition of sulfur-stabilized carbanions to a N-Cbz imine of trifluoropyruvate (4). The free amino derivative 1a was the most potent inhibitor of both MMP-3 (stromelysin-1) and MMP-9 (gelatinase-B), showing an IC50 = 14 nM and 1 nM, respectively, and excellent selectivity versus MMP-1 (>5000-fold difference in inhibitory capacity). The N-Me derivative 1b was the most selective for MMP-3 with respect to MMP-9 (62-fold difference).
