799560-52-4

Upstream product

• 98978-44-0 (E)-3-(1-naphthyl)prop-2-en-1-ol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1253912-53-6 C₁₈H₂₁NO₃ 
• 108-98-5 thiophenol 

Downstream Products

• 1253912-11-6 N-((S)-1-((R,E)-1-(naphthalen-1-yl)-3-(phenylsulfonyl)allylamino)-1-oxo-3-phenylpropan-2-yl)morpholine-4-carboxamide 
• 1253912-22-9 N-((S)-4-methyl-1-((R,E)-1-(naphthalen-1-yl)-3-(phenylsulfonyl)allylamino)-1-oxopentan-2-yl)morpholine-4-carboxamide 
• 1253912-33-2 4-methyl-N-((S)-1-((R,E)-1-(naphthalen-1-yl)-3-(phenylsulfonyl)allylamino)-1-oxo-3-phenylpropan-2-yl)piperazine-1-carboxamide 
• 1253912-43-4 4-methyl-N-((S)-4-methyl-1-((R,E)-1-(naphthalen-1-yl)-3-(phenylsulfonyl)allylamino)-1-oxopentan-2-yl)piperazine-1-carboxamide 
• 1253911-98-6 (3R,E)-3-(tert-butoxycarbonylamino)-3-(1-naphthyl)-1-phenylsulfonyl-1-propene 
• 1253911-99-7 (3R,E)-3-amino-3-(1-naphthyl)-1-phenylsulfonyl-1-propene trifluoroacetate salt 
• 799560-38-6 C₂₄H₂₇NO₅S 

Relevant academic research and scientific papers

Novel peptidyl aryl vinyl sulfones as highly potent and selective inhibitors of cathepsins L and B

Herein we present the design, synthesis, and evaluation of a structurally novel library of 20 peptidyl 3-aryl vinyl sulfones as inhibitors of cathepsins L and B. The building blocks, described here for the first time, were synthesized in a highly efficient and enantioselective manner, starting from 3-aryl-substituted allyl alcohols. The corresponding vinyl sulfones were prepared by a new approach, based on a combination of solid-phase peptide synthesis using the Fmoc/tBu strategy, followed by solution-phase coupling to the corresponding (R)-3-amino-3-aryl vinyl sulfones as trifluoroacetate salts. The inhibitory activity of the resulting compounds against cathepsins L and B was evaluated, and the compound exhibiting the best activity was selected for enzymatic characterization. Finally, docking studies were performed in order to identify key structural features of the aryl substituent.