1359969-54-2

Upstream product

• 21691-53-2 L-leucine tert-butyl ester 
• 1447047-18-8 C₃₃H₄₄N₆O₈ 
• 1447047-16-6 methyl (S)-6-(4-((4-((S)-2-(((benzyloxy)carbonyl)amino)-3-(((S)-1-(tert-butoxy)-4-methyl-1-oxopentan-2-yl)amino)-3-oxopropyl)phenoxy)methyl)-1H-1,2,3-triazol-1-yl)-2-((tert-butoxycarbonyl)amino)hexanoate 
• 1447047-13-3 tert-butyl (S)-2-((S)-2-(((benzyloxy)carbonyl)amino)-3-(4-(prop-2-yn-1-yloxy)phenyl)propanamido)-4-methylpentanoate 
• 846549-33-5 dicyclohexylammonium N-tert-butyloxycarbonyl-2-amino-6-azidohexanoate 
• 13734-28-6 Boc-Lys-OH 
• 7517-19-3 methyl (L)-leucinate hydrochloride 
• 1359969-48-4 methyl (12S,15S,18S)-18-{[(benzyloxy)carbonyl]amino}-15-(2-methylpropyl)-14,17-dioxo-2-oxa-5,6,7,13,16-pentaazatricyclo[18.2.2.1(4,7)]pentacosa-1⁽²²⁾,4⁽²⁵⁾,5,20,23-pentaene-12-carboxylate 
• 1359969-42-8 (5S,8S,11S)-methyl 11-(4-azidobutyl)-8-isobutyl-3,6,9-trioxo-1-phenyl-5-(4-(prop-2-yn-1-yloxy)benzyl)-2-oxa-4,7,10-triazadodecan-12-oate 
• 1359969-36-0 (S)-2-((S)-2-(((benzyloxy)carbonyl)amino)-3-(4-(prop-2-yn-1-yloxy)phenyl)propanamido)-4-methylpentanoic acid 
• 1359969-32-6 (S)-methyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-(4-(prop-2-yn-1-yloxy)phenyl)propanamido)-4-methylpentanoate 
• 1359970-01-6 (S)-methyl 2-amino-6-azidohexanoate hydrochloride 
• 1359969-23-5 (S)-2-(((benzyloxy)carbonyl)amino)-3-(4-(prop-2-yn-1-yloxy)phenyl)propanoic acid 

Downstream Products

• 1359968-98-1 benzyl N-[(12S,15S,18S)-12-formyl-15-(2-methylpropyl)-14,17-dioxo-2-oxa-5,6,7,13,16-pentaazatricyclo[18.2.2.1(4,7)]pentacosa-1⁽²²⁾,4⁽²⁵⁾,5,20,23-pentaen-18-yl]carbamate 

Relevant academic research and scientific papers

Synthesis and extended activity of triazole-containing macrocyclic protease inhibitors

Peptide-derived protease inhibitors are an important class of compounds with the potential to treat a wide range of diseases. Herein, we describe the synthesis of a series of triazole- containing macrocyclic protease inhibitors pre-organized into a b-strand conformation and an evaluation of their activity against a panel of proteases. Acyclic azidoalkyne-based aldehydes are also evaluated for comparison. The macrocyclic peptidomimetics showed considerable activity towards calpain II, cathepsin L and S, and the 20S proteasome chymotrypsin-like activity. Some of the first examples of highly potent macrocyclic inhibitors of cathepsin S were identified. These adopt a well-defined b-strand geometry as shown by NMR spectroscopy, X-ray analysis, and molecular docking studies.

New β-strand templates constrained by Huisgen cycloaddition

New peptidic templates constrained into a β-strand geometry by linking acetylene and azide containing P1 and P3 residues of a tripeptide by Huisgen cycloaddition are presented. The conformations of the macrocycles are defined by NMR studies and those that best define a β-strand are shown to be potent inhibitors of the protease calpain. The β-strand templates presented and defined here are prepared under optimized conditions that should be suitable for targeting a range of proteases and other applications requiring such a geometry.