1333426-91-7

Upstream product

• 623169-05-1 (E)-(S)-2-methyl-propane-2-sulfinic acid 1-cyclohexyl-methylideneamide 
• 1066-54-2 trimethylsilylacetylene 
• 2043-61-0 cyclohexanecarbaldehyde 

Downstream Products

• 1333428-08-2 C₁₈H₂₇N₅O₂ 
• 1333428-27-5 C₁₈H₂₈N₆O₃ 
• 1333427-85-2 C₁₇H₂₈N₆O₃ 
• 1333426-93-9 (S)-N-((S)-1-cyclohexylprop-2-yn-1-yl)-tert-butylsulfinamide 
• 1333427-54-5 C₁₄H₂₂N₂O₂ 
• 1333425-63-0 morpholine-4-carboxylic acid {(S)-[1-((R)-cyano-methyl-methyl)-1H-[1,2,3]triazol-4-yl]-cyclohexyl-methyl}-amide 
• 1333428-03-7 C₁₇H₂₉N₅O₂S 
• 1333428-07-1 C₁₈H₂₉N₅O₃ 
• 1333428-20-8 C₂₀H₃₃N₅O 
• 1333428-41-3 C₁₇H₂₂ClN₇O 
• 1333428-42-4 C₂₅H₃₂N₈O 
• 1333425-33-4 morpholine-4-carboxylic acid {(S)-[1-(1-cyano-cyclopropyl)-1H-[1,2,3]triazol-4-yl]-cyclohexyl-methyl}-amide 
• 1333426-28-0 oxazole-5-carboxylic acid {(S)-[1-(1-cyano-cyclopropyl)-1H-[1,2,3]triazol-4-yl]-cyclohexyl-methyl}-amide 
• 1333426-25-7 furan-3-carboxylic acid {(S)-[1-(1-cyano-cyclopropyl)-1H-[1,2,3]triazol-4-yl]-cyclohexyl-methyl}-amide 

Relevant academic research and scientific papers

Asymmetric synthesis of propargylamines as amino acid surrogates in peptidomimetics

The amide moiety of peptides can be replaced for example by a triazole moiety, which is considered to be bioisosteric. Therefore, the carbonyl moiety of an amino acid has to be replaced by an alkyne in order to provide a precursor of such peptidomimetics. As most amino acids have a chiral center at Cα, such amide bond surrogates need a chiral moiety. Here the asymmetric synthesis of a set of 24 N-sulfinyl propargylamines is presented. The condensation of various aldehydes with Ellman's chiral sulfinamide provides chiral N-sulfinylimines, which were reacted with (trimethylsilyl)ethynyllithium to afford diastereomerically pure N-sulfinyl propargylamines. Diverse functional groups present in the propargylic position resemble the side chain present at the Cα of amino acids. Whereas propargylamines with (cyclo)alkyl substituents can be prepared in a direct manner, residues with polar functional groups require suitable protective groups. The presence of particular functional groups in the side chain in some cases leads to remarkable side reactions of the alkyne moiety. Thus, electron-withdrawing substituents in the Cα-position facilitate a base induced rearrangement to α,β-unsaturated imines, while azide-substituted propargylamines form triazoles under surprisingly mild conditions. A panel of propargylamines bearing fluoro or chloro substituents, polar functional groups, or basic and acidic functional groups is accessible for the use as precursors of peptidomimetics.

Exploration of cathepsin S inhibitors characterized by a triazole P1-P2 amide replacement

This paper details exploration of a class of triazole-based cathepsin S inhibitors originally reported by Ellman and co-workers. SAR studies involving modifications across the whole inhibitor provide a perspective on the strengths and weaknesses of this class of inhibitors. In addition, we put the unique characteristics of this class of compounds into perspective with other classes of cathepsin S inhibitors.

HETEROARYL NITRILE COMPOUNDS USEFUL AS INHIBITORS OF CATHEPSIN-S

Disclosed are Cathepsin-S reversible inhibitor compounds of the formula (I) which are useful in the treatment of autoimmune and other diseases. Also disclosed are pharmaceutical compositions containing the same, and methods of making and using the same.