862175-07-3

Upstream product

• 109183-71-3 N-(tert-butoxycarbonyl)-L-cyclohexylglycine 
• 107202-38-0 tert-butyl (S)-(methoxycarbonyl)(cyclohexyl)methylcarbamate 
• 145618-11-7 (S)-amino(cyclohexyl)acetic acid methyl ester 
• 1149-26-4 (S)-N-(benzyloxycarbonyl)valine 
• 862118-93-2 (S)-((S)-2-benzyloxycarbonylamino-3-methylbutyrylamino)cyclohexylacetic acid methyl ester 
• 862175-13-1 (S)-((S)-2-amino-3-methylbutyrylamino)cyclohexylacetic acid methyl ester 

Relevant academic research and scientific papers

Synthesis of novel potent hepatitis C virus NS3 protease inhibitors: Discovery of 4-hydroxy-cyclopent-2-ene-1,2-dicarboxylic acid as a N-acyl-l-hydroxyproline bioisostere

Potent tetrapeptidic inhibitors of the HCV NS3 protease have been developed incorporating 4-hydroxy-cyclopent-2-ene-1,2-dicarboxylic acid as a new N-acyl-l-hydroxyproline mimic. The hydroxycyclopentene template was synthesized in eight steps from commercially available (syn)-tetrahydrophthalic anhydride. Three different amino acids were explored in the P1-position and in the P2-position the hydroxyl group of the cyclopentene template was substituted with 7-methoxy-2-phenyl-quinolin-4-ol. The P3/P4-positions were then optimized from a set of six amino acid derivatives. All inhibitors were evaluated in an in vitro assay using the full-length NS3 protease. Several potent inhibitors were identified, the most promising exhibiting a Ki value of 1.1 nM.

HCV NS-3 SERINE PROTEASE INHIBITORS

Peptidomimetic compounds are described which inhibit the NS3 protease of the hepatitis C virus (HCV). The compounds have the formula where the variable definitions are as provided in the specification. The compounds comprise a carbocyclic P2 unit in conjunction with a novel linkage to those portions of the inhibitor more distal to the nominal cleavage site of the native substrate, which linkage reverses the orientation of peptidic bonds on the distal side relative to those proximal to the cleavage site.