863640-20-4

Upstream product

• 2577-48-2 methyl (2S)-pyrrolidine carboxylate 
• 62023-59-0 (2S,3S)-3-benzyloxycarbonylamino-2-hydroxy-4-phenylbutanoic acid 
• 2133-40-6 L-proline methyl ester monohydrochloride 
• 172696-23-0 (2S,3S)-N-(benzyloxycarbonyl)-AHAP-(3-amino-2-hydroxy-4-phenylbutanoic acid) ethyl ester 
• 121253-57-4 β-<<(phenylmethoxy)carbonyl>amino>-α-oxobenzenebutanoic acid ethyl ester 
• 121253-53-0 2-ethoxy-5-phenyl-4-<<(phenylmethoxy)carbonyl>amino>-3-oxo-1-pentene 
• 114744-85-3 [(S)-1-(methoxy-methyl-carbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester 

Relevant academic research and scientific papers

Novel 3-amino-2-hydroxy acids containing protease inhibitors. Part 1: Synthesis and kinetic characterization as aminopeptidase P inhibitors

Novel, potent inhibitors of aminopeptidase P, containing a 3-amino-2-hydroxy acid and a proline or a proline analogues, have been prepared. One part of the bestatin-derived inhibitors was found to inhibit APP from Escherichia coli and from rat intestine a

Selectivity in the inhibition of HIV and FIV protease: Inhibitory and mechanistic studies of pyrrolidine-containing α-keto amide and hydroxyethylamine core structures

This paper describes the development of new pyrrolidine-containing α-keto amide and hydroxyethylamine core structures as mechanism based inhibitors of the HIV and FIV proteases. It was found that the α-keto amide core structure 2 is approximately 300-fold better than the corresponding hydroxyethylamine isosteric structure and 1300-fold better than the corresponding phosphinic acid derivative as an inhibitor of the HIV protease. The α-keto amide is however not hydrated until it is bound to the HIV protease as indicated by the NMR study and the X-ray structural analysis. Further analysis of the inhibition activities of hydroxyethylamine isosteres containing modified pyrrolidine derivatives revealed that a cis-methoxy group at C-4 of the pyrrolidine would improve the binding 5- and 25-fold for the trans-isomer. When this strategy was applied to the α-keto amide isostere, a cis-benzyl ether at C-4 was found to enhance binding 3-fold. Of the core structures prepared as inhibitors of the HIV protease, none show significant inhibitory activity against the mechanistically identical FIV protease, and additional complementary groups are needed to improve inhibition.