153380-41-7

Upstream product

• 128018-17-7 Z-Pro-NH^tBu 
• 141171-72-4 (2S,3S)-3-(N-benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutyryl-L-prolyl-tert-butyl amide 
• 139069-60-6 (3S,2S)-3-amino-2-hydroxy-4-phenylbutyric acid methyl ester 
• 143978-10-3 Z-Asn-(2S,3S)-AHPBA-OH 
• 126015-23-4 (2S,3S)-3-[[(benzyloxy)carbonyl]amino]-2-hydroxy-4-phenylbutanoic acid methyl ester 
• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 143935-61-9 [(1S,2S)-1-Benzyl-3-((S)-2-tert-butylcarbamoyl-pyrrolidin-1-yl)-2-hydroxy-3-oxo-propyl]-carbamic acid tert-butyl ester 
• 153380-43-9 (S)-N-tert-butyl-1-[(2S,3S)-3-amino-2-hydroxy-4-phenylbutanoyl]pyrrolidine-2-carboxamide 
• 128018-18-8 L-proline tert-butylamide 
• 68030-64-8 (1S)-2-(tert-butylcarbamoyl)pyrrolidine-1-carboxylic acid tert-butyl ester 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 143934-31-0 (S)-N-tert-butyl-3-[(2S,3S)-3-[(S)-2-(tert-butoxycarbonyl)aminosuccinamyl]amino-2-hydroxy-4-phenylbutanoyl]pyrrolidine-2-carboxamide 
• 139694-65-8 (S)-N-tert-butyl-3-[(2S,3S)-2-hydroxy-3-[(S)-2-benzyloxycarbonylaminosuccinamyl]amino-4-phenylbutanoyl]pyrrolidine-2-carboxamide 

Downstream Products

• 207444-88-0 ((S)-1-{(S)-1-[(1S,2S)-1-Benzyl-3-((S)-2-tert-butylcarbamoyl-pyrrolidin-1-yl)-2-hydroxy-3-oxo-propylcarbamoyl]-2-carbamoyl-ethylcarbamoyl}-2-phenyl-ethyl)-carbamic acid benzyl ester 
• 207444-87-9 ((R)-1-{(S)-1-[(1S,2S)-1-Benzyl-3-((S)-2-tert-butylcarbamoyl-pyrrolidin-1-yl)-2-hydroxy-3-oxo-propylcarbamoyl]-2-carbamoyl-ethylcarbamoyl}-2-phenyl-ethyl)-carbamic acid benzyl ester 
• 141171-79-1 (S)-N-tert-butyl-3-[(2S,3S)-3-[(S)-2-(2-naphthoxyacetyl)aminosuccinamyl]amino-2-hydroxy-4-phenylbutanoyl]pyrrolidine-2-carboxamide 
• 141171-77-9 (S)-N-tert-butyl-3-[(2S,3S)-3-[(S)-2-(1-naphthoxyacetyl)aminosuccinamyl]amino-2-hydroxy-4-phenylbutanoyl]pyrrolidine-2-carboxamide 

Relevant academic research and scientific papers

Structure-activity relationship of orally potent tripeptide-based HIV protease inhibitors containing hydroxymethylcarbonyl isostere

We designed and synthesized a new class of peptidomimetic human immunodeficiency virus protease inhibitors containing a unique unnatural amino acid, allophenylnorstatine [Apns; (2S,3S)-3-amino-2-hydroxy-4-phenylbutyric acid], with a hydroxymethylcarbonyl isostere as the active moiety. From a structure-activity relationship study of HIV-1 protease inhibition, enzyme selectivity for other aspartyl proteases, the antiviral activity and pharmacokinetics in rats, 24c (KNI-227) and 24d (KNI-272, our first clinical candidate) were found to be selective and orally potent HIV protease inhibitors. Moreover, an improvement of the pharmacokinetic features of KNI-272 provided two long-lasting and highly bioavailable compounds (24g: JE-2178,h: JE-2179).

Syntheses of HIV-protease inhibitors having a peptide moiety which binds to GP120

Some HIV-protease inhibitor derivatives having an N- carbomethoxycarbonyl-prolyl-phenylalanine benzyl ester (CPF) moiety as a binding site to gp120 were designed and synthesized. Almost all the compounds bearing CPF on the phenoxyacetyl group showed protease-inhibitory activity. Compounds 25a and 25b, which have the CPF moiety at the ortho- and meta- positions of the phenoxyacetyl group, respectively, had anti-HIV activity, although the others showed only protease-inhibitory activity. These results suggest that 25b binds to gp120 and inhibits HIV protease.