141171-72-4

Basic information

• Product Name: (2S,3S)-3-(N-benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutyryl-L-prolyl-tert-butyl amide
• Synonyms: (2S,3S)-3-(N-benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutyryl-L-prolyl-tert-butyl amide
• CAS NO: 141171-72-4
• Molecular Weight: 481.592
• Mol File: 141171-72-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (2S,3S)-3-(N-benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutyryl-L-prolyl-tert-butyl amide(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S)-3-(N-benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutyryl-L-prolyl-tert-butyl amide(141171-72-4)
• EPA Substance Registry System: (2S,3S)-3-(N-benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutyryl-L-prolyl-tert-butyl amide(141171-72-4)

Safety Data

• Hazardous Substances Data: 141171-72-4(Hazardous Substances Data)

Upstream product

• 62023-60-3 (2R,3S)-N-(benzyloxycarbonyl)-3-amino-2-hydroxy-4-phenylbutanoic acid 
• 62023-59-0 (2S,3S)-3-benzyloxycarbonylamino-2-hydroxy-4-phenylbutanoic acid 
• 128018-18-8 L-proline tert-butylamide 
• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 128018-17-7 Z-Pro-NH^tBu 
• 222848-56-8 (3S)-N-(benzyloxycarbonyl)-3-amino-2-hydroxy-4-phenylbutanoic acid 
• 114744-85-3 [(S)-1-(methoxy-methyl-carbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl 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 
• 172696-23-0 (2S,3S)-N-(benzyloxycarbonyl)-AHAP-(3-amino-2-hydroxy-4-phenylbutanoic acid) ethyl ester 

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 

Relevant articles and documents

HIV protease inhibitors

Combinatorial libraries of HIV and FIV protease inhibitors are characterized by alpha-keto amide or hydroxyethylamine core structures flanked by on one side by substituted pyrrolidines, piperidines, or azasugars and on the other side by phenylalanine, tyrosine, or substituted tyrosines. The libraries are synthesized via a one step coupling reaction. Highly efficacious drug candidates are identified by screening the libraries for binding and inhibitory activity against both HIV and FIV protease. Drug candidates displaying clinically useful activity against both HIV and FIV protease are identified as being potentially resistive against a loss of inhibitory activity due to development of resistant strains of HIV.

Synthesis of dipeptide-type human immunodeficiency virus (HIV) protease inhibitors with a binding unit to GP120

Some dipeptide-type human immunodeficiency virus (HIV) protease inhibitors derived from KNI-102, with a N-carbomethoxycarbonylprolyl- phenylalanine benzyl ester (CPF) moiety as a binding site to gp120, were synthesized. Compounds 11a showed 7 - 100 times higher HIV protease- inhibitory activity (11a; IC50 = 0.90 μg/ml, 1.1 μM) than the standard compound 3 or 4 (3; IC50 = 3.7 μg/ml, 7.7 μM, 4; IC50 = 75 μg/ml, 155 μM). Generally, the compounds substituted at the o-position of the phenoxyacetyl group 7a, 11a, 16a and 21a showed several times higher inhibitory activity than 3.

Synthesis and human immunodeficiency virus (HIV-1 protease inhibitory activity of tripeptide analogues containing a dioxoethylene moiety

Tripeptide analogues 2 and 3 containing a dioxoethylene moiety were designed based on the characteristic structure of the naturally occurring human immunodeficiency virus (HIV)-I protease inhibitors RPI-856 A, B, C and D (1). The compounds (2, 3) prepared showed high inhibitory activity, comparable to that of RPI-856 A, against HIV-1 protease in vitro.