164515-05-3

Basic information

• Product Name: (2R,3R,4S)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-3-hydroxy-2-<(4-methoxybenzyl)amino>-5-phenylpentanoic acid ethyl ester
• Synonyms: (2R,3R,4S)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-3-hydroxy-2-<(4-methoxybenzyl)amino>-5-phenylpentanoic acid ethyl ester
• CAS NO: 164515-05-3
• Molecular Weight: 472.582
• Mol File: 164515-05-3.mol

Chemical Properties

• CAS DataBase Reference: (2R,3R,4S)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-3-hydroxy-2-<(4-methoxybenzyl)amino>-5-phenylpentanoic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4S)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-3-hydroxy-2-<(4-methoxybenzyl)amino>-5-phenylpentanoic acid ethyl ester(164515-05-3)
• EPA Substance Registry System: (2R,3R,4S)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-3-hydroxy-2-<(4-methoxybenzyl)amino>-5-phenylpentanoic acid ethyl ester(164515-05-3)

Safety Data

• Hazardous Substances Data: 164515-05-3(Hazardous Substances Data)

Upstream product

• 2393-23-9 4-methoxy-benzylamine 
• 124818-94-6 ethyl (2E,4S)-4-[(tert-butoxycarbonyl)amino]-5-phenylpent-2-enoate 
• 72155-45-4 Boc-L-phenylalaninal 
• 66605-57-0 (S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol 

Downstream Products

• 353791-27-2 (2R,3R,4S)-4-((S)-2-Amino-3,3-dimethyl-butyrylamino)-3-hydroxy-2-(4-methoxy-benzylamino)-5-phenyl-pentanoic acid [(S)-1-(2-hydroxy-4-methoxy-benzylcarbamoyl)-2-methyl-propyl]-amide 
• 164514-61-8 {1-[1-benzyl-2-hydroxy-3-[1-(2-hydroxy-4-methoxy-benzylcarbamoyl)-2-methyl-propylcarbamoyl]-3-(4-methoxy-benzylamino)-propylcarbamoyl]-2,2-dimethyl-propyl}-carbamic acid tert-butyl ester 
• 164514-51-6 SDZ 283051 
• 164514-52-7 SDZ PRI-053 
• 154030-79-2 SDZ 283263 
• 161186-51-2 {(S)-1-[(1S,2R,3R)-3-{(S)-1-[(1H-Benzoimidazol-2-ylmethyl)-carbamoyl]-2-methyl-propylcarbamoyl}-1-benzyl-2-hydroxy-3-(4-methoxy-benzylamino)-propylcarbamoyl]-2,2-dimethyl-propyl}-carbamic acid benzyl ester 
• 172215-58-6 SDZ 283364 
• 256419-27-9 6(S)-benzyl-5(R)-t-butyl-dimethylsilyloxy-1,3-bis-(4-methoxybenzyl)-2-oxo-hexahydropyrimidine-4(R)-carboxylic acid 2-(4-methoxyphenyl)ethyl ester 
• 256419-22-4 6(S)-benzyl-5(R)-t-butyl-dimethylsilyloxy-3-(4-methoxybenzyl)-2-oxo-hexahydropyrimidine-4(R)-carboxylic acid 2-(4-methoxyphenyl)ethyl ester 
• 256419-14-4 1-allyl-6(S)-benzyl-5(R)-t-butyl-dimethylsilyloxy-3-(4-methoxybenzyl)-2-oxo-hexahydropyrimidine-4(R)-carboxylic acid ethyl ester 
• 256419-20-2 6(S)-benzyl-5(R)-t-butyl-dimethylsilyloxy-3-(4-methoxybenzyl)-2-oxo-hexahydropyrimidine-4(R)-carboxylic acid butyl ester 
• 256419-16-6 1-allyl-6(S)-benzyl-5(R)-t-butyldimethylsilyloxy-4(S)-hydroxymethyl-3-(4-methoxybenzyl)-2-oxo-hexahydropyrimidine 
• 256419-13-3 6(S)-benzyl-5(R)-t-butyl-dimethylsilyloxy-3-(4-methoxybenzyl)-2-oxo-hexahydropyrimidine-4(R)-carboxylic acid ethyl ester 

Relevant articles and documents

Structure-based optimisation of 2-aminobenzylstatine derivatives: Potent and selective inhibitors of the chymotrypsin-like activity of the human 20S proteasome

We have identified 2-aminobenzylstatine derivatives that inhibit non-covalently the chymotrypsin-like activity of the human 20S proteasome. A structure-based optimisation approach has allowed us to improve the potency of this structural class of proteasome inhibitors from micromolar to nanomolar level. The new derivatives showed good selectivity against the trypsin-like and post-glutamyl-peptide hydrolytic activities of this enzyme.

A new structural class of selective and non-covalent inhibitors of the chymotrypsin-like activity of the 20S proteasome

We describe the identification and in vitro characterization of a series of 2-aminobenzylstatine derivatives that inhibit non-covalently the chymotrypsin-like activity of the 20S proteasome. Our initial SAR data demonstrate that the 2-aminobenzylstatine core structure can effectively serve as the basis for designing potent, selective and non-covalent inhibitors of the chymotrypsin-like activity of the 20S proteasome.

Inhibitors of human immunodeficiency virus type 1 protease containing 2- aminobenzyl-substituted 4-amino-3-hydroxy-5-phenylpentanoic acid: Synthesis, activity, and oral bioavailability

Systematic modifications of HIV protease inhibitor (2R,3S,4S)-4- [[(benzyloxycarbonyl)-L-valyl]amino]-3-hydroxy-2-[(4-methoxybenzyl)amino]-5- (phenylpentanoyl)-L-valine 2-(aminomethyl)-benzimidazole amide led to a novel series of inhibitors with a shortened, modified carboxy terminus. Their synthesis, in vitro enzyme inhibitory data, and antiviral activities are reported. Of particular interest are derivatives featuring the (1S,2R)-1- amino-2-hydroxyindan moiety at the P2'-position since some of them exhibit substantial oral bioavailability in mice. The influence of aqueous solubility and structural parameters on the oral resorption of the inhibitors is discussed. Optimum enhancement of oral bioavailability was observed with L- tert-leucine in P2-position, resulting in the discovery of (2R,3S,4S)-4- [[(benzyloxycarbonyl)-L-tert-leucyl]amino]-3-hydroxy-2-[(4- methoxybenzyl)amino]-5-phenylpentanoic acid (1S,2R)-1-amino-2-hydroxyindan amide which combines high antiviral activity (IC50 = 250 nM) with a good pharmacokinetic profile (AUC = 82.5 μM · h at a dose of 125 mg/kg po in mice).

Inhibitors of HIV-1 proteinase containing 2-heterosubstituted 4-amino-3- hydroxy-5-phenylpentanoic acid: Synthesis, enzyme inhibition, and antiviral activity

A convenient procedure for the synthesis of 2-heterosubstituted statine derivatives as novel building blocks in HIV-protease inhibitors has been developed. The synthesis starts with protected L-phenylalaninols, which were converted to γ-amino α,β-unsatura