159006-03-8

Basic information

• Product Name: Carbamic acid, [(1S,2R)-2-hydroxy-3-[[(4-methoxyphenyl)sulfonyl](2-methylpropyl)amino ]-1-(phenylmethyl)propyl]-, 1,1-dimethylethyl ester
• Synonyms: {(1S,2R)-1-Benzyl-2-hydroxy-3-[isobutyl-(4-methoxy-benzenesulfonyl)-amino]-propyl}-carbamic acid tert-butyl ester;((1S,2R)-1-benzyl-2-hydroxy-3-{[4-methoxybenzenesulfonyl]isobutylamino}propyl)carbamic acid tert-butyl ester;N-[(1S,2R)-2-hydroxy-3-[[(4-methoxyphenyl)sulfonyl](2-methylpropyl)amino]-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester;N-[(1S,2R)-2-hydroxy-3-[[(4-methoxyphenyl)sulfonyl](2-methylpropyl)amino]-1-(phenylmethyl)propyl]-carbamic acid tert-butyl ester;N-[(1S,2R)-1-benzyl-2-hydroxy-3-[isobutyl[(4-methoxyphenyl)sulfonyl]amino]propyl]carbamic acid tert-butyl ester
• CAS NO: 159006-03-8
• Molecular Formula: C26H38N2O6S
• Molecular Weight: 506.664
• Mol File: 159006-03-8.mol
• Article Data: 24

Chemical Properties

• CAS DataBase Reference: Carbamic acid, [(1S,2R)-2-hydroxy-3-[[(4-methoxyphenyl)sulfonyl](2-methylpropyl)amino ]-1-(phenylmethyl)propyl]-, 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [(1S,2R)-2-hydroxy-3-[[(4-methoxyphenyl)sulfonyl](2-methylpropyl)amino ]-1-(phenylmethyl)propyl]-, 1,1-dimethylethyl ester(159006-03-8)
• EPA Substance Registry System: Carbamic acid, [(1S,2R)-2-hydroxy-3-[[(4-methoxyphenyl)sulfonyl](2-methylpropyl)amino ]-1-(phenylmethyl)propyl]-, 1,1-dimethylethyl ester(159006-03-8)

Safety Data

• Hazardous Substances Data: 159006-03-8(Hazardous Substances Data)

Upstream product

• 1053517-88-6 (2S,3S)-3-Amino-1-benzyloxy-4-phenyl-butan-2-ol 
• 193953-56-9 (4S,5S)-4-benzyl-5-benzyloxymethyl-1,3-oxazolidin-2-one 
• 193953-57-0 ((1S,2S)-1-Benzyl-3-benzyloxy-2-hydroxy-propyl)-carbamic acid tert-butyl ester 
• 78-81-9 isobutylamine 
• 98760-08-8 (1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester 
• 98-68-0 4-methoxy-phenyl-sulphonyl chloride 
• 98760-08-8 (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane 
• 149451-80-9 (2S,3S)-3-(t-butoxycarbonylamino)-4-phenylbutane-1,2-diol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 160232-08-6 (2R,3S)-3-tert-butoxycarbonylamino-1-isobutylamino-4-phenyl-2-butanol 

Downstream Products

• 1321531-13-8 (3aS,5R,6aR)-3-oxohexahydro-2H-cyclopenta[b]furan-5-yl [(2S,3R)-3-hydroxy-4-(N-isobutyl-4-methoxyphenylsulfonamido)-1-phenylbutan-2-yl]carbamate 
• 1365655-68-0 GRL-0289A 
• 1365655-67-9 GRL-0249A 
• 1262482-49-4 (3aR,4S,7aR)-octahydro-1H-inden-4-yl-(2S,3R)-3-hydroxy-4-(N-isobutyl-4-methoxyphenylsulfonamido)-1-phenylbutan-2-yl carbamate 
• 1075209-49-2 GRL-0476 

Relevant articles and documents

Accessing HIV-1 Protease Inhibitors through Visible-Light-Mediated Sequential Photocatalytic Decarboxylative Radical Conjugate Addition-Elimination-Oxa-Michael Reactions

A photocatalytic decarboxylative radical conjugate addition-elimination-oxa-Michael reaction of hydroxyalkylated carboxylic acids with cyclopentenones is developed to construct diverse cyclopentanonyl-fused functionalized 5-7 membered cyclic ethers. The stereoselective synthetic strategy is amenable to substructural variation, establishing a direct total synthetic route to two diastereomers of C3-amino cyclopentyltetrahydrofuranyl-derived potent HIV-1 protease inhibitors with low nanomolar IC50 values.

Design and evaluation of novel piperidine HIV-1 protease inhibitors with potency against DRV-resistant variants

A novel class of HIV-1 protease inhibitors with flexible piperidine as the P2 ligand was designed with the aim of improving extensive interactions with the active subsites. Many inhibitors exhibited good to excellent inhibitory effect on enzymatic activity and viral infectivity. In particular, inhibitor 3a with (R)-piperidine-3-carboxamide as the P2 ligand and 4-methoxybenzenesulfonamide as the P2’ ligand showed an enzyme Ki value of 29 pM and antiviral IC50 value of 0.13 nM, more than six-fold enhancement of activity compared to DRV. Furthermore, there was no significant change in potency against DRV-resistant mutations and HIV-1NL4?3 variant for 3a. Besides, inhibitor 3a exhibited potent antiviral activity against subtype C variants with low nanomole EC50 values. In addition, the molecular modeling revealed important hydrogen bonds and other favorable van der Waals interactions with the backbone atoms of the protease and provided insight for designing and optimizing more potent HIV-1 protease inhibitors.

Preliminary SAR and biological evaluation of potent HIV-1 protease inhibitors with pyrimidine bases as novel P2 ligands to enhance activity against DRV-resistant HIV-1 variants

Introducing pyrimidine bases, the basic components of nucleic acid, to P2 ligands might enhance the potency of Human Immunodeficiency Virus-1 (HIV-1) protease inhibitors because of the carbonyl and amino groups promoting the formation of extensive hydrogen bonding interactions. In this work, we provide evidence that inhibitor 10e, with N-2-(2,4-Dioxo-3,4-dihydropyrimidin-1(2H)-yl) acetamide as the P2 ligand and a 4-methoxylphenylsulfonamide as the P2′ ligand, displayed remarkable enzyme inhibitory and antiviral activity, with the IC50 2.53 nM in vitro and a promising inhibition ratio with 68% against wild-type HIV-1 in vivo, with low cytotoxicity. This inhibitor also exhibited appreciable antiviral activity against DRV-resistant HIV-1 variants, which was of great value for further study.