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

• 98760-08-8 (1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 78-81-9 isobutylamine 
• 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 
• 193953-57-0 ((1S,2S)-1-Benzyl-3-benzyloxy-2-hydroxy-propyl)-carbamic acid tert-butyl ester 
• 193953-56-9 (4S,5S)-4-benzyl-5-benzyloxymethyl-1,3-oxazolidin-2-one 
• 1053517-88-6 (2S,3S)-3-Amino-1-benzyloxy-4-phenyl-butan-2-ol 
• 160232-08-6 (2R,3S)-3-tert-butoxycarbonylamino-1-isobutylamino-4-phenyl-2-butanol 

Downstream Products

• 1365655-68-0 GRL-0289A 
• 1365655-67-9 GRL-0249A 
• 918542-76-4 3-(3-acetyl-phenyl)-2-oxo-oxazolidine-5-carboxylic acid {1-benzyl-2-hydroxy-3-[isobutyl-(4-methoxy-benzenesulfonyl)-amino]-propyl}-amide 
• 159005-71-7 N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-isobutyl-4-methoxybenzenesulfonamide 

Relevant articles and documents

Design and biological evaluation of cinnamic and phenylpropionic amide derivatives as novel dual inhibitors of HIV-1 protease and reverse transcriptase

Upon the basis of both possible ligand-binding site interactions and the uniformity of key residues in active sites, a novel class of HIV-1 PR/RT dual inhibitors was designed and evaluated. Cinnamic acids or phenylpropionic acids with more flexible chain and smaller steric hindrance were introduced into the inhibitors, giving rise to significant improvement in HIV-1 RT inhibitory activity by one or two orders of magnitude, with comparable or even improved potency against PR at the same time, compared with coumarin anologues in our previous studies. Among these inhibitors, 38d displayed a 19-fold improvement in anti-PR activity with IC50 value of 0.081 nM compared to the control DRV. In addition, inhibitor 38c exhibited an excellent anti-RT IC50 value of 0.43 μM, only a 4.7-fold less potent activity than the control EFV. More significantly, the disparate ratio between HIV-1 PR and RT inhibition became more reasonable with ratio of 1: 10.4, just as 37b. Furthermore, the assays on HIV-1 late stage and early stage supported the rationality of designing dual inhibitors. The SAR data as well as molecular modeling studies provided new insight for further optimization of more potent HIV-1 PR/RT dual inhibitors.

Nitrogen-containing heterocyclic amino derivative, preparation method thereof and anti-HIV-1 medicine

The invention provides a nitrogen-containing heterocyclic ring amino derivative, a preparation method thereof and an anti-HIV-1 medicine, and belongs to the technical field of medicine application. The nitrogen-containing heterocyclic ring amino derivative provided by the invention can interfere with the process of hydrolyzing Gap and Gap-Pol precursor polyprotein by HIV-1 protease, and has high HIV-1 protease inhibitory activity; meanwhile, the nitrogen-containing heterocyclic ring amino derivative provided by the invention has remarkable inhibitory activity on wild type anti-HIV-1 medicine strains and high anti-DRV-medicine strains, has low cytotoxicity, and has a good application prospect as an anti-AIDS medicine.

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.