553644-88-5

Basic information

• Product Name: Carbamic acid, [(1S,2R)-3-[[(4-acetylphenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1 -(phenylmethyl)propyl]-, 1,1-dimethylethyl ester
• CAS NO: 553644-88-5
• Molecular Formula: C27H38N2O6S
• Molecular Weight: 518.675
• Mol File: 553644-88-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Carbamic acid, [(1S,2R)-3-[[(4-acetylphenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1 -(phenylmethyl)propyl]-, 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [(1S,2R)-3-[[(4-acetylphenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1 -(phenylmethyl)propyl]-, 1,1-dimethylethyl ester(553644-88-5)
• EPA Substance Registry System: Carbamic acid, [(1S,2R)-3-[[(4-acetylphenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1 -(phenylmethyl)propyl]-, 1,1-dimethylethyl ester(553644-88-5)

Safety Data

• Hazardous Substances Data: 553644-88-5(Hazardous Substances Data)

Upstream product

• 75-16-1 methylmagnesium bromide 
• 854745-35-0 (acetyloxy)(4-{[{(2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-4-phenylbutyl}(isobutyl)amino]sulfonyl}phenyl)methyl Acetate 
• 98760-08-8 (1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester 
• 1788-10-9 4-Acetylbenzenesulfonyl chloride 
• 160232-08-6 (2R,3S)-3-tert-butoxycarbonylamino-1-isobutylamino-4-phenyl-2-butanol 

Downstream Products

• 695815-04-4 4-acetyl-N-(3-amino-2-hydroxy-4-phenyl-butyl)-N-isobutyl-benzenesulfonamide 

Relevant articles and documents

Design, Synthesis, Biological Evaluation, and X-ray Studies of HIV-1 Protease Inhibitors with Modified P2′ Ligands of Darunavir

The structure-based design, synthesis, and biological evaluation of a series of nonpeptidic HIV-1 protease inhibitors with rationally designed P2′ ligands are described. The inhibitors are designed to enhance backbone binding interactions, particularly at

Discovery and selection of TMC114, a next generation HIV-1 protease inhibitor

The screening of known HIV-1 protease inhibitors against a panel of multi-drug-resistant viruses revealed the potent activity of TMC126 on drug-resistant mutants. In comparison to amprenavir, the improved affinity of TMC126 is largely the result of one extra hydrogen bond to the backbone of the protein in the P2 pocket. Modification of the substitution pattern on the phenylsulfonamide P2′ substituent of TMC126 created an interesting SAR, with the close analogue TMC114 being found to have a similar antiviral activity against the mutant and the wild-type viruses. X-ray and thermodynamic studies on both wild-type and mutant enzymes showed an extremely high enthalpy driven affinity of TMC114 for HIV-1 protease. In vitro selection of mutants resistant to TMC114 starting from wild-type virus proved to be extremely difficult; this was not the case for other close analogues. Therefore, the extra H-bond to the backbone in the P2 pocket cannot be the only explanation for the interesting antiviral profile of TMC114. Absorption studies in animals indicated that TMC114 has pharmacokinetic properties comparable to currently approved HIV-1 protease inhibitors.