656236-30-5

Basic information

• Product Name: 6-Benzothiazolesulfonamide, N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl)-
• CAS NO: 656236-30-5
• Molecular Formula: C21H27N3O3S2
• Molecular Weight: 433.596
• Mol File: 656236-30-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 6-Benzothiazolesulfonamide, N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Benzothiazolesulfonamide, N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl)-(656236-30-5)
• EPA Substance Registry System: 6-Benzothiazolesulfonamide, N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl)-(656236-30-5)

Safety Data

• Hazardous Substances Data: 656236-30-5(Hazardous Substances Data)

Upstream product

• 183004-94-6 3-S-(N-tert-butyloxyformamido)-[2R-hydroxy-1-[(4-aminophenylsulfonyl)(2-methylpropyl)]amino]-4-phenylbutane 
• 183554-21-4 3-S-amino-2R-hydroxy-1-[(2-aminobenzothiazol-6-sulfonyl)(2-methylpropyl)amino]-4-phenylbutane 
• 159005-59-1 4-nitro-N-((2R(syn),3S)-3-(N-benzyloxycarbonylamino)-2-hydroxy-4-phenylbutyl)-N-isobutyl-benzenesulfonamide 
• 169280-56-2 4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 143224-62-8 (2R,3S)-3-benzyloxycarbonylamino-2-hydroxy-1-(N-isobutylamino)-4-phenylbutane 
• 183004-96-8 N-[(1S,2R)-3-[(6-benzothiazolylsulfonyl)-(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]-carbamic acid-1,1-dimethylethyl ester 

Downstream Products

• 918294-83-4 (3R)-N-[(1S,2R)-3-[(6-benzothiazolylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]-3-hydroxy-pentanamide 
• 918294-79-8 (2S)-2-(acetylamino)-N-[(1S,2R)-3-[(6-benzothiazolylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]-3-methyl-butanamide 
• 1026701-29-0 N-[(1S,2R)-3-[(6-benzothiazolylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]-1-cyclopropane-1,1-dicarboxamide 

Relevant articles and documents

Additivity in the analysis and design of HIV protease inhibitors

We explore the applicability of an additive treatment of substituent effects to the analysis and design of HIV protease inhibitors. Affinity data for a set of inhibitors with a common chemical framework were analyzed to provide estimates of the free energy contribution of each chemical substituent. These estimates were then used to design new inhibitors whose high affinities were confirmed by synthesis and experimental testing. Derivations of additive models by least-squares and ridge-regression methods were found to yield statistically similar results. The additivity approach was also compared with standard molecular descriptor-based QSAR; the latter was not found to provide superior predictions. Crystallographic studies of HIV protease-inhibitor complexes help explain the perhaps surprisingly high degree of substituent additivity in this system, and allow some of the additivity coefficients to be rationalized on a structural basis.

Discovery of novel benzothiazolesulfonamides as potent inhibitors of HIV-1 protease

The human immunodeficiency virus (HIV) has been shown to be the causative agent for AIDS. The HIV virus encodes for a unique aspartyl protease that is essential for the production of enzymes and proteins in the final stages of maturation. Protease inhibitors have been useful in combating the disease. The inhibitors incorporate a variety of isosteres including the hydroxyethylurea at the protease cleavage site. We have shown that the replacement of t-butylurea moiety by benzothiazolesulfonamide provided inhibitors with improved potency and antiviral activities. Some of the compounds have shown good oral bioavailability and half-life in rats. The synthesis of benzothiazole derivatives led us to explore other heterocycles. During the course of our studies, we also developed an efficient synthesis of benzothiazole-6-sulfonic acid via a two-step procedure starting from sulfanilamide.