251105-80-3

Basic information

• Product Name: Benzenesulfonamide, N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl)-4-nitro -
• CAS NO: 251105-80-3
• Molecular Formula: C20H27N3O5S
• Molecular Weight: 421.517
• Mol File: 251105-80-3.mol
• Article Data: 21

Chemical Properties

• CAS DataBase Reference: Benzenesulfonamide, N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl)-4-nitro -(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenesulfonamide, N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl)-4-nitro -(251105-80-3)
• EPA Substance Registry System: Benzenesulfonamide, N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl)-4-nitro -(251105-80-3)

Safety Data

• Hazardous Substances Data: 251105-80-3(Hazardous Substances Data)

Usage

Description

Benzenesulfonamide, N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl)-4-nitro is a complex chemical compound that features a benzene ring and a sulfonamide functional group. It is enriched with an amino group, a hydroxy group, a phenyl group, and a butyl group, which contribute to its unique properties. Benzenesulfonamide,
N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl)-4-nitro
-'s stereochemistry is defined by its (2R,3S) configuration, which specifies the precise arrangement of its substituent groups. The presence of a nitro group suggests a high level of reactivity, and its structure hints at potential pharmaceutical or biological applications, possibly as a drug or a component in medicinal products.

Uses

Used in Pharmaceutical Industry:
Benzenesulfonamide, N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl)-4-nitro is used as a potential drug candidate for various therapeutic applications due to its complex structure and reactivity. Its specific stereochemistry and functional groups may allow it to interact with biological targets in ways that could be beneficial for treating certain diseases or conditions.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, this compound serves as a valuable research tool for understanding the structure-activity relationships of sulfonamide-based drugs. Its unique features can provide insights into the design and development of new pharmaceuticals with improved efficacy and selectivity.
Used in Chemical Synthesis:
The reactivity of Benzenesulfonamide, N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl)-4-nitro, particularly due to the presence of the nitro group, makes it a useful intermediate in the synthesis of other complex organic molecules. It can be employed in various chemical reactions to produce a range of compounds with diverse applications in different industries.

Upstream product

• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 136465-89-9 (2S)-2-[1'(S)-1-azido-2-phenylethyl]oxirane 
• 78571-81-0 (3-benzyloxiran-2-yl)methanol 
• 42238-15-3 (2E)-4-phenylbut-2-en-1-ol 
• 54966-42-6 ethyl 3-benzylacrylate 
• 143224-62-8 (2R,3S)-3-benzyloxycarbonylamino-2-hydroxy-1-(N-isobutylamino)-4-phenylbutane 
• 128018-44-0 N-benzyloxycarbonyl-3(S)-amino-1,2(S)epoxy-4-phenylbutane 
• 160232-08-6 (2R,3S)-3-tert-butoxycarbonylamino-1-isobutylamino-4-phenyl-2-butanol 
• 98760-08-8 (1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester 
• 78-81-9 isobutylamine 
• 159005-59-1 4-nitro-N-((2R(syn),3S)-3-(N-benzyloxycarbonylamino)-2-hydroxy-4-phenylbutyl)-N-isobutyl-benzenesulfonamide 
• 191226-98-9 [(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester 
• 85531-71-1 (3-benzyloxiran-2-yl)methanol 
• 89840-80-2 N-isobutyl-4-nitrobenzenesulfonamide 

Downstream Products

• 264884-01-7 N-{(1S,2R)-1-Benzyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-2-(2,6-dimethyl-phenoxy)-acetamide 
• 919081-52-0 2-oxo-3-phenyl-oxazolidine-5-carboxylic acid {1-benzyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-amide 
• 919081-33-7 2-oxo-3-phenyl-oxazolidine-5-carboxylic acid {1-benzyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-amide 
• 919081-34-8 3-(3-fluoro-phenyl)-2-oxo-oxazolidine-5-carboxylic acid {1-benzyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-amide 
• 919081-38-2 3-(4-acetyl-phenyl)-2-oxo-oxazolidine-5-carboxylic acid {1-benzyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-amide 
• 919081-37-1 3-(3-acetyl-phenyl)-2-oxo-oxazolidine-5-carboxylic acid {1-benzyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-amide 
• 919081-35-9 3-(3,4-difluoro-phenyl)-2-oxo-oxazolidine-5-carboxylic acid {1-benzyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-amide 
• 919081-36-0 2-oxo-3-(3-trifluoromethyl-phenyl)-oxazolidine-5-carboxylic acid {1-benzyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-amide 
• 1309164-56-4 N-((2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl)-2-((S)-tetrahydrofuran-3-yloxy)acetamide 
• 1309164-51-9 N-((2S,3R)-3-hydroxy-4-(N-isobutyl-4-nitrophenylsulfonamido)-1-phenylbutan-2-yl)-2-((S)-tetrahydrofuran-3-yloxy)acetamide 
• 1309164-70-2 1-ethyl-N-((2S,3R)-3-hydroxy-4-(N-isobutyl-4-nitrophenylsulfonamido)-1-phenylbutan-2-yl)cyclopentanecarboxamide 
• 161814-49-9 amprenavir 
• 169280-56-2 4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide 
• 1348180-72-2 amprenavir 

Relevant articles and documents

Preparation method of chiral phenbutamol sulfonamide compound, intermediate for preparing chiral phenbutamol sulfonamide compound and preparation method of chiral phenbutamol sulfonamide compound

The invention discloses a preparation method of a chiral phenbutamol sulfonamide compound, which comprises the following steps: carrying out substitution reaction on a compound A, establishing a chiral center by using ketoreductase, and carrying out amidation and Hofmann degradation to obtain the chiral phenbutamol sulfonamide compound, the structural formula of the compound A is as follows: Q1 and Q2 are independently selected from heteroatom groups containing one or more of nitrogen, oxygen and sulfur, or H, or Q1 and Q2 are connected to form a ring, and R1 is selected from alkyl with the carbon atom number of 1-6. The preparation method provided by the invention has the advantages of simple steps, few reaction steps, mild reaction of each step, high safety coefficient and low production cost.

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.

Rational design and Structure?Activity relationship of coumarin derivatives effective on HIV-1 protease and partially on HIV-1 reverse transcriptase

Since dual inhibitors may yield lower toxicity and reduce the likelihood of drug resistance, as well as inhibitors of HIV-1 PR and RT constitute the core of chemotherapy for AIDS treatment, we herein designed and synthesized new coumarin derivatives characterized by various linkers that exhibited excellent potency against PR and a weak inhibition of RT. Among which, compounds 6f and 7c inhibited PR with IC50 values of 15.5 and 62.1 nM, respectively, and weakly affected also RT with IC50 values of 241.8 and 188.7 μM, respectively, showing the possibility in the future of developing dual HIV-1 PR/RT inhibitors. Creative stimulation for further research of more potent dual HIV-1 inhibitors was got according to the molecular docking studies.