5398-96-9

Basic information

• Product Name: BENZENESULFONYLAMINO-ACETIC ACID
• Synonyms: Phenylsulfonylaminoacetic acid;2-(PhenylsulfonaMido)acetic acid
• CAS NO: 5398-96-9
• Molecular Formula: C₈H₉NO₄S
• Molecular Weight: 215.23
• Mol File: 5398-96-9.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 426.9°Cat760mmHg
• Flash Point: 212°C
• Appearance: /
• Density: 1.423g/cm³
• Vapor Pressure: 4.75E-08mmHg at 25°C
• Refractive Index: 1.577
• CAS DataBase Reference: BENZENESULFONYLAMINO-ACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: BENZENESULFONYLAMINO-ACETIC ACID(5398-96-9)
• EPA Substance Registry System: BENZENESULFONYLAMINO-ACETIC ACID(5398-96-9)

Safety Data

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39
• Hazardous Substances Data: 5398-96-9(Hazardous Substances Data)

Usage

General Description

Benzene sulfonylaminoacetic acid is a chemical compound with the molecular formula C8H9NO4S. It is a derivative of aminoacetic acid, with a benzene sulfonamide group attached to the amino group. BENZENESULFONYLAMINO-ACETIC ACID is used in the synthesis of various pharmaceuticals and agrochemicals, particularly in the production of antibiotics and antiviral drugs. Benzene sulfonylaminoacetic acid has also been studied for its potential use in the treatment of cardiovascular diseases and as an inhibitor of the enzyme aldose reductase, which is implicated in diabetic complications. Additionally, it is used as a precursor in the synthesis of dyes and pigments. However, it is important to handle this chemical with care as it may pose risks to human health and the environment.

InChI:InChI=1/C8H9NO4S/c10-8(11)6-9-14(12,13)7-4-2-1-3-5-7/h1-5,9H,6H2,(H,10,11)

Upstream product

• 98-10-2 benzenesulfonamide 
• 3926-62-3 sodium monochloroacetic acid 
• 79-11-8 chloroacetic acid 
• 98-09-9 benzenesulfonyl chloride 
• 56-40-6 glycine 
• 873-55-2 sodium benzenesulfonate 
• 7647-01-0 hydrogenchloride 
• 64-18-6 formic acid 
• 64-69-7 Iodoacetic acid 
• 5661-14-3 N-(phenylsulfonyl)acetamide 
• 970-88-7 2,4-dinitrophenyl benzenesulfonate 
• 34545-74-9 N-Phenylsulfonylglycine tert-butyl ester 
• 86674-20-6 C₈H₈N₂O₆S 

Downstream Products

• 6019-19-8 N-benzenesulfonyl-N-butyl-glycine 
• 59724-82-2 N-benzenesulfonyl-N-phenyl-glycine 
• 99072-39-6 N-benzenesulfonyl-glycine cyanomethyl ester 
• 100137-72-2 (N-benzenesulfonyl-glycyloxy)-acetic acid ethyl ester 
• 101106-47-2 (N-benzenesulfonyl-glycyloxy)-malonic acid diethyl ester 
• 859980-85-1 N-allyl-N-benzenesulfonyl-glycine 
• 276695-37-5 N-benzenesulfonyl-N-benzyl-glycine 
• 99856-37-8 N-benzenesulfonyl-glycine allyl ester 
• 412342-13-3 N-benzenesulfonyl-N-methallyl-glycine 
• 101116-07-8 N-benzenesulfonyl-glycine cyclohexyl ester 
• 98-09-9 benzenesulfonyl chloride 
• 351333-19-2 methyl N-[phenylsulphonyl-glycyl]anthranilate 
• 1160366-92-6 (S)-N-[[3-[3-fluoro-4-[4-[2-(phenylsulfonamido)acetyl]piperazin-1-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide 
• 1313238-68-4 N-(3-methyl-4-oxo-4H-[1,3,4]thiadiazolo[2,3-c][1,2,4]triazin-7-ylmethyl)benzenesulfonamide 

Relevant articles and documents

Synthesis, crystal structure and antibacterial activity of Ca(II) complex with 2-(Phenylsulfonamido)acetic acid

A new ligand 2-(phenylsulfonamido)acetic acid (L) and its Ca(II) complex have been synthesized and characterized by elemental analysis, IR spectroscopy and single-crystal X-ray diffraction. The results showed that the complex formed one dimensional chaine

A new one-pot synthesis of pseudopeptide connected to sulfonamide: Via the tandem N -sulfonylation/Ugi reactions

In this study, an efficient one-pot reaction is reported for the synthesis of a new class of pseudopeptide connected to sulfonamide via a tandem N-sulfonylation/Ugi four-component reaction (Ugi-4CR) strategy under mild conditions in high yields. This five-component reaction strategy is carried out by readily available starting materials, sulfonyl chlorides, glycines, benzylamines, benzaldehydes, and isocyanides, in ethanol/water at room temperature. The generation of carboxylic acid that is a key component in Ugi-4CR could be accomplished by performing the N-sulfonylation reaction, and it could be used in the next step without further purification. The as-synthesized compounds that are constructed from pseudopeptide connected to a sulfonamide scaffold have the potential to be used in designing modern drugs with the highly desirable feature.

Development of Piperazinediones as dual inhibitor for treatment of Alzheimer's disease

Novel multifunctional 3,6-Diphenyl-1,4-bis(phenylsulfonyl)piperazine-2,5-dione derivatives were designed and synthesized for the treatment of Alzheimer's disease (AD). The designed scaffold has blood brain barrier penetrating ability, acetylcholinesterase (AChE) and matrix metalloproteinase-2 (MMP-2) inhibition potential. Compounds 52 and 46 showed very significant inhibition against AChE, IC50 = 32.45 ± 0.044, 28.65 ± 0.029, BuChE, IC50 = 157.95 ± 0.264, 160.58 ± 0.082 and MMP-2, IC50 = 36.83 ± 0.015, 19.57 ± 0.005 (nM). In the enzyme kinetics study, lead molecule 46 showed non-competitive inhibition of AChE with Ki = 7 nM and competitive inhibition of MMP-2 with Ki = 20 nM. Compounds 52 and 46 inhibited AChE-induced Aβ aggregation at 20 μM. The compounds also exhibited in-vitro antioxidant potential in DPPH assay. Further, compound 46 was found to be a promising neuroprotective agent in MC65 cells. Lead molecule 46 significantly enhanced working memory in scopolamine induced amnesia animal model at dose of 5 mg/kg dose. The mitochondrial membrane potential was restored in animals when treated with compounds 52 and 46.

Synthesis, characterization, molecular docking and in?vitro antimalarial properties of new carboxamides bearing sulphonamide

Sulphonamides and carboxamides have shown large number of pharmacological properties against different types of diseases among which is malaria. Twenty four new carboxamide derivatives bearing benzenesulphonamoyl alkanamides were synthesized and investigated for their in silico and in?vitro antimalarial and antioxidant properties. The substituted benzenesulphonyl chlorides (1a-c) were treated with various amino acids (2a-h) to obtain the benzenesulphonamoyl alkanamides (3a-x) which were subsequently treated with benzoyl chloride to obtain the N-benzoylated derivatives (5a-f, i-n and q-v). Further reactions of the N-benzoylated derivatives or proline derivatives with 4-aminoacetophenone (6) using boric acid as a catalyst gave the sulphonamide carboxamide derivatives (7a-x) in excellent yields. The in?vitro antimalarial studies showed that all synthesized compounds had antimalarial property. Compound 7k, 7c, 7l, 7s, and 7j had mean MIC value of 0.02, 0.03, 0.05, 0.06 and 0.08?μM respectively comparable with chloroquine 0.06?μM. Compound 7c was the most potent antioxidant agent with IC50 value of 0.045?mM comparable with 0.34?mM for ascorbic acid. In addition to the successful synthesis of the target molecules using boric acid catalysis, the compounds were found to have antimalarial and antioxidant activities comparable with known antimalarial and antioxidant drugs. The class of compounds reported herein have the potential of reducing oxidative stress arising from malaria parasite and chemotherapeutic agent used in the treatment of malaria.