4816-81-3

Usage

Uses

Used in Chemical Research:
2-(Toluene-4-sulfonylamino)-propionic acid is used as a research compound for understanding its properties and potential applications in various scientific fields. Its unique structure allows for the exploration of its interactions and reactivity with other molecules.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 2-(Toluene-4-sulfonylamino)-propionic acid is used as a key intermediate in the synthesis of more complex molecules with potential therapeutic applications. Its functional groups can be manipulated to create new drug candidates with desired pharmacological properties.
Used in Material Science:
2-(Toluene-4-sulfonylamino)-propionic acid is employed as a building block in the development of new materials with specific properties, such as improved stability, reactivity, or biocompatibility. Its incorporation into material structures can lead to advancements in areas like polymer chemistry and materials engineering.
Used in Biochemistry:
In biochemistry, 2-(Toluene-4-sulfonylamino)-propionic acid is used as a component in the design of novel biomolecules, such as enzymes or receptors, with tailored functions. Its presence in these molecules can influence their interactions with other biological entities, potentially leading to new insights in biological processes and mechanisms.

InChI:InChI=1/C10H13NO4S/c1-7-3-5-9(6-4-7)16(14,15)11-8(2)10(12)13/h3-6,8,11H,1-2H3,(H,12,13)/p-1/t8-/m1/s1

Upstream product

• 56-41-7 L-alanin 
• 104-15-4 toluene-4-sulfonic acid 
• 598-72-1 2-Bromopropionic acid 
• 98-59-9 p-toluenesulfonyl chloride 
• 338-69-2 D-Alanine 
• 87023-89-0 N-(1-(3,5-dimethyl-1H-pyrazol-1-yl)-1-oxopropan-2-yl)-4-methylbenzenesulfonamide 
• 302-72-7 rac-Ala-OH 
• 134340-62-8 N-(1-furan-2-yl-ethyl)-4-methyl-benzenesulfonamide 
• 135822-87-6 (E)-N-(furan-2-ylmethylene)-4-methylbenzenesulfonamide 
• 134452-27-0 (S)-N-tosyl-α'-methyl-α-furfuryl amine 

Downstream Products

• 65919-32-6 N-(toluene-4-sulfonyl)-L-alanine thiazol-2-ylamide 
• 56271-34-2 (S)-2-(4-methylbenzenesulfonylamino)propionyl chloride 
• 100132-60-3 (S)-2-(toluene-4-sulfonamido)propan-1-ol 
• 80613-79-2 3-(N-tosyl-L-Ala)aminocoumarin 
• 78768-26-0 (S)-N-Phenazin-2-yl-2-(toluene-4-sulfonylamino)-propionamide 
• 91645-74-8 ethyl (S)-2-(N-p-toluenesulfonylamino)propanoate 
• 186039-97-4 (2S)-2-N-tosylamino-6-hepten-3-one 
• 78853-84-6 (S)-4-Methyl-3-(toluene-4-sulfonyl)-oxazolidin-5-one 
• 267885-95-0 1-(p-Toluenesulphonyl)-5-methyl-2-thiohydantoin 
• 336613-30-0 1,3-di(N^α-tosyl-L-alanylamido)propane 
• 336613-32-2 1,4-di(N^α-tosyl-L-alanylamido)butane 
• 592523-48-3 Acetic acid (Z)-4-{benzyl-[(S)-2-(toluene-4-sulfonylamino)-propionyl]-amino}-but-2-enyl ester 
• 849363-50-4 (CH₃)C₂HO₂B(C₆H₅)N(SO₂-p-tolyl) 

Relevant academic research and scientific papers

Silver-Catalyzed C(sp3)-H Sulfonylation for the Synthesis of Benzyl Sulfones Using Toluene Derivatives and α-Amino Acid Sulfonamides

We describe a simple and practical protocol for the synthesis of benzyl sulfones using readily available toluene derivatives and α-amino acid sulfonamides. The reaction proceeds to afford a broad range of benzyl sulfones in moderate to high yields under silver catalysis. The mechanism possibly involves a Minisci-type formation of α-aminoalkyl radical, homolytic cleavage of a N-S bond to generate a sulfonyl radical, and coupling of sulfonyl radical with a benzyl radical formed via hydrogen abstraction by sulfate anion radical. The practicality of the present reaction is demonstrated by a gram-scale synthesis and one-step synthesis of anticancer-active compound. The mechanism studies are conducted using radical scavengers and deuterated toluene.

Access to Optically Pure Benzosultams by Superelectrophilic Activation

Through superacid activation, N-(arenesulfonyl)-aminoalcohols derived from readily available ephedrines or amino acids undergo an intramolecular Friedel-Crafts reaction to afford enantiopure benzosultams bearing two adjacent stereocenters in high yields with fully controlled diastereoselectivity. Low-temperature NMR spectroscopy demonstrated the crucial role played by the conformationally restricted chiral dicationic intermediates.

Synthesis, molecular docking and pharmacological investigation of some 4-methylphenylsulphamoyl carboxylic acid analogs

Compounds bearing sulphonyl and amino acid moieties are considered the basis for sulfa drug development. The synthesis of 4-methylphenylsulphamoyl carboxylic acids and the evaluation of their pharmacological activities are reported. The synthesis of these

Synthesis and biological evaluation of alanine derived bioactive P-toluenesulphonamide analogs

Sulphonamides and carboxamides have great pharmacological importance. The purpose of the study was to synthesize alanine-derived bioactive sulphonamides bearing carboxamides and evaluate their biological activi-ties. The reaction of p-toluenesulphonyl chloride with L-alanine afforded compound 1, which was acetylated to obtain compound 2. The chlorina-tion and ammonolysis of compound 2 gave the carboxamide backbone (3) which was coupled with aryl/heteroaryl halides to afford the hybrid compounds 4, 5 and 6. Structures were confirmed by FTIR,1 H-NMR,13 C-NMR spectra and elemental analytical data. The in vitro antimicrobial properties were determined by agar dilution, and the antioxidant properties were also investigated. Molecular docking interactions of the analogues were determined using PyRx. Compounds 4, 5 and 6 exhibited excellent in vitro antimi-crobial properties in the range of 0.5-1.0mg/ml while compounds 1and 2 had half-maximal inhibitory concentration (IC50) of 1.11±0.15μg/ml and 1.12±0.13μg/ml respectively. For the molecular docking studies, compounds 5 and 6 displayed the best antitrypanosomal activity with binding affinities of-13.95 and-13.51kcal/mol respectively while compound 4 showed the highest in silico antimalarial activity having binding affinity of-11.95kcal/mol. All the alanine derived sulphonamides were observed to be potential antimicrobial, antioxidant, antitrypanosomal and antimalarial agents following the biological activities studies.

Synthesis and Structure-Activity Relationships of Arylsulfonamides as AIMP2-DX2 Inhibitors for the Development of a Novel Anticancer Therapy

AIMP2-DX2, a splicing variant of AIMP2, is up-regulated in lung cancer, possesses oncogenic activity, and results in tumorigenesis. Specifically inhibiting the interaction between AIMP2-DX2 and HSP70 to suppress AIMP2-DX2-dependent cancers with small molecules is considered a promising avenue for cancer therapeutics. Optimization of hit BC-DXI-04 (IC50 = 40.1 μM) provided new potent sulfonamide based AIMP2-DX2 inhibitors. Among these, BC-DXI-843 showed improved inhibition against AIMP2-DX2 (IC50 = 0.92 μM) with more than 100-fold selectivity over AIMP2 in a luciferase assay. Several binding assays indicated that this compound effectively induces cancer cell apoptosis by specifically interrupting the interaction between DX2 and HSP70, which leads to the degradation of DX2 via Siah1-mediated ubiquitination. More importantly, BC-DXI-843 demonstrated in vivo efficacy in a tumor xenograft mouse model (H460 cells) at a dosage of 50 mg/kg, suggesting it as a promising lead for development of novel therapeutics targeting AIMP2-DX2 in lung cancer.

Synthesis and hetero-Diels-Alder reactions of enantiomerically pure dihydro-1: H -azepines

Thermolysis of enantiomerically pure 3-substituted 7,7-dihalo-2-azabicyclo[4.1.0]heptanes in the presence of K2CO3 gives in good yields 2-alkyl-6-halo-1-tosyl-2,3-dihydro-1H-azepines. These undergo highly stereoselective [4+2] cycloaddition reactions with heterodienophiles and arylation/alkenylation under Suzuki conditions.

New peptide derived antimalaria and antimicrobial agents bearing sulphonamide moiety

Fourteen novel dipeptide carboxamide derivatives bearing benzensulphonamoyl propanamide were synthesized and characterized using 1H NMR, 13C NMR, FTIR and MS spectroscopic techniques. In vivo antimalarial and in vitro antimicrobial studies were carried out on these synthesized compounds. Molecular docking, haematological analysis, liver and kidney function tests were also evaluated to assess the effect of the compounds on the organs. At 200 mg/kg body weight, 7i inhibited the multiplication of the parasite by 81.38% on day 12 of post-treatment exposure. This was comparable to the 82.34% reduction with artemisinin. The minimum inhibitory concentration (MIC) in μM ranged from 0.03 to 2.34 with 7h having MIC of 0.03 μM against Plasmodium falciparium. The in vitro antibacterial activity of the compounds against some clinically isolated bacteria strains showed varied activities with some of the new compounds showing better activities against the bacteria and the fungi more than the reference drug ciprofloxacin and fluconazole.

Iodine-Catalyzed Synthesis of Chiral 4-Imidazolidinones Using α-Amino Acid Derivatives via Dehydrogenative N-H/C(sp3)-H Coupling

An efficient method for the asymmetric synthesis of 4-imidazolidinones via an iodine-catalyzed intramolecular N-H/C(sp3)-H activation of readily available and abundant feedstocks, amino acids, and amines is described. The reaction proceeded under visible light irradiation to afford a variety of 4-imidazolidinone derivatives under mild conditions in moderate to excellent yields. Secondary and tertiary C(sp3)-H bonds were aminated, and various functional groups were tolerated.

Synthesis of Tripeptide Derivatives with Three Stereogenic Centers and Chiral Recognition Probed by Tetraaza Macrocyclic Chiral Solvating Agents Derived from d -Phenylalanine and (1 S,2 S)-(+)-1,2-Diaminocyclohexane via 1H NMR Spectroscopy

Enantiomers of a series of tripeptide derivatives with three stereogenic centers (±)-G1-G9 have been prepared from d- and l-α-amino acids as guests for chiral recognition by 1H NMR spectroscopy. In the meantime, a family of tetraaza macrocyclic chiral solvating agents (TAMCSAs) 1a-1d has been synthesized from d-phenylalanine and (1S,2S)-(+)-1,2-diaminocyclohexane. Discrimination of enantiomers of (±)-G1-G9 was carried out in the presence of TAMCSAs 1a-1d by 1H NMR spectroscopy. The results indicate that enantiomers of (±)-G1-G9 can be effectively discriminated in the presence of TAMCSAs 1a-1d by 1H NMR signals of multiple protons exhibiting nonequivalent chemical shifts (ΔΔδ) up to 0.616 ppm. Furthermore, enantiomers of (±)-G1-G9 were easily assigned by comparing 1H NMR signals of the split corresponding protons with those attributed to a single enantiomer. Different optical purities (ee up to 90%) of G1 were clearly observed and calculated in the presence of TAMCSAs 1a-1d, respectively. Intermolecular hydrogen bonding interactions were demonstrated through theoretical calculations of enantiomers of (±)-G1 with TAMCSA 1a by means of the hybrid functional theory with the standard basis sets of 3-21G of the Gaussian 03 program.

Pd(ii)-Catalyzed aerobic 1,2-difunctionalization of conjugated dienes: Efficient synthesis of morpholines and 2-morpholones

A novel and efficient methodology concerning the Pd(ii)-catalyzed intermolecular difunctionalization of conjugated dienes is reported to synthesize a series of functionalized morpholines and 2-morpholones. Widely distributed and easily obtained β-amino alcohols and α-amino acids, as starting nitrogen and oxygen sources, are successfully applied in the difunctionalization of conjugated dienes respectively. The majority of the desired products were obtained in moderate to excellent yields. Oxygen was successfully employed as a terminal oxidant. Further transformation of the generated products allowed for the expansion of structural diversity.