3406-75-5

Usage

Uses

Used in Pharmaceutical Industry:
2-[(4-NITROPHENYL)SULFANYL]ACETIC ACID is used as a precursor in the synthesis of pharmaceutical compounds for its ability to participate in various chemical reactions, contributing to the development of new medications.
Used in Organic Synthesis:
2-[(4-NITROPHENYL)SULFANYL]ACETIC ACID is used as a starting material for the synthesis of other organic compounds, enabling the creation of a diverse range of chemical products.
Used in Agrochemical Development:
2-[(4-NITROPHENYL)SULFANYL]ACETIC ACID is used as a building block in the development of new agrochemicals, potentially enhancing crop protection and yield through novel chemical formulations.

InChI:InChI=1/C8H7NO4S/c10-8(11)5-14-7-3-1-6(2-4-7)9(12)13/h1-4H,5H2,(H,10,11)

Upstream product

• 68-11-1 mercaptoacetic acid 
• 100-00-5 4-chlorobenzonitrile 
• 79-08-3 bromoacetic acid 
• 1849-36-1 para-nitrobenzenethiol 
• 97209-76-2 3-Hydroxy-3-(4-methoxy-phenyl)-2-(4-nitro-phenylsulfanyl)-propionic acid methyl ester 
• 900537-28-2 N-methyl-N-(4-methoxyphenyl)-4-nitrobenzene sulphonamide 
• 900537-29-3 N-methyl-N-nosyl-o-fluoroaniline 
• 900537-33-9 N-methyl-N-nosyl-m-aminobenzonitrile 
• 900537-30-6 N-(2-iodophenyl)-N-methyl-4-nitrobenzenesulfonamide 
• 900537-31-7 N-methyl-N-nosyl-p-nitroaniline 
• 881005-27-2 methyl N-methyl-N-nosyl-p-aminobenzoate 
• 900537-32-8 N-methyl-N-nosyl-p-aminoacetophenone 
• 64999-94-6 N-methyl-N-phenyl-4-nitrobenzene sulphonamide 
• 211676-01-6 N-methyl-N-nosyl-m-toluidine 

Downstream Products

• 100959-23-7 bromo-(4-nitro-phenylsulfanyl)-acetic acid 
• 102582-90-1 tris(2-hydroxyethyl)ammonium 4-nitrophenylsulfanylacetate 
• 67141-29-1 2-(p-nitrophenylthiaoxy)acetyl chloride 
• 105892-18-0 2-hydroxyethylammonium 4-nitrophenylsulfanylacetate 
• 105892-19-1 (4-Nitro-phenylsulfanyl)-acetic acid; compound with 2-(2-hydroxy-ethylamino)-ethanol 
• 1849-36-1 para-nitrobenzenethiol 
• 298-12-4 Glyoxilic acid 
• 51957-78-9 E-3-(4-nitrophenylthiomethylene)phthalide 
• 34279-35-1 3-[1-(4-Nitro-phenylsulfanyl)-meth-(Z)-ylidene]-3H-isobenzofuran-1-one 
• 104-18-7 2-(4-aminophenylthio)acetic acid 
• 14769-09-6 methyl 2-((4-nitrophenyl)sulfonyl)acetate 
• 724707-50-0 bromo-(4-nitro-benzenesulfonyl)-acetic acid methyl ester 
• 3406-71-1 (4-nitrophenylsulfinyl)acetic acid 
• 101032-21-7 5,5'-dimethoxy-N,N'-ethylenebis(salicylideneaminato) manganese(III)(hexafluorophosphate) 

Relevant academic research and scientific papers

Hydrogen-bonded molecular ladders in S-(4-nitrophenyl)thioglycolic acid

Hydrogen-bonded molecular ladders in S-(4-nitrophenyl)thioglycolic acid was studied. The supramolecular structure of S-(4-nitrophynl)thioglycolic acid, O2NC6H4S-CH2COOH where both C-H···O hydrogen bonds and arom

Structure-based modification of carbonyl-diphenylpyrimidines (Car-DPPYs) as a novel focal adhesion kinase (FAK) inhibitor against various stubborn cancer cells

A family of carbonyl-substituted diphenylpyrimidine derivatives (Car-DPPYs) with strong activity against focal adhesion kinase (FAK), were described in this manuscript. Among them, compounds 7a (IC50 = 5.17 nM) and 7f (IC50 = 2.58 nM) displayed equal anti-FAK enzymatic activity to the lead compound TAE226 (6.79 nM). In particular, compound 7a also exhibited strong antiproliferative activity against several stubborn cancer cells, including AsPC-1 cells (IC50 = 0.105 μM), BxPC-3 cells (IC50 = 0.090 μM), and MCF-7/ADR cells (IC50 = 0.59 μM). Additionally, compound 7a also showed great antitumor efficacy in vivo via aAsPC-1 cancer Xenograft mouse model. The preliminary mechanism study by Western blot analysis revealed that 7a repressed FAK phosphorylation in AsPC cancer cells. Taken together, the results indicate that compound 7a may serve as a promising preclinical candidate for treatment of stubborn cancers.

Thiopyrimidine heterocycle anti-tumor compounds as well as preparation method and application thereof

The invention relates to thiopyrimidine heterocycle anti-tumor compounds as well as a preparation method and an application thereof. The anti-tumor compounds specifically have the structure shown in aformula (I). The invention also relates to the compounds shown in the formula (I), pharmaceutically acceptable salts of the compounds or pharmaceutical composition containing the compounds. The pharmaceutical composition can treat tumor diseases by inhibiting wild type EGFR (epidermal growth factor receptor) and mutant type EGFR-T790M PTK (protein tyrosine kinase) and is particularly applied to treatment of small cell lung cancer, non-small cell lung cancer and EGFR-T790M mutant type non-small cell lung cancer.

Structural optimization of diphenylpyrimidine scaffold as potent and selective epidermal growth factor receptor inhibitors against L858R/T790M resistance mutation in nonsmall cell lung cancer

A new class of thiodiphenylpyrimidine analogs (Thio-DPPY) were synthesized as potent and selective EGFR T790M inhibitors to overcome gefitinib resistance in nonsmall cell lung cancer (NSCLC). This structural optimization led to the identification of two p

Synthesis of thioether andrographolide derivatives and their inhibitory effect against cancer cells

A series of novel thioether andrographolide derivatives were synthesized by incorporating various aromatic (or heteroaromatic) substituents into C-12 or 14-OH. A total of 38 andrographolide derivatives were prepared and evaluated for their in vitro inhibi

Electrophilic and nucleophilic pathways in ligand oxide mediated reactions of phenylsulfinylacetic acids with oxo(salen)chromium(V) complexes

The mechanism of oxidative decarboxylation of phenylsulfinylacetic acids (PSAA) by oxo(salen)Cr(V)+ ion in the presence of ligand oxides has been studied spectrophotometrically in acetonitrile medium. Addition of ligand oxides (LO) causes a red shift in the λmax values of oxo(salen) complexes and an increase in absorbance with the concentration of LO along with a clear isobestic point. The reaction shows first-order dependence on oxo(salen)-chromium(V)+ ion and fractional-order dependence on PSAA and ligand oxide. Michaelis-Menten kinetics without kinetic saturation was observed for the reaction. The order of reactivity among the ligand oxides is picoline N-oxide > pyridine N-oxide > triphenylphosphine oxide. The low catalytic activity of TPPO was rationalized. Both electron-withdrawing and electron-donating substituents in the phenyl ring of PSAA facilitate the reaction rate. The Hammett plots are non-linear upward type with negative ρ value for electron-donating substituents, (ρ- = -0.740 to -4.10) and positive ρ value for electron-withdrawing substituents (ρ+ = +0.057 to +0.886). Non-linear Hammett plot is explained by two possible mechanistic scenarios, electrophilic and nucleophilic attack of oxo(salen)chromium(V)+-LO adduct on PSAA as the substituent in PSAA is changed from electron-donating to electron-withdrawing. The linearity in the log k vs. Eox plot confirms single-electron transfer (SET) mechanism for PSAAs with electron-donating substituents.

Highly specific N-monomethylation of primary aromatic amines

A synthetic methodology for the specific conversion of primary aromatic amines into their N-monomethyl derivatives under very mild conditions is presented. Anilines are treated with 4-nitrobenzenesulfonyl (nosyl) chloride to generate the corresponding sulfonamides 2 in high yields. The subsequent N-methylation reaction of the sulfonamides 2 with a solution of diazomethane is rapid and quantitative. Removal of the nosyl protecting group is readily carried out using the reagent system mercaptoacetic acid/1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) affording the N-monomethylated aromatic amines 4. The procedure is convenient, efficient, and gives rise to the N-monomethyl-anilines exclusively.

Highly stereoselective asymmetric pummerer reactions that incorporate intermolecular and intramolecular nonbonded S...O interactions

New chiral sulfoxides (RS,S)-3, (SS,S)-3, (R S,S)-4, and (SS,S)-4 and known chiral sulfoxides (R S)-5, (RS)-6, and (RS)-7 were synthesized, and the stereochemistry of the new sulfoxides (RS,S)-3 and (R S,S)-4 was determined by X-ray crystallographic analysis. In their crystallographic structures, the intramolecular nonbonded S...O close contacts were recognized. Analyses of several sulfoxide complexes including rac-11 with N,N-dimethylacetamide (DMAC) or N-methyl-2-pyrrolidone (NMP) in a MeOH solution utilizing cold-spray ionization mass spectrometry provided, for the first time, direct information for intermolecular nonbonded S...O interactions between sulfoxides and amide (or lactam) in a solution. Highly diastereoselective and enantioselective Pummerer reactions based on the concept of intermolecular and intramolecular nonbonded S...O interactions were performed by treatment of several chiral sulfoxides (RS, S)-3, (SS, S)-3, (RS, S)-4, (SS, S)-4, (R S)-5, (RS)-6, and (RS)-7 with acetic anhydride and trimethylsilyl triflate (TMSOTf) in DMAC, NMP, N,N-dimethylformamide, and N-formylpiperidine. Mechanistic studies on these facile stereoselective Pummerer reactions revealed the necessity for the amide/TMSOTf complex, such as 26 or 27, to be an efficient activation reagent for Ac2O and a trapping reagent for the released acetate ion, and that DMAC and NMP had a positive effect on this highly stereoselective chiral transfer reaction.

(4-Nitrophenylsulfinyl)acetic acid, a three-dimensional hydrogen-bonded framework built from a combination of two-centre O-H...O and C-H...O hydrogen bonds and a three-centre C-H...(O)2 hydrogen bond

Molecules of the title compound, C8H7NO5S, are linked into sheets by a combination of two-centre hydrogen bonds, one of type O-H...O [H...O = 1.81 A, O...O = 2.648 (2) A and O-H...O = 173°] and three of type C-H...O [H...O