3405-88-7

Usage

InChI:InChI=1/C8H7ClO2S/c9-6-1-3-7(4-2-6)12-5-8(10)11/h1-4H,5H2,(H,10,11)/p-1

Upstream product

• 109-72-8 n-butyllithium 
• 60-29-7 diethyl ether 
• 123-09-1 4-chlorophenyl methyl sulfide 
• 79-08-3 bromoacetic acid 
• 106-54-7 p-Chlorothiophenol 
• 62499-16-5 (E)-1-((4-chlorophenyl)diazenyl)pyrrolidine 
• 68-11-1 mercaptoacetic acid 
• 106-47-8 4-chloro-aniline 
• 52377-68-1 ethyl 2-(p-chlorophenylthio)acetate 
• 64-69-7 Iodoacetic acid 
• 103-04-8 (phenylthio)acetic acid 
• 3926-62-3 sodium monochloroacetic acid 
• 18803-44-6 sodium p-chlorothiophenolate 
• 79-11-8 chloroacetic acid 

Downstream Products

• 3405-89-8 2-(4-chloro-phenylsulfonyl)acetic acid 
• 3996-47-2 4-Chlorophenylsulfenylacetic acid 
• 35859-16-6 (4-chloro-phenylsulfanyl)-acetic acid 2-morpholin-4-yl-ethyl ester 
• 16503-68-7 2,2-dichloro-2-(p-chlorophenylthio)acetyl chloride 
• 3341-23-9 N-β-(3,4-Dimethoxy-phenyl)-aethyl-p-chlor-phenyl-mercapto-acetamid 
• 105892-13-5 (4-Chloro-phenylsulfanyl)-acetic acid; compound with 2-oxazolidin-3-yl-ethanol 
• 15446-15-8 methyl 2-[(4-chlorophenyl)thio]acetate 
• 87298-93-9 2-(1-Oxa-4-aza-spiro[4.5]dec-4-yl)-ethanol; compound with (4-chloro-phenylsulfanyl)-acetic acid 
• 105892-09-9 (4-Chloro-phenylsulfanyl)-acetic acid; compound with 2-dimethylamino-ethanol 
• 123-09-1 4-chlorophenyl methyl sulfide 
• 7031-25-6 2-(4'-chlorophenylmercapto)acetyl chloride 
• 158575-46-3 (R)-5-(α-p-chlorophenylthio)acetoxy-1,1-dimethoxyhexane 
• 158575-53-2 (S)-5-(α-p-chlorophenylthio)acetoxy-1,1-dimethoxyhexane 
• 1142-19-4 4,4'-dichlorodiphenyl disulfide 

Relevant academic research and scientific papers

A highly stereoselective oxidation and an easy one pot elimination methodology for 3-allyl-3-phenylthio-β-lactams

A novel, facile, highly efficient and stereoselective protocol for the synthesis of cis-3-allyl-3-phenylsulfinyl-β-lactams and 3-allylidene-β-lactams from cis-3-allyl-3-phenylthio-β-lactams using Selectfluor both as an oxidizing agent and as an eliminating agent with temperature as a control parameter over the reaction outcome has been reported. The methodology is able to conquer the earlier reported shortcomings of long reaction time (24–90 hrs.) and lack of control over product ratio. The synthesized compounds will serve as important synthons for compounds of enhanced biological activity and potency.

RETRACTED ARTICLE: Design, synthesis, and biological evaluation of heterotetracyclic quinolinone derivatives as anticancer agents targeting topoisomerases

A series of thiochromeno[2,3-c]quinolin-12-one derivatives with various substitutions were synthesized and evaluated as topoisomerase (Topo) inhibitors. Six (8, 10, 12, 14, 19, and 26) of 23 compounds showed strong inhibitory activities against Topo-media

Competitive behavior of nitrogen based axial ligands in the oxovanadium(IV)-salen catalyzed sulfoxidation of phenylmercaptoacetic acid

The sulfoxidation of twelve phenylmercaptoacetic acids (PMAA) by H2O2 catalyzed by three oxovanadium(IV)-salen complexes, having varied substituents on PMAA and salen with regard to their position, size and inductive effect, has been performed spectrophotometrically in 100percent acetonitrile medium. Three nitrogen bases (NB), pyridine (Py), imidazole (ImH) and 1-methylimidazole (MeIm), were used as axial ligands. It has been found that the rate of sulfoxidation is not only tuned by the substituents on PMAA and salen, but it is also varied by the addition of nitrogen bases. The observed order of retardation found among the different nitrogen bases is ImH > MeIm > Py. The rate of reaction decreases with the increase in concentration of the NB axial ligands. The strongly binding ImH shows the least reactivity. Hydroperoxovanadium(V)-salen has been proposed as the sole active oxidizing species. A detailed mechanistic study reveals that the low rate constant values in the presence of the nitrogen base is due to the existence of competition of NB with H2O2 and PMAA during the formation of active species and the coordination of PMAA with active species, respectively. Both electron donating and electron withdrawing substituents on PMAA retard the sulfoxidation rate significantly. The Hammett correlation between the rate constants and substituent constants shows a non-linear concave downward curve which is explained by the existence of two different rate determining steps within the same mechanism; coordination of PMAA with the active species for electron withdrawing substituents and transfer of oxygen to PMAA for electron donating substituents. All the experimental observations are explained by proposing a suitable mechanism.

Studies towards synthesis and Lewis acid catalysed functionalization of 3-(4′-substitutedphenylthio)-azetidin-2-ones

Abstract: Medicinal chemistry of heterocycles especially β-lactams have been an important discovery in today’s mankind. β-Lactam nucleus is structural feature and core of the biological activity of one of most successful classes of therapeutics to date ch

The synthesis and characterization of tetramic acid derivatives as Mdm2-p53 inhibitors

We present syntheses, prediction of tautomer forms and activities of the second generation of the Mdm2-p53 inhibitors that are based on the tetramic acid scaffold. The inhibitors do not contain 6-chloroindole. Binding of these compounds to Mdm2 was checked by two orthogonal methods: the fluorescence polarization and the 1H-15N HSQC NMR titration experiments. We discovered that the 3-phenylthio-substituted tetramic acid derivatives exist in solution solely in their enol forms which is in contrast to the similar 3-aliphatic substituted derivatives. The inhibitory (Ki) and dissociation (KD) constants are in low micromolar ranges with the best binding compound 9a having KD = 2.9 μM. Furthermore, our data show that the compounds indeed bind to the p53-binding pocket of Mdm2 and do not cause dimerization of Mdm2. The current work provides solid base for further rational design of the Mdm2/p53 inhibitors.

FMS-LIKE TYROSINE KINASE INHIBITORS

Provided are compounds of formula (I-1) -(I-4),which can be used as FLT3 inhibitors and for treatment and/or prevention of tumors.

FMS-LIKE TYROSINE KINASE INHIBITORS

The present invention relates to Fms-like tyrosine kinase (FLT3) inhibitors. The present invention provides novel 4-quinolinone derivatives used as FLT3 inhibitors and for treatment and/or prevention of tumors.

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.

Importance of ground state stabilization in the oxovanadium(IV)-salophen mediated reactions of phenylsulfinylacetic acids by hydrogen peroxide – Non-linear Hammett correlation

A systematic study on the oxidative decarboxylation of a series of phenylsulfinylacetic acids (PSAA) by hydrogen peroxide with four oxovanadium(IV)-salophen catalysts in 100% acetonitrile medium is presented. The hydroperoxovanadium(V)-salophen generated from the reaction mixture is identified as the bonafide active oxidizing species. Introduction of electron donating groups (EDG) in the oxovanadium(IV)-salophen catalyst and electron withdrawing groups (EWG) in PSAA enhances the reactivity, whereas EWG in the catalyst and EDG in PSAA have a retarding effect on the reaction. A Hammett correlation displays a non-linear downward curvature, which consists of two intersecting straight lines and the ρ value shifts from small positive to moderately high as the substituents change from EWG to EDG. The importance of the ground state stabilization of PSAA is inferred from a linear Yukawa–Tsuno plot. Based on the observed substituent effects and the spectral changes, a mechanism involving electrophilic attack of PSAA on the nucleophilic peroxo oxygen atom of the vanadium complex in the rate determining step followed by oxygen atom transfer is proposed.

Modulation of catalytic activity by ligand oxides in the sulfoxidation of phenylmercaptoacetic acids by oxo(salen)chromium(V) complexes

Mechanism of sulfoxidation of eleven para-substituted phenyl mercaptoacetic acids (PMAAs) by three oxo(salen)chromium(V)+PF6?complexes in the presence of different ligand oxides (LOs) such as triphenylphosphine oxide, pyridine N-oxide and 4-picoline N-oxide have been studied spectrophotometrically in 100% acetonitrile medium. Spectral and kinetic profiles establish the formation of adduct, O[dbnd]Cr(V)(salen)+-LO as the reactive intermediate in the catalytic cycle. The rate of sulfoxidation is found to be enhanced significantly by the addition of LOs and introduction of substituent in PMAA and salen complex. Both electron releasing and electron withdrawing substituents in the substrate and oxidant facilitate the rate of sulfoxidation. Correlation with Hammett constants yields a non-linear concave upward curve. Based on the experimental results and substituent effects two different mechanisms, a direct oxygen atom transfer (DOT) for PMAAs with electron withdrawing substituents and a single electron transfer for PMAAs with electron donating substituents have been postulated.