52533-09-2

Upstream product

• 3424-93-9 4-methoxyphenylacetamide 
• 52533-08-1 N-p-Methoxyphenyltrichlormethansulfenamid 
• 2757-23-5 chloro(chlorosulfanyl)methanone 

Downstream Products

• 73501-03-8 5-(p-methoxyphenyl)-2,2-bis(trichloromethyl)-1,3,4-oxathiazole 
• 73501-04-9 5-(p-methoxyphenyl)-2-phenyl-2-trifluoromethyl-1,3,4-oxathiazole 
• 99315-70-5 3-(p-methoxyphenyl)-5-phenyl-1,2,4-thiadiazole 
• 76162-57-7 ethyl 3-(p-methoxyphenyl)isothiazole-4-carboxylate 
• 76162-58-8 ethyl 3-(p-methoxyphenyl)isothiazole-5-carboxylate 
• 874-90-8 4-methoxybenzonitrile 
• 51270-70-3 dimethyl 2,4-diacetyl-1,3-dithietane-2,4-dicarboxylate 
• 132283-38-6 methyl 2-(p-methoxyphenyl)-6-methyl-1,4,3-oxathiazine-5-carboxylate 
• 76342-95-5 tetramethyl 1,3-dithietane-2,2,4,4-tetracarboxylate 
• 111480-70-7 3-(4-methoxyphenyl)-5-(4-nitrophenylthio)-1,2,4-thiadiazole 
• 111480-71-8 3-(4-methoxyphenyl)-5-(1-naphthylthio)-1,2,4-thiadiazole 
• 111480-66-1 5-(2-chloro-4,6-dinitrophenylthio)-3-(4-methoxyphenyl)-1,2,4-thiadiazole 
• 71309-86-9 4-Methoxybenzonitrilsulfid 
• 10514-27-9 3-(p-methoxyphenyl)isothiazole 

Relevant academic research and scientific papers

Synthesis and biological evaluation of novel isothiazoloquinoline quinone analogues

Natural quinones and their analogues have attracted growing attention because of their novel anticancer activities. A series of novel isothiazoloquinoline quinone analogues were synthesized and evaluated for antitumor activities against four different kind of cancer cells. Among them, isothiazoloquinolinoquinones inhibited cancer cells proliferation effectively with IC50 values in the nanomolar range, and isothiazoloquinolinoquinone 13a induced the cell apoptosis. Further exploration of possible mechanism of action indicates that 13a not only activates ROS production through NQO1-directed redox cycling but also inhibits the phosphorylation of STAT3. These findings indicate that 13a has potential use for the development of new skeleton drug candidate as an efficient substrate of NQO1 and STAT3 inhibitor.

Discovery of an Isothiazole-Based Phenylpropanoic Acid GPR120 Agonist as a Development Candidate for Type 2 Diabetes

We have discovered a novel series of isothiazole-based phenylpropanoic acids as GPR120 agonists. Extensive structure-activity relationship studies led to the discovery of a potent GPR120 agonist 4x, which displayed good EC50 values in both calcium and β-arrestin assays. It also presented good pharmaceutical properties and a favorable PK profile. Moreover, it demonstrated in vivo antidiabetic activity in C57BL/6 DIO mice. Studies in WT and knockout DIO mice showed that it improved glucose handling during an OGTT via GPR120. Overall, 4x possessed promising antidiabetic effect and good safety profile to be a development candidate.

ANTIBACTERIAL AGENTS

Compounds of formula (IA) or (IB) have antibacterial activity: wherein W is =CH- or =N-; Ri and R2 are independently selected from hydrogen, fluoro and chloro, provided that Ri and R2 are not each hydrogen when W is =CH-; n is 0 or 1; X is -O-, -S-, or -C

Non-ATP competitive glycogen synthase kinase 3β (GSK-3β) inhibitors: Study of structural requirements for thiadiazolidinone derivatives

The 2,4-disubstituted thiadiazolidinones (TDZD) were described as the first non-ATP competitive GSK-3β inhibitors. New modifications in this heterocyclic ring are here reported to study the influence on the biological activity. The basic skeleton of 1,2,4-thiadiazole and also one of the carbonyl groups are kept, while different modifications are introduced in positions 3 and 5, respectively. The GSK-3β activity of the new thiadiazole derivatives here synthesized showed IC50 values for some of the compounds in the micromolar range. Additionally, ATP competition studies have been carried out, showing that as well as the first generation of TDZD, these new compounds act in a non-competitive manner. With this study, additional requirements for the biological activity of the TDZD family have been delineated.

Heteroarylnitrones as drugs for neurodegenerative diseases: Synthesis, neuroprotective properties, and free radical scavenger properties

New 1,2,4-thiadiazolylnitrones and furoxanylnitrones were developed and evaluated as neuroprotective agents on a human neuroblastoma (SH-SY5Y) cells model. They inhibited at low micromolar concentrations the oxidative damage and the death induced by exposure to hydrogen peroxide. These heteroarylnitrones showed excellent peroxyl free radical absorbance capacities, analyzed by oxygen radical absorbance capacity (ORAC) assay with fluorescein as the fluorescent probe, ranging from 1.5- to 16.5-fold the value of the reference nitrone, α-phenyl-N-tert-butylnitrone (PBN). The electron spin resonance spectroscopy (ESR) demonstrated the ability of these derivatives to directly trap and stabilize oxygen, carbon, and sulfur-centered free radicals. These results demonstrated the potential use of these heteroarylnitrones as neuroprotective agents in preventing the death of cells exposed to enhanced oxidative stress and damage.

Substituent effects on15N and13C NMR chemical shifts of 5-phenyl-1,3,4-oxathiazol-2-ones: A theoretical and spectroscopic study

The synthesis and assignment of 15N and 13C NMR signals of the 1,3,4-oxathiazol-2-one ring in a series of para-substituted 5-phenyl derivatives are reported. DFT calculations of 15N and 13C chemical shifts correspond closely to observed values. Substituent effects are interpreted in terms of the Hammett correlation and calculated bond orders. Copyright

Herbicidal [1,2,4] thiadiazoles

Novel herbicidal compounds of the general formula STR1 wherein A represents an optionally substituted alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, heteroaryl, aralkyl or heteroaralkyl group; R1 represents a hydrogen atom or an acyl group; an

Dithiazoles and Related Compounds. Part 3. Preparation of 5H-1,4,2-Dithiazoles via 1,3-Dipolar Cycloadditions between Nitrile Sulphides and Thiocarbonyl Compounds, and some Conversions into 3,5-Diaryl-1,4,2-dithiazolium Salts

Thermolysis of 1,3,4-oxathiazol-2-ones 3 in the presence of thiocarbonyl compounds gives modest to good yields of the little-known 5H-1,4,2-dithiazoles 1, the reaction being successful with diaryl, aryl alkyl and dialkyl ketones, and thiono esters, but failing with dithio esters and tertiary thioamides.The influence of substituents is discussed.Solvolysis of 5-ethoxy-5H-1,4,2-dithiazoles, derived from thiono esters, with perchloric acid in acetic anhydride gives high yields of 3,5-diaryl-1,4,2-dithiazolium salts 9.

IMINATION OF SULFUR-CONTAINING COMPOUNDS. XXIII. EFFECT OF THE ACIDIC CHARACTERISTICS OF N-SUBSTITUTED SULFENAMIDES ON THEIR ABILITY TO BE IMINATED BY THE SODIOCHLOROAMIDES OF SULFONIC ACIDS

The ability of N-substituted sulfenamides to be iminated by the sodiochloroamides of sulfonic acids is due primarily to their acidity and to the type of solvent employed.N-Substituted sulfonamides with pKa > 11.0 are imidated by the sodiochloroamides of sulfonic acids in acetone.The imination of N-substituted sulfenamides with pKa 8-11 must be carried out in strongly basic solvents with high dielectric constants (an aqueous alkaline medium, pyridine, etc.); sulfenamides with pKa 8 are iminated by the sodiochloroamides of sulfonic acids in the form of the sulfenamide anion.

Nitrile Sulphides. Part 1. 1,3-Dipolar Cycloaddition to Carbonyl Groups activated by Trihaloalkyl Substituents; Synthesis and Crystal Structure of 1,3,4-Oxathiazoles

Nitrile sulphides, generated by the thermal decarboxylation of 1,3,4-oxathiazol-2-ones, undergo 1,3-dipolar cycloaddition to the carbonyl group in chloral, hexachloroacetone and α,α,α-trifluoroacetophenone to yield 2,2,5-trisubstituted 1,3,4-oxathiazoles (18 - 76percent).Characterisation of the products is based on analytical and spectroscopic evidence, and is confirmed for 5-phenyl-2-trichloromethyl-1,3,4-oxathiazole and 5-(p-methoxyphenyl)-2-phenyl-2-trifluoromethyl-1,3,4-oxathiazole by X-ray crystal structure analyses.The oxathiazole rings are planar, with a localised C=N double bond.