7205-81-4

Upstream product

• 7205-60-9 1-(ethylsulfanyl)-4-nitrobenzene 
• 5324-47-0 sodium ethanesulfonate 
• 100-16-3 4-nitrophenylhydrazone 
• 1849-36-1 para-nitrobenzenethiol 
• 100-00-5 4-chlorobenzonitrile 
• 7205-70-1 (R,S)-1-(ethylsulfinyl)-4-nitrobenzene 
• 13113-79-6 sodium 4-nitrobenzenethiolate 
• 350-46-9 4-Fluoronitrobenzene 

Downstream Products

• 108079-03-4 5-nitro-5-(4'-ethylsulfonylphenyl)-1,3-dioxane 
• 6334-01-6 (4-Aminophenyl)-aethyl-sulfon 

Relevant academic research and scientific papers

Method for synthesizing sulfone compounds under photocatalysis condition

The invention belongs to the technical field of compound preparation, and particularly relates to a method for synthesizing sulfone compounds under a photocatalysis condition. Aromatic hydrazine and sulfinate are used as raw materials, and under the action of alkali and a solvent, a sulfone compound is generated through reaction under the condition of air or oxygen under the illumination of visible light. According to the method disclosed by the invention, aryl hydrazine is used as an arylation reagent, polyacid salt is used as a catalyst or an organic photosensitizer is used as a catalyst, and the sulfones compound can be efficiently synthesized by coupling with sulfinate under the condition of room temperature through visible light irradiation. The method has good substrate universalityand relatively mild reaction conditions, is not only a substitute for synthesizing sulfone compounds by coupling from simple substrates reported at present, but also broadens the new application of the polyacid salt in the field of photocatalysis.

3-PHOSPHOGLYCERATE DEHYDROGENASE INHIBITORS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same.

Asymmetric counteranion-directed iron catalysis: A highly enantioselective sulfoxidation

A highly active and enantioselective ion-pair sulfoxidation catalyst, consisting of an achiral iron(III)-salen cation and a chiral phosphate counteranion, mediates the oxidization of various sulfides with high yields and enantioselectivities. The enantioselectivities observed, especially for electron-poor substrates, represent the best results so far in manganese and iron-salen systems. This work represents the first application of our concept of asymmetric counteranion-directed catalysis (ACDC) to iron catalysis. Copyright

A kinetic investigation, supported by theoretical calculations, of steric and ring strain effects on the oxidation of sulfides and sulfoxides by dimethyldioxirane in acetone

The oxidations of alkyl 4-nitrophenyl, and dialkyl, sulfides and sulfoxides by dimethyldioxirane in acetone occur by concerted mechanisms but the sulfides respond differently from the sulfoxides to variation in the alkyl group. The reactions of the sulfides are inhibited by the steric effects of alkyl groups and these predominate over their inductive effects. By contrast, the reactions of these limited sets of sulfoxides are insensitive to alkyl steric effects but there is an indication of steric acceleration when a broader set of sulfoxides is considered. This behaviour is rationalised in terms of the differences in dipolar charge and its solvation between the ground state and transition state for the two types of substrate. The oxidations of cyclic sulfides and sulfoxides also exhibit contrasting behaviour. The reactivity of the sulfides is insensitive to ring strain but is explicable in frontier orbital terms whereas that of the sulfoxides is partly dependent upon the change in ring strain between reactant and product on oxidation, a difference rationalised in terms of the relative positions of the transition states in the reaction coordinates of the two oxidations. The reactivity of 4-, 5- and 6-membered cyclic sulfoxides is also dependent on a ring-size related property of the transition state. Calculations at the B3-LYP/6-31G* level of density functional theory on both ground states and transition states, including simulation of solvation by acetone, strongly support the mechanistic conclusions reached in this and earlier work.

1,2-Diarylpyrroles as potent and selective inhibitors of cyclooxygenase- 2

Series of 1,2-diarylpyrroles has been synthesized and found to contain very potent and selective inhibitors of the human cyclooxygenase-2 (COX-2) enzyme. The paper describes short and practical syntheses of the target molecules utilizing the Paal-Knorr reaction. Electrophilic substitution on 1 proceeds in a regioselective fashion, and the method was used to generate a number of tetrasubstituted pyrroles. Detailed SAR on the series has been studied by modifications of the aryl rings and the substituents in the pyrrole ring. Diarylpyrrole 1 is a very potent (COX-2, IC50 = 60 nm) and selective (COX-1/COX-2 = > 1700) inhibitor whereas the isomeric 2 is completely inactive against COX-2. Modifications of the substituents on the fluorophenyl ring in 1 yields very potent inhibitors of COX-2 (IC50 = 40- 80 nm) with excellent selectivity(1200 to >2500) vs COX-1, Analog 20 containing a sulfonamide group is an excellent inhibitor of COX-2 with an IC50 of 14 nm. Tetrasubstituted pyrroles containing groups such as COCF3, SO2CF3, or CH2OAr at position 3 in the pyrrole ring give excellent inhibitors (COX-2, IC50 = 30-120 nm). In vivo testing in the carrageenan- induced paw edema model in the rat establishes that the 1,2-diarylpyrroles are orally active antiinflammatory agents. Compound 3 is the most potent inhibitor of edema with an ED50 of 4.7 mpk.

Photooxidation of alkyl 4-nitrophenyl sulfides and sulfoxides. Observation of oxidative C-S bond cleavage and rearrangement reactions

Alkyl 4-nitrophenyl sulfides and sulfoxides undergo a self-photoinduced, singlet oxygen oxidation to produce a variety of products, including sulfonates and carbonyl compounds formed by the oxidative cleavage of the C-S bond of the sulfides and sulfoxides. Structural rearrangements are observed in the resulting carbonyl compounds formed in the oxidative cleavage of the C-S bond in the tert-amyl and 2-phenylethyl sulfides. An overall mechanism is proposed which involves the formation of peroxysulfoxides and peroxysulfones which undergo heterolytic C-S bond cleavage to form ion pairs which recombine to form persulfenates or persulfinates which then undergo photo- and/or thermallyinduced homolytic O-O bond cleavage to form alkoxy and sulfinyl or sulfonyl radicals. The alkoxy radicals undergo β-scission, disproportionation, or recombination with the sulfonyl radical to form the observed products. These C-S oxidative cleavage reactions have only been rarely observed in the earlier studies on the singlet oxygen oxidation studies of dialkyl sulfides, and are attributed, in part, to the presence of the 4-nitro group on the aromatic ring which greatly affects the susceptibility of the sulfur atom of the sulfides and sulfoxides toward nucleophilic attack, and on the reactivity of the peroxysulfoxides and peroxysulfones toward heterolytic cleavage of the O-S bond.