6126-10-9

Usage

Uses

Used in Pharmaceutical Research and Organic Synthesis:
1-Tosylpyrazole is used as a building block for the development of novel drug molecules and bioactive compounds. Its reactivity and versatility make it an important reagent in the synthesis of various pharmaceuticals and agrochemicals, as well as in the preparation of heterocyclic compounds.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 1-Tosylpyrazole is used as a key component in the design and synthesis of new drug candidates. Its unique properties allow for the exploration of its potential in treating various diseases and conditions.
Used in Anti-Inflammatory and Anti-Cancer Research:
1-Tosylpyrazole has been studied for its potential anti-inflammatory and anti-cancer properties, making it a valuable target for further research and development. Its application in these areas could lead to the discovery of new therapeutic agents for the treatment of inflammation and cancer.

InChI:InChI=1/C10H10N2O2S/c1-9-3-5-10(6-4-9)15(13,14)12-8-2-7-11-12/h2-8H,1H3

Upstream product

• 288-13-1 NH-pyrazole 
• 1153-45-3 4-nitrophenyl 4-methylbenzenesulfonate 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 98-59-9 p-toluenesulfonyl chloride 
• 116228-41-2 4-bromo-1H-pyrazol-1-yl(4-methylphenyl)sulfone 
• 824-79-3 sodium 4-methylbenzenesulfinate 

Downstream Products

• 861161-55-9 2-ethyl-1-{1-[(4-methylphenyl)sulfonyl]-1H-pyrazol-5-yl}butan-1-ol 
• 142169-20-8 5-iodo-1-[(4-methylphenyl) sulfonyl]-1H-pyrazole 

Relevant academic research and scientific papers

Nickel-Catalyzed Cross-Electrophile Coupling with Organic Reductants in Non-Amide Solvents

Cross-electrophile coupling of aryl halides with alkyl halides has thus far been primarily conducted with stoichiometric metallic reductants in amide solvents. This report demonstrates that the use of tetrakis(dimethylamino)ethylene (TDAE) as an organic reductant enables the use of non-amide solvents, such as acetonitrile or propylene oxide, for the coupling of benzyl chlorides and alkyl iodides with aryl halides. Furthermore, these conditions work for several electron-poor heterocycles that are easily reduced by manganese. Finally, we demonstrate that TDAE addition can be used as a control element to ‘hold’ a reaction without diminishing yield or catalyst activity.

Iodine-catalyzed expeditious synthesis of sulfonamides from sulfonyl hydrazides and amines

A new synthesis of sulfonamides has been developed via an iodine-catalyzed sulfonylation of amines with arylsulfonyl hydrazides. This metal-free strategy employs readily accessible and easy to handle starting materials, catalysts and oxidants, and can be easily conducted under mild conditions, providing a convenient access to a wide range of sulfonamides in moderate to excellent yields within a short reaction time.

Iodine-catalyzed oxidative amination of sodium sulfinates: A convenient approach to the synthesis of sulfonamides under mild conditions

The iodine-catalyzed oxidative amination of sodium sulfinates in the presence of sodium percarbonate as the oxidant has been developed. The reaction shows good substrate scope and tolerates a wide range of functionalities in both amine and sodium sulfinate substrates. Aliphatic amines, heteroaromatic amines and hydrochloride salts of amines canbe employed as the amine sources in this transformation. Mechanistic studies indicated that a radical pathway might be involved in the reaction process. This transition-metalfree protocol offers an alternative and convenient approach for a preparation of a series of sulfonamides in moderate to good yields under mild conditions.

Selective palladium-catalyzed direct C-H arylation of unsubstituted N-protected pyrazoles

A highly selective C-5 arylation of N-dimethylaminosulfamoyl-protected pyrazole with aryl bromides is catalyzed by 2-5 mol% palladium in the presence of triphenylphosphine ligand and carboxylic acid additive. Selectivities up to 45:1 (C-5:C-4) can be achieved by running the reaction in non-polar solvents. A thorough study of scope and limitations shows good general tolerance of aryl bromide substitution. However, limitations on tolerance of ortho-subsitution and protic functional groups were established. Together with a telescoped deprotection step this method presents a viable alternative for the synthesis of C-3 arylated pyrazole building blocks.

Synthesis and structure-activity relationship of a novel series of heterocyclic sulfonamide γ-secretase inhibitors

γ-Secretase inhibitors have been shown to reduce the production of β-amyloid, a component of the plaques that are found in brains of patients with Alzheimer's disease. A novel series of heterocyclic sulfonamide γ-secretase inhibitors that reduce β-amyloid levels in cells is reported. Several examples of compounds within this series demonstrate a higher propensity to inhibit the processing of amyloid precursor protein compared to Notch, an alternative γ-secretase substrate.

QUINAZOLINE DERIVATIVES FOR USE IN THE TREATMENT OF CANCER

The invention concerns quinazoline derivatives of Formula (I) wherein each of Z, m, R1, n, R3,Z2 and R14 have any of the meanings defined hereinbefore in the description; processes for their preparation, pharmaceutical compositions containing them and their use in the manufacture of a medicament for use as an anti-invasive or anti-proliferative agent in the containment and/or treatment of solid tumour disease.

Pharmaceutical use of N-Carbamoylazole derivatives

The present invention relates to use of 1-carbamoylazole derivatives as medicaments and pharmaceutical compositions containing 1-carbamoylazole derivatives as the active ingredient, based on their DPPIV inhibiting effects. The present invention provides a dipeptidyl peptidase IV inhibiting agent comprising a compound represented by the general formula (I):

Nucleophilic substitution at a four-coordinate sulfur atom. IV. Reactivity of anionic nitrogen-containing nucleopiles

The second-order rate constants for reactions of anions derived from azoles, arenesulfonamides, and arenesulfonohydrazides with aryl toluenesulfonates and methyl iodide in 5% aqueous ethanol (μ 1.0) at 25°C were compared with corresponding rate constants for aliphatic and heterocyclic amines. The kinetic behavior of neutral and anionic nitrogen-containing bases in reactions involving acyl (4-nitrophenyl acetate and 4-nitrophenyl heptanoate) and toluenesulfonyl group transfer suggests that deviation from the Bronsted dependence is due to unfavorable solvation effects for nucleophiles with pKa ≥ 11.0 rather than to change in the transition state structure. In reactions with a soft substrate, methyl iodide, solvation effects scarcely play the determining role, and the reduced reactivity of the anionic nucleophiles relative to neutral species is most likely to result from structural differences in the transition states corresponding to methyl group transfer to neutral and anionic nitrogen-containing compounds. The α-effect with arenesulfonohydrazides was revealed for the first time. 1996 MAEe Cyrillic signΚ Hayκa/Interperiodica Publishing.