5334-39-4

Usage

Uses

Used in Pharmaceutical Industry:
3-Methyl-4-nitropyrazole is used as a reactant for the preparation of aminopyrazole derivatives, which are potent, selective, and brain-penetrant small molecule inhibitors of Leucine-rich repeat kinase 2 (LRRK2). These inhibitors play a crucial role in the development of therapeutic agents for the treatment of neurodegenerative disorders, such as Parkinson's disease, by targeting the LRRK2 enzyme and modulating its activity.

InChI:InChI=1/C4H5N3O2/c1-3-4(7(8)9)2-5-6-3/h2H,1H3,(H,5,6)

Upstream product

• 13808-64-5 4-bromo-3-methyl-1H-pyrazole 
• 1453-58-3 3-Methylpyrazole 
• 21901-41-7 4-methyl-5-nitropyridin-2(1H)-one 
• 15802-75-2 4-iodo-3-methyl-1H-pyrazole 

Downstream Products

• 3920-38-5 1,3-dimethyl-4-nitro-1H-pyrazole 
• 3920-42-1 1,5-dimethyl-4-nitro-1H-pyrazole 
• 113140-10-6 3-methyl-1H-pyrazole-4-amine 
• 5334-40-7 4-nitro-1H-pyrazole-5-carboxylic acid 
• 444010-36-0 1-(1-adamantyl)-3-methyl-4-nitropyrazole 
• 847139-22-4 tert-butyl 3-methyl-4-nitro-1H-pyrazole-1-carboxylate 
• 1201935-90-1 ethyl 2-(3-methyl-4-nitropyrazol-1-yl)acetate 
• 1374829-38-5 3-methyl-1-(4-(methylsulfonyl)phenyl)-4-nitro-1H-pyrazole 
• 1374830-18-8 5-methyl-1-(4-(methylsulfonyl)phenyl)-4-nitro-1H-pyrazole 
• 1374829-39-6 3-methyl-1-(4-(methylsulfonyl)phenyl)-4-amino-1H-pyrazole 
• 1374830-19-9 5-methyl-1-(4-(methylsulfonyl)phenyl)-4-amino-1H-pyrazole 
• 1006955-98-1 (3-methyl-4-nitro-1H-pyrazol-1-yl)acetonitrile 
• 1566543-93-8 C₉H₁₃N₃O₄ 
• 64517-88-0 1,3-dimethyl-1H-pyrazol-4-amine 

Relevant academic research and scientific papers

Structure of 3(5)-Methyl-4-nitropyrazole in the Solid State: Tautomerism, Crystallography and the Problem of Desmotropy

The first example of desmotropy in azoles has been found concerning 3-methyl-4-nitropyrazole and its tautomer, 5-methyl-4-nitropyrazole: the crystal and molecular structure of both tautomers has been determined by X-ray analysis, 13C CPMAS NMR spectroscopy has been used for studying the isomerization processes in the solid state.

Depsipeptides Featuring a Neutral P1 Are Potent Inhibitors of Kallikrein-Related Peptidase 6 with On-Target Cellular Activity

Kallikrein-related peptidase 6 (KLK6) is a secreted serine protease that belongs to the family of tissue kallikreins (KLKs). Many KLKs are investigated as potential biomarkers for cancer as well as therapeutic drug targets for a number of pathologies. KLK6, in particular, has been implicated in neurodegenerative diseases and cancer, but target validation has been hampered by a lack of selective inhibitors. This work introduces a class of depsipeptidic KLK6 inhibitors, discovered via high-throughput screening, which were found to function as substrate mimics that transiently acylate the catalytic serine of KLK6. Detailed structure-activity relationship studies, aided by in silico modeling, uncovered strict structural requirements for potency, stability, and acyl-enzyme complex half-life. An optimized scaffold, DKFZ-251, demonstrated good selectivity for KLK6 compared to other KLKs, and on-target activity in a cellular assay. Moreover, DKFZ-633, an inhibitor-derived activity-based probe, could be used to pull down active endogenous KLK6.

Chiral phosphoric acid-catalyzed enantioselective three- component aza-diels-alder reactions of aminopyrroles and aminopyrazoles

A highly stereoselective three-component Povarov reaction, catalyzed by (R)- and (S)-BINOL hydrogen phosphate, was achieved for the first time with aminopyrroles and aminopyrazoles as 2-azadiene precursors. A variety of aldehydes, enecarbamates, amino-substituted azines participated in the reaction to afford the tetrahydropyrrolopyridines and tetrahydropyrazolopyridines in good yields with excellent diatereo- and enantioselectivities. A stereochemical model is proposed to account for the observed absolute stereochemistry.

Faujasite catalyzed nitrodeiodination of iodopyrazoles

Nitrodeiodination of iodopyrazoles using nitric acid/Faujasite has been investigated. The present procedure is simple, rapid and convenient and requires no sulfuric acid or oleum and may be applied for the synthesis of several nitropyrazoles in good yield

A simple and environmentally benign nitration of pyrazoles by impregnated bismuth nitrate

We report herein a facile, rapid, and environmentally friendly synthesis of nitropyrazoles in good yields using silica-bismuth nitrate and silica-sulfuric acid-bismuth nitrate at room temperature for the first time. The relatively non-toxic nature, ease o

Silica-sulfuric acid catalyzed nitrodeiodination of iodopyrazoles

We report here the synthesis of nitropyrazoles in good to excellent yields from iodopyrazoles over silica-sulfuric acid catalyst for the first time. The present procedure require less acid, offers a simplified workup procedure, and may be applied for the

Facile and environmentally friendly synthesis of nitropyrazoles using montmorillonite K-10 impregnated with bismuth nitrate

Nitropyrazoles in higher yields were synthesized using montmorillonite K-10 impregnated with bismuth nitrate and the present procedure may be applied for the nitration of a wide variety of azoles in the drug and pharmaceutical industries.

HETEROCYCLYL PYRAZOLOPYRIMIDINE ANALOGUES AS JAK INHIBITORS

The present invention relates to compounds of formula (I) wherein X1 to X5, Y, Z1 to Z3, and R have the meaning as cited in the description and the claims. Said compounds are useful as JAK inhibitors for the treatment or prophylaxis of immunological, inflammatory, autoimmune, allergic disorders, and immunologically-mediated diseases. The invention also relates to pharmaceutical compositions including said compounds, the preparation of such compounds as well as the use as medicaments.

Facile, fast and safe process development of nitration and bromination reactions using continuous flow reactors

Chemists working in a pilot plant often face safety issues during scale-up operations. With the help of emerging microfluidic applications and microdevices, running hazardous, highly exothermic or potentially unstable reactions can be easily transposed into a safe continuous flow mode. This paper describes how a potentially hazardous pyrazole nitration and the bromination of a variety of electron-rich heteroaromatic substrates were efficiently performed using a cheap and easily available system for bench chemists. Advantages of the continuous flow mode in organic synthetic chemistry will be exemplified by the large-scale production of raw materials under safe, green and reproducible conditions.

Cyclizations of monocyclic 5-nitropyridin-2(1H)-ones

Reactions of 5-nitropyridin-2(1H)-one and its N-methyl derivative with hydrazine hydrate led to the formation of (1H-pyrazol-3-yl) acetohydrazide. Under analogous conditions, 1,3-dimethyl-5-nitropyridin2(1H)-one gave rise to 2-(1H-pyrazol-3-yl)propionohyd