25688-17-9

Usage

Uses

Used in Pharmaceutical Industry:
1-(2-Nitrophenyl)-1H-pyrazole is used as a chemical intermediate for the synthesis of pharmaceutical compounds, leveraging its unique structure to contribute to the development of new drugs with potential therapeutic benefits.
Used in Agrochemical Industry:
In the agrochemical sector, 1-(2-Nitrophenyl)-1H-pyrazole is utilized as a precursor in the creation of agrochemicals, potentially enhancing crop protection and management through its incorporation into novel pesticides or other related products.
Used in Organic Synthesis:
1-(2-Nitrophenyl)-1H-pyrazole serves as a key building block in organic synthesis, facilitating the construction of complex organic molecules for a range of applications, including but not limited to materials science, medicinal chemistry, and specialty chemicals.
Used in Research and Development:
1-(2-Nitrophenyl)-1H-pyrazole is employed in research and development settings to investigate its pharmacological properties, with the aim of uncovering new uses and understanding its interaction with biological systems, which could lead to the discovery of new therapeutic agents or applications.

Upstream product

• 122-31-6 malondialdehyde bis(diethyl acetal) 
• 6293-87-4 o-nitrophenylhydrazine hydrochloride 
• 288-13-1 NH-pyrazole 
• 1493-27-2 ortho-nitrofluorobenzene 
• 102-52-3 malonaldehydebis(dimethylacetal) 
• 3034-19-3 (2-nitrophenyl)hydrazine 
• 29334-65-4 3,5-dimethyl-1-(2-nitrophenyl)-1H-pyrazole 
• 528-29-0 1,2-Dinitrobenzene 
• 577-19-5 2-nitrophenyl bromide 
• 100-00-5 4-chlorobenzonitrile 
• 88-73-3 2-Chloronitrobenzene 
• 609-73-4 o-nitroiodobenzene 
• 1126-00-7 1-phenylpyrazole 
• 99867-03-5 1-(2-nitro-phenyl)-1H-pyrazole-3,5-dicarboxylic acid 

Downstream Products

• 62569-41-9 4-nitro-1-(2-nitro-phenyl)-1H-pyrazole 
• 1964-92-7 2,2'-bis(pyrazol-1''-yl)azoxybenzene 
• 54705-91-8 2-(1H-pyrazol-1-yl)aniline 
• 25775-03-5 2-(1H-pyrazol-1-yl)-benzonitrile 
• 15728-92-4 1-(2,4-dinitro-phenyl)-4-nitro-1H-pyrazole 

Relevant academic research and scientific papers

Palladium-Catalyzed Direct C(sp2)-H ortho-Arylation of Anilides Using 2-Aminophenylpyrazole as the Directing Group

Palladium-catalyzed ortho-arylation of anilides was achieved using 2-aminophenyl-1H-pyrazole (2-APP) as a new directing group. Using Pd(OAc)2 as the catalyst and AgO as the promoter, mono- and diarylation of anilides were realized in up to 89% isolated yield. Further manipulation of the arylation product may be accomplished by a 2-step sequence involving an acidic hydrolysis of the methylated amide. More interestingly, in the presence of K2CO3, tandem C-C/C-N cyclization products were obtained for a couple of substrates.

An original class of small sized molecules as versatile fluorescent probes for cellular imaging

An unusual class, compact in size, of fluorescent probes based on pyridazino-1,3a,6a-triazapentalene scaffolds exhibits promising fluorescent properties (quantum yield values up to 73%, large Stokes shifts, emission wavelengths located in the green-yellow

A post-synthetically modified metal-organic framework for copper catalyzed denitrative C-N coupling of nitroarenes under heterogeneous conditions

Here we report, for the first time, the Ullmann C-N coupling reaction of nitroarenes which is achieved by using a copper containing metal-organic framework (MOF) catalyst under heterogenous conditions. The ready availability of nitroarenes and their low cost have made them ideal replacements for haloarenes as electrophilic coupling partners. Notably, the reaction protocol suppresses the by-product formation in the catalytic reaction. The catalyst has been designed and synthesized by two step post-synthesis functionalization of a MOF,viz.dabco MOF-1 with a -NH2functional group (DMOF-NH2). In the post-synthetic treatment, salicylaldehyde has been used for organic modification first and then copper(ii) was successfully incorporated onto the inner surface of the porous material. The hybrid porous solid thus obtained has been employed in the catalytic C-N coupling reaction of nitroarenes with a wide variety of amines under heterogeneous conditions, which displayed very high turnover frequencies (TOF) in catalytic reactions attesting its efficacy towards theN-arylation reaction.

Discovery of novel 2,4-diarylaminopyrimidine derivatives as potent and selective epidermal growth factor receptor (EGFR) inhibitors against L858R/T790M resistance mutation

A series of novel 2,4-diarylaminopyrimidine derivatives of AZD9291 were discovered as L858R/T790M mutant selective epidermal growth factor receptor (EGFR) inhibitors. The majority of these compounds exhibited moderate to excellent EGFR T790 M/L858R inhibitory activities and comparable anti-proliferative activities against double mutant over-expressed NCI-H1975 cells to that of AZD9291. The most promising compounds 8a displayed an IC50 of 4.1 nM against EGFR L858R/T790M mutants. 8a also showed excellent cytotoxic effect against NCI-H1975 cells with an IC50 of 59 nM and 100-fold selectivity over wide-type EGFR over-expressed A431 cells. Compound 8a significantly inhibited tumor growth in NCI-H1975 xenograft models at a non-toxic dose. Docking study performed for 8a with ATP binding site of EGFR-TK showed the similar binding mode to that of AZD9291. All these results suggested that compound 8a was a potential mutant-selective EGFR inhibitor.

Pyrimidine compounds

The present invention belongs to the field of pharmaceutical synthesis, and relates to pyrimidine compounds, a preparation method and applications thereof, a pharmaceutical composition containing the pyrimidine compounds as active components, and applications of the pyrimidine compounds in preparation of antitumor drugs. The present invention discloses a pyrimidine compound having a structure represented by a formula I, wherein W is NH, R1 is a nitrogen-containing five-membered heterocyclic ring, and R2 is a nitrogen-containing basic group. According to the present invention, the pyrimidine compound can inhibit a variety of tumor cells, can particularly and selectively act on EGFRL858R/T790M lung cancer cells, and can overcome the existing EGFR inhibitors, wherein the IC50 of the compounds is increased by 10-100 times compared to wild-type cells. The formula I is defined in the specification.

2-Aminophenyl-1H-pyrazole as a Removable Directing Group for Copper-Mediated C-H Amidation and Sulfonamidation

2-Aminophenyl-1H-pyrazole was discovered as a removable bidentate directing group for copper-mediated aerobic oxidative C(sp2-H) bond amidation and sulfonamidation. When Cu(OAc)2 was employed as the copper source and 1,1,3,3-tetramet

N-Picolinamides as ligands for Ullmann-type C-N coupling reactions

The use of N-phenyl-2-pyridincarboxamide-1-oxide as a ligand with Cu2O in Ullmann type C-N bond formations between aryl halides and N-heteroaryls in common solvents, such as MeCN, DMF, and DMSO at 82-120 °C has been successfully demonstrated. The ligand is effective when only 4% equiv is used relative to the substrate. The reaction provided the corresponding products in coupling of electron-rich, electron poor, and ortho-substituted aryl halides, including ortho aryl-chlorides, in good to very good yields. N-arylation is selectively preferred at the benzyl position when ortho-halide benzyl bromide is reacted with one equivalent of pyrazole. However, di-N-arylation is achieved in very high yields when 2.5 equiv of pyrazole is used, providing a stoichiometric control over the coupling reaction.

Aerobic oxidation of PdII to PdIV by active radical reactants: Direct C-H nitration and acylation of arenes via oxygenation process with molecular oxygen

A Pd-catalyzed aerobic oxidative C-H nitration and acylation of arenes with simple and readily available tert-butyl nitrite (TBN) and toluene as the radical precursors has been developed. Molecular oxygen is employed as the terminal oxidant and oxygen source to initiate the active radical reactants. Many different directing groups such as pyridine, pyrimidine, pyrazole, pyridol, pyridylketone, oxime, and azo groups can be employed in these novel transformations. The PdII/PdIV catalytic cycle through a radical process is the most likely pathway for these oxidative C-H nitration and acylation reactions.

Synthesis, antifungal activity and structure-activity relationships of novel 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid amides

A series of novel 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid amides were synthesized and their activities were tested against seven phytopathogenic fungi by an in vitro mycelia growth inhibition assay. Most of them displayed moderate to excellent activities. Among them N-(2-(5-bromo-1H-indazol-1-yl)phenyl)-3-(difluoro-methyl)-1-methyl-1H-pyrazole-4-carboxamide (9m) exhibited higher antifungal activity against the seven phytopathogenic fungi than boscalid. Topomer CoMFA was employed to develop a three-dimensional quantitative structure-activity relationship model for the compounds. In molecular docking, the carbonyl oxygen atom of 9m could form hydrogen bonds towards the hydroxyl of TYR58 and TRP173 on SDH.

Aromatic N-arylations catalyzed by copper-anchored porous zinc-based metal-organic framework under heterogeneous conditions

A highly porous Zn-based metal-organic framework (MOF) IRMOF-3 was covalently decorated with pyridine-2-aldehyde. The free amine group of IRMOF-3 upon condensation with pyridine-2-aldehyde affords a bidentate Schiff-base moiety in the porous matrix. The Schiff base moieties are availed to anchor copper(II) ions to display the catalyst's utility towards catalytic reactions. The catalyst was characterized by UV/Vis and IR spectroscopy, powder XRD spectrometry, SEM energy-dispersive X-ray spectrometry, and nitrogen sorption measurements. The catalyst exhibits excellent activity in catalyzing the N-arylation reaction of nitrogen-containing heterocycles with aryl bromides in DMSO medium, under mild condition (90°C) in the presence of Cs 2CO3. The porous catalyst demonstrates size selectivity towards substrate as a result of the presence of active sites inside the pores of the MOF. The anchored complex seems to be not leached or decomposed during the catalytic reactions up to five successive catalytic cycles, demonstrating practical advantages over homogeneous catalysis.