59843-77-5

Usage

Uses

Used in Pharmaceutical Industry:
3-(3-Nitrophenyl)pyrazole is used as a pharmaceutical intermediate for its potential to contribute to the development of new drugs. Its unique structure and pharmacological activities, such as anti-cancer, anti-inflammation, and antimicrobial properties, make it a promising candidate for further research and development in medicinal chemistry.
Used in Organic Synthesis:
In the field of organic synthesis, 3-(3-Nitrophenyl)pyrazole is used as a key building block for the synthesis of a variety of organic compounds. Its reactivity and functional groups allow for the creation of diverse chemical entities, which can be utilized in various applications, including the development of new materials and pharmaceuticals.
Used in Research and Development:
3-(3-Nitrophenyl)pyrazole is employed in research and development for exploring its biological activities and potential applications in drug discovery. Its anti-cancer, anti-inflammatory, and antimicrobial properties are of particular interest, as they may lead to the development of novel therapeutic agents for treating various diseases and conditions.
Overall, 3-(3-Nitrophenyl)pyrazole's versatility in different applications across the pharmaceutical, organic synthesis, and research and development industries highlights its importance and potential in advancing scientific knowledge and creating innovative solutions.

Upstream product

• 645-00-1 m-iodonitrobenzene 
• 197093-16-6 N-tosyl-N-propargylhydrazine 
• 1163721-90-1 3-dimethylamino-1-(3-nitrophenyl)-2-propen-1-one 
• 121-89-1 3-Nitroacetophenone 
• 115955-48-1 3-(dimethylamino)-1-(3-nitrophenyl)-2-propen-1-one 
• 121-90-4 m-nitrobenzoic acid chloride 
• 22107-29-5 1-(3-nitro-phenyl)-ethanone semicarbazone 
• 68-12-2 N,N-dimethyl-formamide 
• 302920-00-9 1-(3-nitrophenyl)-2-propyn-1-one 
• 22553-91-9 trans-3-Diazo-1-(3-nitrophenyl)-propen 

Downstream Products

• 59843-78-6 N,N-dimethyl-2-[3-(3-nitro-phenyl)-pyrazol-1-yl]-propionamide 
• 1206835-70-2 4-iodo-3-(3-nitrophenyl)-1H-pyrazole 
• 1025833-51-5 tert-butyl 5-(3-nitrophenyl)-1H-pyrazole-1-carboxylate 
• 1415913-69-7 7-nitro-3,4-diphenylpyrazolo[5,1-a]isoquinoline 
• 89260-46-8 5⁽³⁾-(3-aminophenyl)-1H-pyrazole 
• 1401206-82-3 C₂₃H₂₆N₄O₃ 
• 1240521-75-8 C₁₈H₁₈N₄O 
• 1240521-76-9 C₂₂H₂₁N₅OS 
• 1240521-76-9 (2S)-N-(3-(1H-pyrazol-3-yl)phenyl)-3-phenyl-2-(thiazol-4-ylmethylamino)propanamide 
• 1240521-75-8 (2S)-N-(3-(1H-pyrazol-3-yl)phenyl)-2-amino-3-phenylpropanamide 
• 89260-46-8 3-(3-Aminophenyl)-pyrazole 

Relevant academic research and scientific papers

Design, synthesis, in silico, and in vitro evaluation of 3-phenylpyrazole acetamide derivatives as antimycobacterial agents

Mycobacterium tuberculosis (Mtb) is one of the most dangerous pathogens affecting immunocompetent and immunocompromised patients worldwide. Novel molecules, which are efficient and can reduce the duration of therapy against drug-resistant strains, are an

Consecutive three-component synthesis of 3-(hetero)aryl-1H-pyrazoles with propynal diethylacetal as a three-carbon building block

A novel consecutive three-component synthesis of 3-(hetero)aryl-1H- pyrazoles via room temperature Sonogashira arylation of propynal diethylacetal used as a propargyl aldehyde synthetic equivalent has been disclosed. The final acetal cleavage-cyclocondensation with hydrazine hydrochloride at 80 °C rapidly furnishes the title compounds in a one-pot fashion.

3,4-DIARYLPYRAZOLES AS PROTEIN KINASE INHIBITORS

3,4-diarylpyrazole derivatives of formula (I) as defined in the specification, and pharmaceutically acceptable salts thereof, process for their preparation and pharmaceutical compositions comprising them are disclosed; the compounds of the invention may be useful, in therapy, in the treatment of diseases associated with a disregulated protein kinase activity, like cancer.

3-AZABICYCLO [3.1.0] HEXANE DERIVATIVES AS VANILLOID RECEPTOR LIGANDS

The present invention relates to 3-azabicyclo[3.1.0]hexane derivatives, which are useful as vanilloid receptor (VR) ligands, methods of treating diseases, conditions and/or disorders modulated by vanilloid receptors with them, and processes for preparing them.

Synthesis of 3-substituted arylpyrazole-4-carboxylic acids

A method was suggested for preparing previously unknown 3-aryl-substituted pyrazole-4-carboxylic acids, involving Vilsmeier formylation of semicarbazones of 26 available mono- and disubstituted acetophenones and 2-acetylthiophene followed by oxidation of

The α-effect in reactions of sp-hybridized carbon atom: Michael-type reactions of 1-aryl-2-propyn-1-ones with primary amines

Second-order rate constants (kN) have been measured for the Michael-type reaction of 1-(X-substituted phenyl)-2-propyn-1-ones (2a-f) with a series of primary amines in H2O at 25.0 ± 0.1 °C. A linear Bronsted-type plot with a small βnuc value (βnuc = 0.30) has been obtained for the reactions of 1-phenyl-2-propyn-1-one (2c) with non-α-nucleophile amines. Hydrazine is more reactive than other primary amines of similar basicity (e.g., glycylglycine and glycine ethyl ester) and results in a positive deviation from the linear Bronsted-type plot. The reactions of 2a-f with hydrazine exhibit a linear Hammett plot, while those with non-α-nucleophile amines give linear Yukawa-Tsuno plots, indicating that the electronic nature of the substituent X does not affect the reaction mechanism. The α-effect increases as the substituent X in the phenyl ring of 2a-f becomes a stronger electron-donating group. However, the magnitude of the α-effect for the reactions of 2a-f is small (e.g., kNhydrazine/kN glycylglycine = 4.6-13) regardless of the electronic nature of the substituent X. The small βnuc has been suggested to be responsible for the small α-effect. A solvent kinetic isotope effect (e.g., kNH2O/kND2O = 1.86) was observed for the reaction with hydrazine but absent for the reactions with non-α-nucleophile amines. The reactions with hydrazine and other primary amines have been suggested to proceed through a five-membered intramolecular H-bonding structure VI and a six-membered intermolecular H-bonding structure VII, respectively. The transition state modeled on VI can account for the substituent dependent α-effect and the difference in the solvent kinetic isotope effect exhibited by the reactions with hydrazine and other primary amines. It has been proposed that the βnuc value is more important than the hybridization type of the reaction site to determine the magnitude of the α-effect.

N-phenylamidines as selective inhibitors of human neuronal nitric oxide synthase: Structure-activity studies and demonstration of in vivo activity

Selective inhibition of the neuronal isoform of nitric oxide synthase (NOS) compared to the endothelial and inducible isoforms may be required for treatment of neurological disorders caused by excessive production of nitric oxide. Recently, we described N-(3-(aminomethyl)benzyl)acetamidine (13) as a slow, tight-binding inhibitor, highly selective for human inducible nitric oxide synthase (iNOS). Removal of a single methylene bridge between the amidine nitrogen and phenyl ring to give N-(3- (aminomethyl)phenyl)acetamidine (14) dramatically altered the selectivity to give a neuronal selective nitric oxide synthase (nNOS) inhibitor. Part of this large shift in selectivity was due to 14 being a rapidly reversible inhibitor of iNOS in contrast to the essentially irreversible inhibition of iNOS observed with 13. Structure-activity studies revealed that a basic amine functionality tethered to an aromatic ring and a sterically compact amidine are key pharmacophores for this class of NOS inhibitors. Maximal nNOS inhibition potency was achieved with N-(3-(aminomethyl)phenyl)-2- furanylamidine (77) (K(i-nNOS) = 0.006 μM; K(i-eNOS) = 0.35 μM; K(i-iNOS) = 0.16 μM). Finally, α-fluoro-N-(3-(aminomethyl)phenyl)acetamidine (74) (K(i- nNOS) = 0.011 μM; K(i-eNOS) = 1.1 μM; K(i-iNOS) = 0.48 μM) had excellent brain penetration and inhibited nNOS in a rat brain slice assay as well as in the rat brain (cerebellum) in vivo. Thus, N-phenylamidines should be useful in validating the role of nNOS in neurological disorders.

Functionalised Pyrazoles through a Facile One-Pot Procedure from N-Tosyl-N-propargylhydrazine and Aryl Iodides or Vinyl Triflates

Functionalised pyrazoles have been prepared in good overall yield through a facile one-pot procedure. The synthesis includes the palladium-catalysed coupling of the readily available N-tosyl-N-propargylhydrazine with aryl iodides or vinyl triflates, the palladium-catalysed annulation of the resulting N-tosyl-N-(1-aryl/vinyl-1-propyn3-yl)hydrazine and exposure of the reaction mixture arising from the annulation step to KOBut.