709-04-6

Usage

Uses

Used in Medicinal Chemistry:
1-Phenyl-1H-pyrazole-4-carbonitrile is used as a building block for the synthesis of biologically active compounds, contributing to the development of new pharmaceuticals. Its structure allows for versatile chemical modifications, which can lead to the creation of molecules with specific therapeutic properties.
Used in Pharmaceutical Production:
As an intermediate in the production of pharmaceuticals, 1-Phenyl-1H-pyrazole-4-carbonitrile plays a crucial role in the synthesis of various drug candidates. Its presence in the molecular structure can impart desired pharmacological effects, making it an essential component in the development of novel therapeutic agents.
Used in Agrochemical Development:
1-Phenyl-1H-pyrazole-4-carbonitrile is also utilized in the agrochemical industry, where it serves as a key intermediate for the synthesis of bioactive compounds with pesticidal or herbicidal properties. Its incorporation into these molecules can enhance their effectiveness in protecting crops from pests and diseases.
Used in Organic Synthesis Research:
In the field of organic synthesis, 1-Phenyl-1H-pyrazole-4-carbonitrile is employed as a valuable tool for research and development. Its unique chemical properties and reactivity enable chemists to explore new synthetic pathways and develop innovative methods for the preparation of complex organic molecules.
Used in Fine Chemicals Industry:
1-Phenyl-1H-pyrazole-4-carbonitrile finds application in the fine chemicals industry, where it is used as an intermediate for the synthesis of specialty chemicals with specific applications in various sectors, such as fragrances, dyes, and advanced materials. Its versatility and reactivity make it a sought-after component in the production of high-value chemicals.

InChI:InChI=1/C10H7N3/c11-6-9-7-12-13(8-9)10-4-2-1-3-5-10/h1-5,7-8H

Upstream product

• 109-73-9 N-butylamine 
• 99989-15-8 1-phenyl-1Hpyrazole-4-carbaldehyd-(O-acetyl-(Z)-oxime ) 
• 54605-72-0 1-phenyl-1H-pyrazole-4-carbaldehyde 
• 5334-43-0 5-Amino-4-cyano-1-phenylpyrazole 
• 31108-57-3 1H-pyrazole-4-carbonitrile 
• 71-43-2 benzene 
• 35520-41-3 trans-3-dimethylaminoacrylonitrile 
• 59-88-1 phenylhydrazine hydrochloride 
• 1126-00-7 1-phenylpyrazole 
• 149139-41-3 α-cyano-β-dimethylaminoacrolein 
• 100-63-0 phenylhydrazine 
• 98431-59-5 2-(ethoxy-methoxy-methyl)-acrylonitrile 
• 75033-03-3 β,β'-diethoxy-β-methoxy-isobutyronitrile 
• 3699-10-3 2-ethoxymethyl-3c-methoxy-acrylonitrile 

Downstream Products

• 1134-50-5 4-carboxy-1-phenylpyrazole 
• 68287-79-6 1-(4-nitrophenyl)-1H-pyrazole-4-carboxylic acid 
• 137576-90-0 2-<4-(1-Phenylpyrazolyl)>-4-thiazolylcarboxylic acid 
• 137576-96-6 2-<4-(1-Phenylpyrazolyl)>-4-thiazolylacetic acid 
• 137576-89-7 Ethyl 2-<4-(1-phenylpyrazolyl)>-4-thiazolylcarboxylate 
• 1152605-36-1 1-phenyl-1H-pyrazole-4-carboximidamide 
• 3199-05-1 1-phenyl-1H-pyrazole-4-carboxamide 
• 1431459-06-1 5-(1-phenyl-1H-pyrazole-4-yl)-1H-tetrazole 
• 54906-38-6 1-Phenyl-4-pyrazolethiocarboxamide 

Relevant academic research and scientific papers

Synergistic Indium and Silver Dual Catalysis: A Regioselective [2 + 2 + 1]-Oxidative N-Annulation Approach for the Diverse and Polyfunctionalized N-Arylpyrazoles

Indium(III)/silver(I)-catalyzed [2 + 2 + 1] annulation of arylhydrazine hydrochlorides with β-enamino esters via multicomponent reactions for the construction of diverse and multisubstituted N-arylpyrazoles has been demonstrated. The oxidative cycloaddition proceeds via a cascade triple Michael addition/elimination/air oxidation. This novel protocol provides a rapid and efficient synthetic route to various 3,4-diester-substituted N-arylpyrazoles. The synthesized compounds are further utilized for various synthetic transformations.

Synthesis of pyrazole-carboxamides and pyrazole-carboxylic acids derivatives: Simple methods to access powerful building blocks

Hybrid systems containing pyrazole moiety show a wide spectrum of biological activities. To access novel hybrids with pyrazole ring, in this work we synthesized twenty pyrazole-carboxylic acids and twenty pyrazole-carboxamides, using simple synthetic methods, to be used as building blocks in the development of new structures.

Unveiling Potent Photooxidation Behavior of Catalytic Photoreductants

We describe a photocatalytic system that reveals latent photooxidant behavior from one of the most reducing conventional photoredox catalysts, N-phenylphenothiazine (PTH). This aerobic photochemical reaction engages difficult to oxidize feedstocks, such as benzene, in C(sp2)-N coupling reactions through direct oxidation. Mechanistic studies are consistent with activation of PTH via photooxidation and with Lewis acid cocatalysts scavenging inhibitors inextricably formed in this process.

Design, synthesis and pharmacological assessment of new pyrazole compounds

Aims: This study investigated the antinociceptive and anti-inflammatory effects of new pyrazole compounds LQFM011(5), LQFM043(6) and LQFM044(7) as well as the mechanisms of action and acute in vitro toxicity. Main methods: The antinociceptive activity was evaluated using the acetic acid-induced abdominal writhing test, formalin-induced pain test and the Randall–Selitto test. The anti-inflammatory activity was evaluated using models of paw oedema and pleurisy induced by carrageenan; cell migration, the levels of tumour necrosis factor α (TNF-α) and myeloperoxidase (MPO) enzyme activity were evaluated. In addition, the ability to inhibit phospholipase A2 (PLA2) in vitro and docking in PLA2 were used. Acute oral systemic toxicity in mice was evaluated through the neutral red uptake assay. Key findings: The synthesised compounds (5–7), delivered via gavage (p.o.) at 70, 140 or 280 μmol/kg, decreased the number of writhings induced by acetic acid; the three compounds (280 μmol/kg p.o.) reduced the paw licking time in the first and second phase of the formalin test and decreased the nociceptive threshold variation in the Randall–Selitto test. Furthermore, this dose reduced oedema formation, leucocyte migration (specifically through reduction in polymorphonuclear cell movement) and increased mononuclear cells. MPO activity and the levels of pro-inflammatory cytokines TNF-α were decreased. Evaluation of PLA2 inhibition via the docking simulation revealed more interactions of LQFM043R(6) and LQFM044(7), data that corroborated the half-maximal inhibitory concentration (IC50) of PLA2 inhibition in vitro. Therefore, LQFM011(5), LQFM043(6) and LQFM044(7) were classified with the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) as category 4.

A Convenient Synthesis of Pyrazole-imidazoline Derivatives by Microwave Irradiation

A series of 28 hybrids pyrazole-imidazolines 1a–n and 2a–n were synthesized by a new methodology using microwave irradiation, in short time (20–30?min), in low power (50–70?W), and in 34–92% yield. Among all methodologies evaluated, no side products were obtained. All derivatives were completely characterized by FT–IR, 1H and 13C NMR, GC–MS, and HRMS.

PHARMACEUTICAL COMPOUND

Provided is a compound having formula (I): wherein R2 is selected from -C1, -Br and -CN; R1 and R4 are independently selected from H and -F; R631, R632, R641 and R642

Catalytic cyanation of aryl iodides using DMF and ammonium bicarbonate as the combined source of cyanide: A dual role of copper catalysts

Cu(ii)-catalyzed cyanation of aryl iodides has been developed using DMF and ammonium bicarbonate as the combined source of cyanide. It is assumed that copper is involved both in the generation of CN units from DMF-ammonia and in the cyanation of aryl halides. A range of electron-rich and fused (hetero)aryl iodides underwent cyanation resulting in moderate to good yields.

An efficient synthesis of new 5-(1-Aryl-1H-pyrazole-4-yl)-1H-tetrazoles from 1-Aryl-1H-pyrazole-4-carbonitriles via [3 + 2] cycloaddition reaction

A series of new 5-(1-aryl-1H-pyrazole-4-yl)-1H-tetrazoles 4a-l were synthesized via [3 + 2] cycloaddition reaction from 1-aryl-1H-pyrazole-4- carbonitriles 3a-l, sodium azide and ammonium chloride, using dimethylformamide (DMF) as solvent, in good yields: 64-85%. The structures of these newly synthesized compounds were determined from the IR, 1H- and 13C-NMR spectroscopic data and elemental analyses.

Synthesis and antileishmanial activity of new 1-aryl-1H-pyrazole-4- carboximidamides derivatives

Chemotherapy for leishmaniasis, diseases caused by protozoa of the genus Leishmania, remains inefficient in several treatments. So there is a need to search for new drugs. In this work, we have synthesized 1-aryl-1H-pyrazole-4- carboximidamides derivatives and evaluated antileishmanial activities in vitro, as well as cytotoxic effects. Structure-activity relationship (SAR) studies were carried out with all the compounds of the series. Compound 2 showed an activity profile that can be improved through medicinal chemistry strategies.

Synthesis and antileishmanial evaluation of 1-aryl-4-(4,5-dihydro-1H- imidazol-2-yl)-1H-pyrazole derivatives

A series of 1-aryl-4-(4,5-dihydro-1H-imidazol-2-yl)-1H-pyrazoles (4a-g) and 5-amino-1-aryl-4-(4,5-dihydro-1H-imidazol-2-yl)-1H-pyrazoles (5a-g) were synthesized and evaluated in vitro against three Leishmania species: L. amazonensis, L. braziliensis and L. infantum (L. chagasi syn.). The cytotoxicity was assessed. Among the derivatives examined, six compounds emerged as the most active on promastigotes forms of L. amazonensis with IC50 values ranging from 15 to 60 μM. The reference drug pentamidine presented IC 50 = 10 μM. However, these new compounds were less cytotoxic than pentamidine. Based on these results, the more promising derivative 5d was tested further in vivo. This compound showed inhibition of the progression of cutaneous lesions in CBA mice infected with L. amazonensis relative to an untreated control.