1493-47-6

Usage

Structure

Pyrazole ring substituted with two 4-fluorophenyl groups at positions 3 and 5

Type

Pyrazole derivative

Use in pharmaceutical research and development

Potential as a potent and selective inhibitor of certain enzymes

Applications

Materials science and organic synthesis

Safety precautions

Handle with care, prolonged or repeated exposure may lead to potential health hazards.

Upstream product

• 102692-35-3 4,4'-difluorochalcone 
• 459-57-4 4-fluorobenzaldehyde 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 2714-90-1 phenyl 4-fluorobenzoate 
• 401514-49-6 [(4-fluorophenyl)methylidene]hydrazine 
• 403-33-8 methyl 4-flurobenzoate 
• 403-43-0 4-fluorobenzoyl chloride 
• 2805-56-3 (2E)-1,3-bis(4-fluorophenyl)prop-2-en-1-one 
• 1493-51-2 1,3-bis-(4-fluoro-phenyl)-1,3-propanedione 

Downstream Products

• 1439308-82-3 C₁₈H₁₄F₂N₂O₂ 
• 1440951-91-6 1-(2-amino-4,5,7,8-tetrahydro-thiazolo (4,5-d) azepin-6-yl)-2-[3,5-bis-(4-fluorophenyl)pyrazol-1-yl]ethanone 
• 1439311-91-7 (3,5-bis-(4-fluorophenyl)-pyrazol-1-yl)-acetic acid 

Relevant academic research and scientific papers

Synthesis and theoretical study of a series of 3,5-disubstitutes pyrazoles

In this work, we proposed the synthesis of a series of pyrazoles derivatives with different substituents on the aromatic rings. We aim to evaluate their influence on the reactivity of the compounds in reactions of α,β-unsaturated chalcones and sulfonyl hydrazide catalyzed by iodine. In order to explain their high and low yields, or the impossibility of obtaining some compounds by applied synthetic methodology, Density Functional Theory (DFT) calculations were performed. The reaction Gibbs free energy (ΔG) as well as the energy gap of the HOMO-LUMO frontier orbitals (ΔE) of some selected reactants could explain qualitatively the experimental observations in terms of synthesis yield. In this way, we believe that the chemical nature of aromatic ring substituents is relevant for the reactivity of the starting materials as well as the formation of the desired products.

Denitrative imino-diaza-Nazarov cyclization: Synthesis of pyrazoles

An iodine-catalyzed denitrative imino-diaza-Nazarov cyclization (DIDAN) methodology has been developed for the synthesis of pyrazoles with high to excellent yields by using α-nitroacetophenone derivatives and in situ generated hydrazones. The key transformation of this oxidative 4π-electrocyclization proceeds through an enamine-iminium ion intermediate. This rapid one-pot DIDAN protocol results in the selective generation of C-C and C-N bonds and cleavage of a C-N bond. This journal is

The diaza-Nazarov cyclization involving a 2,3-diaza-pentadienyl cation for the synthesis of polysubstituted pyrazoles

An unprecedented iodine-mediated diaza-Nazarov (DAN) type cyclization for the construction of substituted pyrazoles from easily available starting materials via an enamine-iminium ion intermediate is described. The oxidative cyclization worked under green conditions with remarkable regioselectivity. This one-pot, efficient and operationally simple three-component intramolecular regioselective DAN cyclization displayed a wide range of substrate scope. The dichotomy of reaction pathways has been explored with density functional theory in the gas phase and solution phase. Of the possible 1,5-, 1,6-, and 1,7-electrocyclizations, the DAN cyclization, i.e., the 1,5-pathway offers the lowest activation energy barrier supporting our experimental observations.

NOVEL COMPOUNDS

This invention relates to compounds of formula I their use as positive allosteric modulators of mGlu5 receptor activity, pharmaceutical compositions containing the same, and methods of using the same as agents for treatment and/or prevention of neurological and psychiatric disorders associated with glutamate dysfunction such as schizophrenia or cognitive decline such as dementia or cognitive impairment. A, B, X, R1, R2, R3 have meanings given in the description.

NOVEL COMPOUNDS

This invention relates to compounds of formula (I) their use as positive allosteric modulators of mGlu5 receptor activity, pharmaceutical compositions containing the same, and methods of using the same as agents for treatment and/or prevention of neurological and psychiatric disorders associated with glutamate dysfunction such as schizophrenia or cognitive decline such as dementia or cognitive impairment. A, B, Ar, R1, R2, R3 have meanings given in the description.

NOVEL COMPOUNDS

This invention relates to compounds of formula I their use as positive allosteric modulators of mGlu5 receptor activity, pharmaceutical compositions containing the same, and methods of using the same as agents for treatment and/or prevention of neurological and psychiatric disorders associated with glutamate dysfunction such as schizophrenia or cognitive decline such as dementia or cognitive impairment. A, B, Ar, R1, R2, R3 have meanings given in the description.

New one step synthesis of 3,5-disubstituted pyrazoles under microwave irradiation and classical heating

(Chemical Equation Presented) A convenient one pot procedure for the synthesis of 3,5-disubstituted pyrazoles by condensation of chalcones, hydrazine hydrate and sulfur in ethanol under microwave irradiation and conventional heating method is reported. The hydrogen sulfide is produced during the reaction. The pyrazoles are obtained in good yields and excellent state of purity. The structures of new compounds were confirmed by IR, 1H, and 13C NMR, MS and elemental analysis.

Monoamine oxidase isoform-dependent tautomeric influence in the recognition of 3,5-diaryl pyrazole inhibitors

A series of 3,5-diaryl pyrazoles were prepared and assayed for their ability to inhibit reversibly monoamine oxidase-A (MAO-A) and monoamine oxidase B (MAO-B). Several compounds show inhibitory activity with concentration values in the nanomolar range. A computational work was carried out on the two most selective inhibitors that have tautomeric pyrazole forms. The binding free energies of these compounds for each MAO isoform were influenced by the tautomeric equilibria.