25870-68-2

Usage

Uses

Used in Organic Synthesis:
3-(4-METHYLPHENYL)-1-(3-NITROPHENYL)PROP-2-EN-1-ONE is used as a key intermediate in organic synthesis for its ability to participate in various chemical reactions. Its α,β-unsaturated ketone structure makes it a versatile building block for the creation of complex organic molecules.
Used in Pharmaceutical Industry:
3-(4-METHYLPHENYL)-1-(3-NITROPHENYL)PROP-2-EN-1-ONE is used as a potential active pharmaceutical ingredient due to its studied biological activities. It has been investigated for its anti-inflammatory and antimicrobial properties, making it a candidate for the development of new drugs targeting these therapeutic areas.
Used in Chemical Research:
In the field of chemical research, 3-(4-METHYLPHENYL)-1-(3-NITROPHENYL)PROP-2-EN-1-ONE serves as a subject of study for understanding the reactivity and behavior of α,β-unsaturated ketones. Its unique structure allows researchers to explore new reaction pathways and mechanisms, contributing to the advancement of organic chemistry.

InChI:InChI=1/C16H13NO3/c1-12-5-7-13(8-6-12)9-10-16(18)14-3-2-4-15(11-14)17(19)20/h2-11H,1H3/b10-9+

Upstream product

• 104-87-0 4-methyl-benzaldehyde 
• 121-89-1 3-Nitroacetophenone 

Downstream Products

• 25870-78-4 4-Methyl-3'-aminochalcon 
• 25870-93-3 4-Methyl-3'-isothiocyanatochalcon 
• 1421504-73-5 3-(3-nitrophenyl)-5-p-tolyl-4,5-dihydroisoxazole 

Relevant academic research and scientific papers

Design, synthesis and mechanistic study of novel diarylpyrazole derivatives as anti-inflammatory agents with reduced cardiovascular side effects

Novel diarylpyrazole (5a-d, 6a-e, 12, 13, 14, 15a-c and 11a-g) derivatives were designed, synthesized and evaluated for their dual COX-2/sEH inhibitory activities via recombinant enzyme assays to explore their anti-inflammatory activities and cardiovascular safety profiles. Comprehensively, the structures of the synthesized compounds were established via spectral and elemental analyses, followed by the assessment of both their in vitro COX inhibitory and in vivo anti-inflammatory activities. The most active compounds as COX inhibitors were further evaluated for their in vitro 5-LOX and sEH inhibitory activities, alongside with their in vivo analgesic and ulcerogenic effects. Compounds 6d and 11f showed excellent inhibitory activities against both COX-2 and sEH (COX-2 IC50 = 0.043 and 0.048 μM; sEH IC50 = 83.58 and 83.52 μM, respectively). Moreover, the compounds demonstrated promising results as anti-inflammatory and analgesic agents with considerable ED50 values and gastric safety profiles. Remarkably, the most active COX inhibitors 6d and 11f possessed improved cardiovascular safety profiles, if compared to celecoxib, as shown by the laboratory evaluation of both essential cardiac biochemical parameters (troponin-1, prostacyclin, tumor necrosis factor-α, lactate dehydrogenase, reduced glutathione and creatine kinase-M) and histopathological studies. On the other hand, docking simulations confirmed that the newly synthesized compounds displayed sufficient structural features required for binding to the target COX-2 and sEH enzymes. Also, in silico ADME studies prediction and drug-like properties of the compounds revealed favorable oral bioavailability results. Collectively, the present work could be featured as a promising future approach towards novel selective COX-2 inhibitors with declined cardiovascular risks.

Synthesis, cyclooxygenase inhibition and anti-inflammatory evaluation of new 1,3,5-triaryl-4,5-dihydro-1H-pyrazole derivatives possessing methanesulphonyl pharmacophore

A new series of 1,3,5-triaryl-4,5-dihydro-1H-pyrazole derivatives 13a–p were synthesized via aldol condensation of 3/4-nitroacetophenones with appropriately substituted aldehydes followed by cyclization of the formed chalcones with 4-methanesulfonylphenylhydrazine hydrochloride. All the synthesized compounds were evaluated for their cyclooxygenase (COX) inhibition, anti-inflammatory activity and ulcerogenic liability. All compounds were more potent inhibitors for COX-2 than COX-1. While most compounds showed good anti-inflammatory activity, compounds 13d, 13f, 13k and 13o were the most potent derivatives (ED50 = 66.5, 73.4, 79.8 and 70.5 μmol/kg, respectively) in comparison with celecoxib (ED50 = 68.1 μmol/kg). Compounds 13d, 13f, 13k and 13o (ulcer index = 3.89, 4.86, 4.96 and 3.92, respectively) were 4–6 folds less ulcerogenic than aspirin (ulcer index = 22.75) and showed approximately ulceration effect similar to celecoxib (ulcer index = 3.35). In addition, molecular docking studies were performed for compounds 13d, 13f, 13k and 13o inside COX-2 active site which showed acceptable binding interactions (affinity in kcal/mol ?2.1774, ?6.9498) in comparison with celecoxib (affinity in kcal/mol ?6.5330).

Synthesis, characterization and biological evaluation of some new isoxazoline derivatives

Isoxazoline represents a unique class of nitrogen- and oxygen-containing five-membered heterocycles, a class of compounds of great importance in biological chemistry. Isoxazoline is considered as one of the most potent antimicrobial compound. Isoxazoline