3327-27-3

Usage

Uses

Used in Pharmaceutical Industry:
2-(pyridin-3-yl)-4H-chromen-4-one is used as a potential therapeutic agent for various health conditions due to its anti-inflammatory, anti-cancer, and anti-microbial properties. Its ability to modulate biological processes and target specific pathways makes it a promising candidate for the development of new drugs.
Used in Bioanalytical Research:
2-(pyridin-3-yl)-4H-chromen-4-one is used as a fluorescent probe for detecting metal ions in biological systems. Its unique chemical properties allow it to interact with metal ions, making it a valuable tool for researchers in the field of bioanalysis and environmental monitoring.
Used in Material Science:
2-(pyridin-3-yl)-4H-chromen-4-one is used as a component in the development of new materials with potential applications in various industries. Its chemical structure and properties can be exploited to create materials with specific characteristics, such as improved stability or enhanced reactivity.

Upstream product

• 6296-04-4 1-(2-hydroxyphenyl)-3-(pyridine-3-yl)propane-1,3-dione 
• 59-67-6 nicotinic acid 
• 2875-25-4 1-(2-hydroxyphenyl)-3-(pyridin-3-yl) prop-2-en-1-one 
• 2510-23-8 3-Ethynylpyridine 
• 533-58-4 2-Iodophenol 
• 201230-82-2 carbon monoxide 
• 90-02-8 salicylaldehyde 
• 500-22-1 3-pyridinecarboxaldehyde 
• 3034-12-6 2-(pyridin-3-yl)chroman-4-one 
• 118-93-4 o-hydroxyacetophenone 
• 626-55-1 3-Bromopyridine 
• 64531-95-9 nicotinoyl ethylcarbonate 
• 92163-69-4 2-Nicotinoyloxy-acetophenon 
• 20260-53-1 pyridine-3-carbonyl chloride hydrochloride 

Downstream Products

• 65010-79-9 2-(3-(pyridin-3-yl)isoxazol-5-yl)phenol 

Relevant academic research and scientific papers

Thallium(III) p-tosylate-mediated oxidative [1,2] rearrangement of 2-naphthyl and 2-heteroarylchromanones

A practical and effective approach towards the synthesis of 3-heteroaryl-4H-chromen-4-ones by the oxidative [1,2] rearrangement of the respective 2-heteroaryl chroman-4-ones using thallium(III) p-tosylate is presented. The oxidative rearrangement of α- an

Nickel catalysed carbonylative Sonogashira reaction for the synthesis of diarylalkynones and 2-substituted flavones

The nickel catalyzed, palladium/phosphine free carbonylative Sonogashira reaction of terminal alkynes with substituted aryl and heteroaryl iodides is described. This protocol provides mild and robust conditions to synthesize a variety of substituted aryl α,β-alkynyl ketones and flavones in good to excellent isolated yields. This methodology tolerates several functional groups such as electron donating (methyl, isopropyl, tert-butyl, methoxy) as well as electron withdrawing (trifluoromethyl, nitro, esters, nitrile) groups on the terminal alkynes and iodides.

An efficient oxidative conversion of 2-aryl-2H-chromenes to the corresponding flavones by tert-butylhydroperoxide and copper bromide

A simple and efficient method has been developed for the facile oxidation of chromenes to the corresponding flavones by tert-butylhydroperoxide (TBHP) in the presence of copper(II) bromide catalyst in toluene at 80 °C in a very short time. The reaction demonstrates excellent reactivity, functional group tolerance, and good to excellent yields without using conventional strong oxidizing agents.

Synthesis and antiviral activity of 2-aryl-4H-chromen-4-one derivatives against Chikungunya virus

A series of nineteen 2-aryl-4H-chromen-4-one derivatives 2a-2s were synthesized and evaluated for their antiviral activity against Chikungunya virus (LR2006-OPY1) in Vero cell culture by CPE reduction assay. Three compounds 2a, 2b and 2g, were found to be active at concentration of (IC50) 0.44 μM, 0.45 μM and 2.02 μM, respectively. Compounds having heterocyclic ring 2a and 2b at the 2nd position of the chromenone were found to be potent inhibitor of ChikV. Cytotoxicity studies were performed using Vero cell culture, compounds 2a and 2b exhibited SI of ≥100. Molecular docking simulation has been carried out to understand the possible mechanism of action.

Ru(II)-catalyzed C-H activation and annulation of salicylaldehydes with monosubstituted and disubstituted alkynes

The Ru(ii)-catalyzed C-H activation and annulation reaction of salicylaldehydes and disubstituted alkynes affords chromones in high yields. This reaction also works with terminal alkynes and tolerates a wide range of sensitive functional groups. The selectivity pattern of this Ru(ii)-catalyzed annulation reaction is different from the known Au(i), Rh(iii)-catalyzed annulation reactions of salicylaldehydes and terminal alkynes.

Highly efficient synthesis of flavones: Via Pd/C-catalyzed cyclocarbonylation of 2-iodophenol with terminal acetylenes

A highly efficient and selective Pd/C-catalyzed ligand-free cyclocarbonylation reaction for the synthesis of flavones has been developed. Various flavone derivatives were isolated in excellent yields with excellent functional group tolerances. Additionally, catalyst reuse experiments were performed successfully as well.

Raf kinase inhibitor based on chromone structure, and preparation method and uses thereof

The invention relates to the technical field of pharmaceutical chemistry, and more concretely relates to a group of chromone compounds (A), wherein R1-R10, X1 and X2 are defined in the description. The invention also discloses a preparation method of the

Monoamine oxidase inhibitory activity of 2-aryl-4H-chromen-4-ones

A series of twenty 2-aryl-4H-chromen-4-one (flavones) derivatives (3a-3s) were synthesized and tested for hMAO inhibitory activity. Fifteen compounds (3a, 3c, 3e-3h, 3j-3p, 3r, 3s) were found to be selective towards MAO-B, while 3d was selective towards MAO-A, and 3b, 3i and 3q were non-selective. Experimental Selectivity Index for MAO-B ranges from 2.0 (3g, 3p) to 30.0 (3j). Compound 3j, which is carrying 3,4-di-OMeC6H3 groups at R position on the molecule, was found to be potent MAO-B inhibitor amongst the fifteen with Ki value for MAO-B of 0.16 ± 0.01 lM comparable to that of standard drug, Selegiline (Ki for MAO-B is 0.16 ± 0.01 μM). Compound 3j also appeared as the most selective MAO-B inhibitor according to its best selectivity index (30.0), which is comparable to that of Selegiline (SIMAO-B = 35.0). Molecular docking and molecular dynamics simulation studies were carried out using Autodock-4.0 and Amber12 to understand the molecular level interaction and energy relation of MAO isoforms with selective inhibitors (3d and 3j). Simulation results are in good agreement with the experimental results. Leads identified may further be explored to develop potent isoform specific inhibitors of MAO.

Monoamine oxidase inhibitory activity of 2-aryl-4H-chromen-4-ones

A series of twenty 2-aryl-4H-chromen-4-one (flavones) derivatives (3a-3s) were synthesized and tested for hMAO inhibitory activity. Fifteen compounds (3a, 3c, 3e-3h, 3j-3p, 3r, 3s) were found to be selective towards MAO-B, while 3d was selective towards MAO-A, and 3b, 3i and 3q were non-selective. Experimental Selectivity Index for MAO-B ranges from 2.0 (3g, 3p) to 30.0 (3j). Compound 3j, which is carrying 3,4-di-OMeC6H3 groups at R position on the molecule, was found to be potent MAO-B inhibitor amongst the fifteen with Ki value for MAO-B of 0.16 ± 0.01 μM comparable to that of standard drug, Selegiline (Ki for MAO-B is 0.16 ± 0.01 μM). Compound 3j also appeared as the most selective MAO-B inhibitor according to its best selectivity index (30.0), which is comparable to that of Selegiline (SIMAO-B = 35.0). Molecular docking and molecular dynamics simulation studies were carried out using Autodock-4.0 and Amber12 to understand the molecular level interaction and energy relation of MAO isoforms with selective inhibitors (3d and 3j). Simulation results are in good agreement with the experimental results. Leads identified may further be explored to develop potent isoform specific inhibitors of MAO.

Synthesis and antimicrobial activity of 2-(pyridine-3-yl)-4 H -chromen-4-one derivatives

An efficiently synthesis of chromones via cyclodehydration of corresponding 1-(2-hydroxyphenyl)-3-(pyridine-3-yl)propane-1,3-dione is described under ultrasound irradiation. A series of novel 2-(pyridine-3-yl)-4H-chromen-4-one derivatives was confirmed on the basis of 1H-NMR, mass, IR spectral data, and elemental analysis. The synthesized compounds were evaluated for their antibacterial and antifungal activities. Most of the compounds were found to be comparable potent than the reference standard drugs. Utilization of ultrasound irradiation, simple reaction conditions, isolation, and purification makes this manipulation very interesting from an economic and environmental perspective.