85-90-5

Usage

Uses

Used in Pharmaceutical Industry:
3-Methylchromone is used as an anti-inflammatory agent for its ability to inhibit inflammation, which can be beneficial in treating various inflammatory conditions.
3-Methylchromone is used as an anti-cancer agent for its potential to inhibit tumor growth, making it a promising candidate for cancer treatment.
Used in Neuroprotection:
3-Methylchromone is used as a neuroprotective agent for its potential to protect neurons from damage, which can be useful in treating neurodegenerative diseases.
Used in Antioxidant Applications:
3-Methylchromone is used as an antioxidant agent for its potential to neutralize harmful free radicals, which can help prevent oxidative stress and related health issues.

InChI:InChI=1/C10H8O2/c1-7-6-12-9-5-3-2-4-8(9)10(7)11/h2-6H,1H3

Upstream product

• 104094-15-7 3-methyl-4-oxo-4H-chromene-2-carboxylic acid 
• 610-99-1 1-(2-Hydroxy-phenyl)-propan-1-on 
• 109-94-4 formic acid ethyl ester 
• 139449-29-9 3-methyl-3-(phenylsulfonyl)chroman-4-one 
• 17422-74-1 3-Formylchromone 
• 122-51-0 orthoformic acid triethyl ester 
• 153933-58-5 o-(1,2-propanedienyloxy)benzaldehyde 
• 29978-83-4 o-propargyloxybenzaldehyde 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 16982-86-8 3-methyl-chroman-4-one 
• 28752-82-1 2-(allyloxy)benzaldehyde 
• 123-54-6 acetylacetone 
• 90-02-8 salicylaldehyde 
• 2985-33-3 monoethyl methylmalonate 

Downstream Products

• 118450-20-7 3-(2-hydroxyphenyl)-4-methyl-1-thicarbamyl-5-thiosemicarbazide-2-pyrazoline 
• 67363-57-9 4-methyl-5-(o-hydroxyphenyl)-isoxazole 
• 89047-15-4 2-amino-3-methyl-4H-chromen-4-one 
• 89296-04-8 2-(4-methyl-1,2-thiazol-5-yl)phenol 
• 94268-36-7 3-(2-hydroxyphenyl)-4-methylpyrazole 
• 118450-21-8 3-(2-hydroxyphenyl)-4-methyl-1-thiocarbamylpyrazole 
• 143707-85-1 5-Ethyl-6-methyl-3-[(4-oxo-4H-chromen-3-ylmethyl)-amino]-1H-pyridin-2-one 
• 130681-11-7 tert-Butyl-dimethyl-[3-methyl-2-(1-phenylsulfanyl-allyl)-2H-chromen-4-yloxy]-silane 
• 1334228-63-5 2-diphenylmethyl-3-methylchromen-4-one 

Relevant academic research and scientific papers

Relay Catalysis by Achiral Borane and Chiral Phosphoric Acid in the Metal-Free Asymmetric Hydrogenation of Chromones

A strategy of relay catalysis by achiral borane and chiral phosphoric acid was successfully developed for the asymmetric hydrogenation of chromones, giving the desired products in high yields with up to 95% ee. Achiral borane and chiral phosphoric acid are highly compatible in this reaction. The achiral borane acts as a Lewis acid for the first-step hydrogenation, and the chiral phosphoric acid acts as an effective chiral proton shuttle to control the enantioselectivity.

Iodine-Mediated Synthesis of 2-(Methylthio)-4 H-chromen-4-ones and Study of Their Halogenation Reactions

An efficient iodine-mediated method is developed for the synthesis of functionalized 2-(methylthio)-4H-chromen-4-ones by intramolecular cyclization of easily accessible 1-(2-benzyloxy-aryl)-3,3-bis-methylsulfanyl-propenones. The synthesized chromen-4-ones turn out to be a key precursor for various kinds of chemical reactions. Mechanistically, we observed that iodine-mediated intramolecular cyclization of ketene dithioacetal proceeded through a radical pathway. 3-Halo-2-(methylthio)-4H-chromen-4-ones were achieved via various two- or one-pot halogenation approaches.

Synthesis of α,β-Disubstituted Acrylates via Galat Reaction

Galat reactions between aldehydes and substituted malonic acids half oxyester were found to be efficiently catalyzed by morpholine in refluxing toluene. This transformation allows the stereoselective synthesis of diverse α,β-disubstituted acrylates in moderate to good yields. This method constitutes an attractive alternative to existing methods in terms of scope and eco-compatibility.

The magnetic graphene oxide/NHC catalyzed aerobic direct amidation and cross-dehydrogenative coupling of aldehydes

In this paper, the synthesis of a novel imidazolium based N-heterocyclic carbene (NHC) containing imidazopyridine substitutes using a three-component reaction is described. This compound was immobilized on magnetic graphene oxide (GO) to make a heterogeneous catalyst for the direct aerobic amidation of benzaldehyde derivatives under solvent-free conditions, as well as the intra-and intermolecular cross dehydrogenative coupling of aldehydes. In addition, the catalytic activity of the NHC catalyst was homogeneously studied in the presence of Fe3O4 nanoparticles under the same conditions, and showed good activity with lower yields than the heterogeneous catalyst.

Silver-Catalyzed Radical Cascade Cyclization toward 1,5-/1,3-Dicarbonyl Heterocycles: An Atom-/Step-Economical Strategy Leading to Chromenopyridines and Isoxazole-/Pyrazole-Containing Chroman-4-Ones

A novel and convenient silver-catalyzed radical cascade cyclization toward a large variety of 1,5-/1,3-dicarbonyl heterocycles containing a chroman-4-one, indanone, or 2,3-dihydroquinolin-4(1H)-one moiety was developed, by reacting various 2-functionalized benzaldehydes, including 2-allyloxy benzaldehydes, 2-allyl benzaldehyde, and 2-N(Ts)CH2-CH CH2 substituted benzaldehyde, with 1,3-dicarbonyl compounds in the presence of AgNO3/K2S2O8 in one pot under mild reaction conditions. The newly obtained 1,5-/1,3-dicarbonyl-containing heterocycles were further used directly to synthesize more structurally diverse polyheterocycles, mainly including chromenopyridines as well as isoxazole- or pyrazole-containing chroman-4-ones.

Synthesis of Enones and Enals via Dehydrogenation of Saturated Ketones and Aldehydes

A general, efficient and economic palladium-catalyzed dehydrogenation to form enones or enals has been developed. The approach possesses extremely broad substrate scope including various linear or cyclic saturated ketones and aldehydes. The protocol is ligand-free, and molecular oxygen is used as the sole clean oxidant in the reaction. Due to mild reaction conditions, good functional group compatibility, and versatile utilities of enones and enals, the method can be applied in the late-stage synthesis of natural products, pharmaceuticals and fine chemicals. (Figure presented.).

Gold nanoparticles on OMS-2 for heterogeneously catalyzed aerobic oxidative α,β-dehydrogenation of β-heteroatom-substituted ketones

In the presence of Au nanoparticles supported on manganese oxide OMS-2 (Au/OMS-2), various kinds of β-heteroatom-substituted α,β-unsaturated ketones (heteroatom = N, O, S) can be synthesized through α,β-dehydrogenation of the corresponding saturated ketones using O2 (in air) as the oxidant. The catalysis of Au/OMS-2 is truly heterogeneous, and the catalyst can be reused.

Synthesis of 3-Substituted Chromones and Quinolones from Enaminones

A facile and efficient synthetic route to 3-substituted chromones and quinolones was developed. Silver triflate was employed to activate the electrophile to react with various readily available enaminones.

The bioinspired design of a reagent allows the functionalization of Cα-H of α,β-unsaturated carbonyl compounds via the Baylis-Hillman chemistry under ambient conditions

A rationally designed reagent capable of affecting alkylation at Cα of α,β-unsaturated carbonyl compounds is reported. The reaction proceeded at room temperature without any additives. The pH and H-bond formation during the reaction play a key role in the working of the reagent.

Exploiting the Chromone Scaffold for the Development of Inhibitors of Corticosteroid Biosynthesis

The inhibition of corticosteroid biosynthesis could be considered as an emerging strategy to reduce their abnormally high levels, and in this framework CYP11B1 and CYP11B2 represent the most promising targets. In continuing our studies on flavonoid-like scaffolds as privileged structures in medicinal chemistry, in this paper we describe a small library of pyridyl- and imidazolylmethylchromones as potential inhibitors of these enzymes. Testing results proved that position 3 of the chromone scaffold is the most favorable for the introduction of the heme-coordinating heterocycles and, among them, the 4-imidazolyl moiety is the most convenient for the interaction with the heme iron of the selected cytochromes. A low nanomolar inhibitor of CYP11B1 (5c) was obtained, endowed with reasonable selectivity toward CYP11B2 and able to better discriminate with respect to CYP17 and CYP19.