3952-69-0

Usage

Uses

Used in Pharmaceutical Industry:
5-HYDROXY-4H-CHROMEN-4-ONE is used as an active pharmaceutical ingredient for its potential medicinal properties, such as its antioxidant, anti-inflammatory, and anti-cancer effects. It is being studied for its potential use in the treatment of diabetes and its ability to protect against various neurological disorders.
Used in Organic Synthesis:
5-HYDROXY-4H-CHROMEN-4-ONE is used as a key intermediate in the synthesis of other organic compounds, contributing to the development of new pharmaceuticals and chemical products.
Used in Antioxidant Applications:
5-HYDROXY-4H-CHROMEN-4-ONE is used as an antioxidant agent, helping to protect cells from oxidative stress and damage, which can contribute to various diseases and aging processes.
Used in Anti-Inflammatory Applications:
5-HYDROXY-4H-CHROMEN-4-ONE is used as an anti-inflammatory agent, potentially reducing inflammation and alleviating symptoms associated with inflammatory conditions.
Used in Anticancer Applications:
5-HYDROXY-4H-CHROMEN-4-ONE is used as an anticancer agent, being studied for its potential to inhibit cancer cell growth and proliferation, and to modulate various oncological signaling pathways.
Used in Diabetes Treatment:
5-HYDROXY-4H-CHROMEN-4-ONE is used as a potential therapeutic agent in the treatment of diabetes, with research investigating its ability to improve insulin sensitivity and glucose metabolism.

InChI:InChI=1/C9H6O3/c10-6-2-1-3-8-9(6)7(11)4-5-12-8/h1-5,10H

Upstream product

• 491-38-3 1-benzopyran-4(4H)-one 
• 118-93-4 o-hydroxyacetophenone 
• 109-94-4 formic acid ethyl ester 
• 699-83-2 2,6-dihydroxylacetophenone 
• 68-12-2 N,N-dimethyl-formamide 
• 108-46-3 recorcinol 
• 122-51-0 orthoformic acid triethyl ester 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 13849-19-9 5-hydroxy-3,4-dihydro-2H-1-benzopyran-4-one 
• 133992-43-5 3,4-dihydrofuro<4,3,2-de><1>benzopyran 
• 13849-32-6 3,4-dihydro-5-hydroxy-2H-1-benzopyran 
• 59887-87-5 5-methoxy-4H-chromen-4-one 

Relevant academic research and scientific papers

PYRAZOLYLBENZENE-1,3-DIOLS FOR DISEASES ASSOCIATED WITH G PROTEIN-COUPLED RECEPTOR 18 AND IN COMBINATION WITH TRANSIENT RECEPTOR POTENTIAL VANILLOID 1

The present invention relates to pyrazolylbenzene-1,3-diols as cannabidiol derivatives, its use for the manufacture of a medicament, and more particularly, to the use of this medicament for the treatment and/or prevention of a disorder associated with the GPR18 and/or TRPV1 receptors and the use of these compounds for pharmacological assays related to GPR18 and/or TRPV1.

Synthesis and evaluation of trypanocidal activity of chromane-type compounds and acetophenones

American trypanosomiasis (Chagas disease) caused by the Trypanosoma cruzi parasite, is a severe health problem in different regions of Latin America and is currently reported to be spreading to Europe, North America, Japan, and Australia, due to the migration of populations from South and Central America. At present, there is no vaccine available and chemotherapeutic options are reduced to nifurtimox and benznidazole. Therefore, the discovery of new molecules is urgently needed to initiate the drug development process. Some acetophenones and chalcones, as well as chromane-type substances, such as chromones and flavones, are natural products that have been studied as trypanocides, but the relationships between structure and activity are not yet fully understood. In this work, 26 compounds were synthesized to determine the effect of hydroxyl and isoprenyl substituents on trypanocide activity. One of the compounds showed interesting activity against a resistant strain of T. cruzi, with a half effective concentration of 18.3 μM ± 1.1 and an index of selectivity > 10.9.

PYRAZOLYLBENZENE-1,3-DIOLS FOR DISEASES ASSOCIATED WITH G PROTEIN-COUPLED RECEPTOR 18 AND IN COMBINATION WITH TRANSIENT RECEPTOR POTENTIAL VANILLOID 1

The present invention relates to pyrazolylbenzene-1,3-diols as cannabidiol derivatives, its use for the manufacture of a medicament, and more particularly, to the use of this medicament for the treatment and/or prevention of a disorder associated with the GPR18 and/or TRPV1 receptors and the use of these compounds for pharmacological assays related to GPR18 and/or TRPV1.

Second Generation Total Synthesis of (–)-Preussochromone D

An improved enantioselective synthesis of the natural product (–)-preussochromone D (3) and first insights into a possible route to the trans-preussochromones E and F are described. Starting from commercially available 5-hydroxy-4H-chromen-4-one, two ster

Natural products as sources of new fungicides (V): Design and synthesis of acetophenone derivatives against phytopathogenic fungi in vitro and in vivo

A series of acetophenone derivatives (10a–10i, 11, 12a–12g, 13a–13g, 14a–14d and 15a–15l) were designed, synthesized and evaluated for antifungal activities in vitro and in vivo. The antifungal activities of 53 compounds were tested against several plant pathogens, and their structure–activity relationship was summarized. Compounds 10a–10f displayed better antifungal effects than two reference fungicides. Interestingly, the most potent compound 10d exhibited antifungal properties against Cytospora sp., Botrytis cinerea, Magnaporthe grisea, with IC50 values of 6.0–22.6 μg/mL, especially Cytospora sp. (IC50 = 6.0 μg/mL). In the in vivo antifungal assays, 10d displayed the significant protective efficacy of 55.3% to Botrytis cinerea and 73.1% to Cytospora sp. The findings indicated that 10d may act as a potential pesticide lead compound that merits further investigation.

Ru(II)-Catalyzed Site-Selective Hydroxylation of Flavone and Chromone Derivatives: The Importance of the 5-Hydroxyl Motif for the Inhibition of Aurora Kinases

An efficient protocol for Ru(II)-catalyzed direct C-H oxygenation of a broad range of flavone and chromone substrates was developed. This convenient and powerful synthetic tool allows for the rapid installation of the hydroxyl group into the flavone, chromone, and other related scaffolds and opens the way for analog synthesis of highly potent Aurora kinase inhibitors. The molecular docking simulations indicate that the formation of bidentate H-bonding patterns in the hinge regions between the 5-hydroxyflavonoids and Ala213 was the significant binding force, which is consistent with experimental and computational findings.

Towards the first inhibitors of trihydroxynaphthalene reductase from Curvularia lunata: Synthesis of artificial substrate, homology modelling and initial screening

Trihydroxynaphthalene reductase (3HNR) is an essential enzyme in the biosynthesis of fungal melanin and it represents an emerging target for the development of new fungicides and antimicotics. To promote the discovery of new inhibitors, an improved chemic