3440-24-2

Usage

Uses

Used in Pharmaceutical Industry:
4H-1-Benzopyran-4-one,2-(3,4-dihydroxyphenyl)-7,8-dihydroxyis used as a bioactive compound for its potential anti-inflammatory, anti-cancer, and anti-microbial properties. The presence of multiple hydroxyl groups allows it to interact with various receptors, making it a candidate for the development of new drugs and therapies.
Used in Biomedical Research:
In the field of biomedical research, 4H-1-Benzopyran-4-one,2-(3,4-dihydroxyphenyl)-7,8-dihydroxyis used as a subject of study for understanding its diverse biological activities. Researchers are interested in exploring its potential applications in the treatment of various diseases and conditions, given its chemical properties and interactions with biological systems.
Used in Drug Development:
4H-1-Benzopyran-4-one,2-(3,4-dihydroxyphenyl)-7,8-dihydroxyis used as a lead compound in drug development. Its chemical structure and bioactivity make it a valuable starting point for the synthesis of new drugs with improved efficacy and reduced side effects. 4H-1-Benzopyran-4-one,2-(3,4-dihydroxyphenyl)-7,8-dihydroxy-'s potential as an anti-inflammatory, anti-cancer, or anti-microbial agent is of particular interest to pharmaceutical companies.

Upstream product

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Relevant academic research and scientific papers

Novel synthesised flavone derivatives provide significant insight into the structural features required for enhanced anti-proliferative activity

With many cancers showing resistance to current chemotherapies, the search for novel anti-cancer agents is attracting considerable attention. Natural flavonoids have been identified as useful leads in such programmes. However, since an in-depth understanding of the structural requirements for optimum activity is generally lacking, further research is required before the full potential of flavonoids as anti-proliferative agents can be realised. Herein a broad library of 76 methoxy and hydroxy flavones, and their 4-thio analogues, was constructed and their structure-activity relationships for anti-proliferative activity against the breast cancer cell lines MCF-7 (ER +ve), MCF-7/DX (ER +ve, anthracycline resistant) and MDA-MB-231 (ER -ve) were probed. Within this library, 42 compounds were novel, and all compounds were afforded in good yields and >95% purity. The most promising lead compounds, specifically the novel hydroxy 4-thioflavones 15f and 16f, were further evaluated for their anti-proliferative activities against a broader range of cancer cell lines by the National Cancer Institute (NCI), USA and displayed significant growth inhibition profiles (e.g. compound-15f: MCF-7 (GI50 = 0.18 μM), T-47D (GI50 = 0.03 μM) and MDA-MB-468 (GI50 = 0.47 μM) and compound-16f: MCF-7 (GI50 = 1.46 μM), T-47D (GI50 = 1.27 μM) and MDA-MB-231 (GI50 = 1.81 μM)). Overall, 15f and 16f exhibited 7-46 fold greater anti-proliferative potency than the natural flavone chrysin (2d). A systematic structure-activity relationship study against the breast cancer cell lines highlighted that free hydroxyl groups and the B-ring phenyl groups were essential for enhanced anti-proliferative activities. Substitution of the 4-CO functionality with a 4-CS functionality, and incorporation of electron withdrawing groups at C-4′ of the B-ring phenyl, also enhanced activity. Molecular docking and mechanistic studies suggest that the anti-proliferative effects of flavones 15f and 16f are mediated via ER-independent cleavage of PARP and downregulation of GSK-3β for MCF-7 and MCF-7/DX cell lines. For the MDA-MB-231 cell line, restoration of the wild-type p53 DNA binding activity of mutant p53 tumour suppressor gene was indicated.

Preparation having antioxidant properties

The invention relates to a preparation having antioxidant properties, comprising at least one compound of the formula I where R1 to R10 may be identical or different and are selected from H, OR11, straight-chain or branched C1- to C20-alkyl groups, straight-chain or branched C3- to C20-alkenyl groups, straight-chain or branched C1- to C20-hydroxyalkyl groups, where the hydroxyl group may be bonded to a primary or secondary carbon atom of the chain and furthermore the alkyl chain may also be interrupted by oxygen, and/or C3- to C10-cycloalkyl groups and/or C3- to C12-cycloalkenyl groups, where the rings may each also be bridged by —(CH2)n— groups, where n=1 to 3, where all OR11 are, independently of one another, OH, C1- to C20-alkoxy groups, C3- to C20-alkenyloxy groups, straight-chain or branched C1- to C20-hydroxyalkoxy groups and/or C3- to C10-cycloalkoxy groups and/or C3- to C12-cycloalkenyloxy groups, where the rings may each also be bridged by —(CH2)n— groups, where n=1 to 3, and/or mono- and/or oligoglycosyl radicals, with the proviso that at least 3 radicals from R1 to R7 are OH and that at least 2 pairs of adjacent —OH groups are present in the molecule, or R2, R5 and R6 are OH and the radicals R1, R3, R4 and R7-10 are H.