703-23-1

Usage

Uses

Used in Pharmaceutical Industry:
2'-HYDROXY-6'-METHOXYACETOPHENONE is used as a starting material for the synthesis of aminopyrazole compounds, which are employed as anticancer agents and Chk1 inhibitors. These compounds have shown potential in treating cancer by targeting specific cellular pathways and inhibiting the growth of cancer cells.
Used in Synthesis of 5,7,4'-Disubstituted Flavones:
2'-HYDROXY-6'-METHOXYACETOPHENONE is used as a precursor in the preparation of 5,7,4'-disubstituted flavones, which are predicted to act as androgen receptor antagonists. These compounds have potential applications in the treatment of androgen-dependent conditions and diseases.
Used in Synthesis of Anticancer Agents:
2'-HYDROXY-6'-METHOXYACETOPHENONE is also utilized in the synthesis of naphthopyrazolyl carbothioamides, which are known to possess anticancer properties. These agents target specific cellular mechanisms, contributing to the development of novel cancer therapies.
Used in Synthesis of Flavones:
2'-HYDROXY-6'-METHOXYACETOPHENONE has been used as a starting material in the synthesis of 5-methoxyflavaone and 5,6-dihydroxyflavone. These flavones are known for their diverse biological activities, including antioxidant, anti-inflammatory, and anticancer properties.

Preparation

Preparation by reaction of methyl iodide on 2,6-dihydroxyacetophenone with potassium carbonate in boiling acetone (56%).

InChI:InChI=1/C9H10O3/c1-6(10)9-7(11)4-3-5-8(9)12-2/h3-5,11H,1-2H3

Upstream product

• 186581-53-3 diazomethane 
• 699-83-2 2,6-dihydroxylacetophenone 
• 2040-04-2 2,6-dimethoxyacetophenone 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 211449-28-4 Diethyl-carbamic acid 2-acetyl-3-methoxy-phenyl ester 
• 5451-83-2 acetic acid 3-methoxyphenyl ester 
• 85630-17-7 3-methoxyphenyl N,N-diethylcarbamate 
• 2555-29-5 8-acetyl-7-hydroxy-4-methyl-2H-chromen-2-one 
• 67-56-1 methanol 
• 37514-00-4 2-acetyl-1,3-cyclohexanedione enol 
• 127-19-5 N,N-dimethyl acetamide 
• 217813-03-1 3-methoxy-2-(trimethylsilyl)phenyl-trifluoromethanesulfonate 
• 74-83-9 methyl bromide 

Downstream Products

• 111391-33-4 4-benzyloxy-2'-hydroxy-6'-methoxy-trans-chalcone 
• 412022-08-3 3-acetyl-2-hydroxy-4-methoxy-benzaldehyde 
• 109469-61-6 2'-hydroxy-6'-methoxy-2-methoxymethoxy-trans-chalcone 
• 110048-25-4 2'-hydroxy-3,6'-dimethoxy-2-methoxymethoxy-trans-chalcone 
• 103440-57-9 1-(2-hydroxy-3-iodo-6-methoxy-phenyl)-ethanone 
• 33539-20-7 6-methoxy-2,5-dihydroxyacetophenone 
• 38226-01-6 1-(2-hydroxy-6-methoxy-3-nitro-phenyl)-ethanone 
• 37113-62-5 1-(3-bromo-2-hydroxy-6-methoxy-phenyl)-ethanone 
• 3147-64-6 2-hydroxy-6-methoxybenzoic acid 
• 98954-40-6 2-ethyl-3-methoxyphenol 
• 109341-92-6 1-(2-hydroxy-3,5-diiodo-6-methoxy-phenyl)-ethanone 
• 109589-33-5 (E)-1-(2-hydroxy-6-methoxyphenyl)-3-(3,4-methylenedioxy-phenyl)prop-2-en-1-one 
• 103154-01-4 bis-(3-acetyl-2-hydroxy-4-methoxy-phenyl)-sulfide 
• 135831-50-4 2-acetyl-3-methoxyphenyl acetate 

Relevant academic research and scientific papers

Unraveling the anti-influenza effect of flavonoids: Experimental validation of luteolin and its congeners as potent influenza endonuclease inhibitors

The biological effects of flavonoids on mammal cells are diverse, ranging from scavenging free radicals and anti-cancer activity to anti-influenza activity. Despite appreciable effort to understand the anti-influenza activity of flavonoids, there is no clear consensus about their precise mode-of-action at a cellular level. Here, we report the development and validation of a screening assay based on AlphaScreen technology and illustrate its application for determination of the inhibitory potency of a large set of polyols against PA N-terminal domain (PA-Nter) of influenza RNA-dependent RNA polymerase featuring endonuclease activity. The most potent inhibitors we identified were luteolin with an IC50 of 72 ± 2 nM and its 8-C-glucoside orientin with an IC50 of 43 ± 2 nM. Submicromolar inhibitors were also evaluated by an in vitro endonuclease activity assay using single-stranded DNA, and the results were in full agreement with data from the competitive AlphaScreen assay. Using X-ray crystallography, we analyzed structures of the PA-Nter in complex with luteolin at 2.0 ? resolution and quambalarine B at 2.5 ? resolution, which clearly revealed the binding pose of these polyols coordinated to two manganese ions in the endonuclease active site. Using two distinct assays along with the structural work, we have presumably identified and characterized the molecular mode-of-action of flavonoids in influenza-infected cells.

With 5, 2 '- dihydroxy -4' - methoxy -3 - geranyl flavone skeleton derivative and its preparation and use

The invention discloses a derivative with a 5,2'-dihydroxy-4'-methoxy-3-geranyl flavone skeleton. The derivative has a chemical general formula (1) shown in the description or pharmaceutically acceptable salts thereof, wherein R is a formula shown in the description or a formula shown in the description, R1 is -OCH3 or -OH, R2 is -OCH3 or -OH, and R3 is -OCH3 or -OH. The derivative disclosed by the invention has good cervical carcinoma and hepatic carcinoma resisting activity, has multiple target points, multiple links and multiple correspondence, is low in toxicity and is not prone to drug resistance generation.

With 5, 2 '- dihydroxy - 4' - methoxy - 3 - geranyl flavone skeleton derivative and its preparation and use

The invention discloses a derivative with a 5,2'-dihydroxy-4'-methoxy-3-geranylated flavone framework and a preparation method for the derivative and use of the derivative. The derivative is represented by the chemical general formula (I) or is pharmaceutically acceptable salts thereof: the formula (I) is shown in the description, wherein R1 represents -OCH3 or -OH, R2 is -Cl or -Br, R3 is -OCH3 or -OH, and R4 is -OCH3 or -OH. The obtained derivative has good cervical cancer resisting activity, has multiple target points, multiple links and multiple effects, is low in toxicity and is not easy to cause drug resistance.

Synthesis and bioevaluation of substituted chalcones, coumaranones and other flavonoids as anti-HIV agents

A series of chalcone, flavone, coumaranone and other flavonoid compounds were screened for their anti HIV-1 activity in two cell culture models using TZM-bl and PM1 cells. Within the systems evaluated, the most promising compounds contained either an α- or β-hydroxy-carbonyl motif within their structure (e.g., 8 and 9). Efficacious substituents were identified and used to design new HIV inhibitors with increased potency and lower cytotoxicity. Of the scaffolds evaluated, specific chalcones were found to provide the best balance between anti-HIV potency and low host cell toxicity. Chalcone 8l was shown to inhibit different clinical isolates of HIV in a dose-dependent manner (e.g., IC50 typically ≤ 5 μM). Inhibition of HIV infection experiments using TZM-bl cells demonstrated that chalcone 8l and flavonol 9c had IC50 values of 4.7 μM and 10.4 μM, respectively. These insights were used to design new chalcones 8o and 8p. Rewardingly, chalcones 8o and 8p (at 10 μM) each gave >92% inhibition of viral propagation without impacting PM1 host cell viability. Inhibition of viral propagation significantly increased (60-90%) when PM1 cells were pre-incubated with chalcone 8o, but not with the related flavonol 9c. These results suggested that chalcone 8o may be of value as both a HIV prophylactic and therapy. In summary, O-benzyl-substituted chalcones were identified as promising anti-HIV agents for future investigation.

The synthesis and synergistic antifungal effects of chalcones against drug resistant Candida albicans

To identify effective and low toxicity synergistic antifungal compounds, 24 derivatives of chalcone were synthesized to restore the effectiveness of fluconazole against fluconazole-resistant Candida albicans. The minimal inhibitory concentration (MIC80) and the fractional inhibitory concentration index (FICI) of the antifungal synergist fluconazole were measured against fluconazole-resistant Candida albicans. This was done via methods established by the clinical and laboratory standards institute (CLSI). Of the synthesized compounds, 2′-hydroxy-4′-methoxychalcone (8) exhibited the most potent in vitro (FICI = 0.007) effects. The structure activity relationship of the compounds are then discussed.

Natural product analogues Rubraflavone A and its preparation method and application

The invention discloses natural product Rubraflavone A analogues as well as a preparation method and an application thereof. On the basis of a natural product Rubraflavone A, a series of natural product Rubraflavone A analogues with flavonoid compound skeleton structures are researched and prepared by the inventor, and the total synthesis of the analogues and the in-depth study on the anti-gastric cancer cell activity of the analogues are carried out. The test on the in-vitro cancer cell inhibitory activity shows that target compounds 6a, 6b, 7a1, 7b1 and 7b2 disclosed by the invention have obvious inhibitory effects on gastric cancer cell strains (SGC-7901) and can be used as medicines for treating gastric cancers.

Novel chromone and xanthone derivatives: Synthesis and ROS/RNS scavenging activities

Chromones and xanthones are oxygen-containing heterocyclic compounds acknowledged by their antioxidant properties. In an effort to develop novel agents with improved activity, a series of compounds belonging to these chemical classes were prepared. Their syntheses involve the condensation of appropriate 2-methyl-4H-chromen-4-ones, obtained via Baker-Venkataraman rearrangement, with (E)-3-(3,4-dimethoxyphenyl)acrylaldehyde to provide the corresponding 2-[(1E,3E)-4-(3,4-dimethoxyphenyl)buta-1,3-dien-1-yl]-4H-chromen-4-ones. Subsequent electrocyclization and oxidation of these compounds led to the synthesis of 1-aryl-9H-xanthen-9-ones. After cleavage of the protecting groups, hydroxylated chromones and xanthones were assessed as scavenging agents against both reactive oxygen species (ROS) [superoxide radical (O2?-), hydrogen peroxide (H2O2), hypochlorous acid (HOCl), singlet oxygen (1O2), and peroxyl radical (ROO?)] and reactive nitrogen species (RNS) [nitric oxide (?NO) and peroxynitrite anion (ONOO-)]. Generally, all the tested new hydroxylated chromones and xanthones exhibited scavenger effects dependent on the concentration, with IC50 values found in the micromolar range. Some of them were shown to have improved scavenging activity when compared with previously reported analogues, allowing the inference of preliminary conclusions on the structure-activity relationship.

Flavonoid derivatives as selective ABCC1 modulators: Synthesis and functional characterization

A series of chromones, bearing substituted amino groups or N-substituted carboxamide moieties in position 2, was synthesized and characterized in cellular assays for modulation of the ABC transporters ABCC1 (MDCKII-MRP1 cells), ABCB1 (Kb-V1 cells) and ABCG2 (MCF-7/Topo cells). The most potent ABCC1 modulators identified among these flavonoid-type compounds were comparable to the reference compound reversan regarding potency, but superior in terms of selectivity concerning ABCB1 and ABCG2 (2-[4-(Benzo[c][1,2,5]oxadiazol-5-ylmethyl)piperazin-1-yl]-5,7-dimethoxy-4H-chromen-4-one (51): ABCC1, IC50 11.3-1/4M; inactive at ABCB1 and ABCG2). Compound 51 was as effective as reversan in reverting ABCC1-mediated resistance to cytostatics in MDCKII-MRP1 cells and proved to be stable in mouse plasma and cell culture medium. Modulators, such as compound 51, are of potential value as pharmacological tools for the investigation of the (patho)physiological role of ABCC1.

Synthesis, biological evaluation, and molecular simulation of chalcones and aurones as selective MAO-B inhibitors

A series of chalcones and aurones were synthesized and evaluated in vitro as monoamine oxidase inhibitors (MAOi). Our results show that aurones, which had not been previously reported as MAOi, are MAO-B inhibitors. Thus, both families inhibited selectively the B isoform of MAO in the micromolar range, offering novel scaffolds for the design of new and potent MAO inhibitors. The main structural requirements for their activity were characterized with the aid of 3D-QSAR and docking studies.

Lithiation of a silyl ether: Formation of an ortho-fries hydroxyketone

A hydroxy-directed alkylation of an N,N-diethylarylamide using CIPE-assisted α-silyl carbanions (CIPE=complex-induced proximity effect) has been developed using a simple reagent combination of LDA (lithium diisopropylamide) and chlorosilane. A study of the mechanism, and the application of the procedure to an anionic Snieckus-Fries rearrangement for a highly efficient synthesis of the potent phosphatidylinositol 3-kinase (PI3K) inhibitor LY294002, are reported.