6320-42-9

Usage

Uses

Used in Pharmaceutical Industry:
7-Hydroxy-2-methyl-4H-chromen-4-one is used as an intermediate in the synthesis of various pharmaceutical compounds, such as 2,2-Dimethyl-2H-pyranoflavonol and pyranochromone derivatives. These synthesized compounds have potential applications in the development of new drugs with therapeutic properties.
Used in Chemical Synthesis:
7-Hydroxy-2-methyl-4H-chromen-4-one serves as a key building block in the synthesis of a wide range of organic compounds, including flavonoids, chromones, and other heterocyclic compounds. Its unique structure allows for various chemical reactions, making it a valuable component in the synthesis of complex organic molecules.
Used in Research and Development:
7-hydroxy-2-methyl-4H-chromen-4-one is also used in research and development for studying its biological activities and potential applications. Researchers can use 7-hydroxy-2-methyl-4H-chromen-4-one to investigate its interactions with biological systems, such as enzymes, receptors, and cellular pathways, to better understand its therapeutic potential and develop new drugs based on its structure and properties.

InChI:InChI=1/C10H8O3/c1-6-4-9(12)8-3-2-7(11)5-10(8)13-6/h2-5,11H,1H3

Upstream product

• 78812-99-4 Acetic acid 2-(1-acetoxy-vinyl)-5-hydroxy-phenyl ester 
• 107127-91-3 [2-(2,4-Bis-benzoyloxy-phenyl)-2-oxo-ethyl]-triphenyl-phosphonium; bromide 
• 83526-81-2 7-acetoxy-2-methyl-chromen-4-one 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 75-36-5 acetyl chloride 
• 123253-31-6 1<2-hydroxy-4-(2'-methoxyethoxy)methoxyphenyl>-1-ethanone 
• 42528-99-4 2,4’-diacetoxyacetophenone 
• 5706-85-4 2-hydroxy-1-(4-hydroxyphenyl)ethan-1-one 
• 141-78-6 ethyl acetate 
• 108-46-3 recorcinol 
• 258856-60-9 2',4'-dibenzoyloxy-2-bromoacetophenone 
• 66832-97-1 2,4-dibenzoyloxyacetophenone 
• 72712-19-7 2,4-diacetoxy acetophenone 
• 34128-24-0 1-(4-benzyloxy-2-hydroxyphenyl)-1,3-butanedione 

Downstream Products

• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 89-86-1 4-hydroxysalicylic acid 
• 64-19-7 acetic acid 
• 105197-64-6 8-benzoyl-7-hydroxy-2-methylchromone 
• 101350-00-9 2-hydroxy-3-iodo-4-methoxy-benzoic acid 
• 98554-58-6 2,5-dihydroxy-3-iodo-4-methoxy-benzoic acid 
• 98558-03-3 2-hydroxy-3,5-diiodo-4-methoxy-benzoic acid 
• 113495-11-7 C₂₀H₁₉N₃O₅S 
• 113495-10-6 C₁₉H₁₆ClN₃O₄S 
• 113495-09-3 C₂₀H₁₉N₃O₄S 
• 113495-08-2 C₁₉H₁₇N₃O₄S 
• 22604-84-8 2,4-dihydroxy-3,5-dinitro-benzoic acid 
• 54917-82-7 2,4-dihydroxy-3,5-dinitroacetophenone 
• 101277-65-0 7-hydroxy-2-methyl-chromen-4-one-(2,4-dinitro-phenylhydrazone) 

Relevant academic research and scientific papers

Biological activity evaluation and molecular docking study of chromone derivatives as cyclooxygenase-2 inhibitors

A series of chromone derivatives have been evaluated as potential cyclooxygenase-2 (COX-2) inhibitors. The four most potent compounds, 48, 41, 39, and 35 displayed IC50 values of 3.30, 6.86, 7.36 and 7.46 μM, respectively. Compounds 35 and 38 showed higher selectivity for COX-2 (selectivity index, SI = 7.48 and 5.46, respectively) than celecoxib (SI = 4.17 in the same test) whereas compound 39 showed comparable selectivity (SI = 4.19) to celecoxib. The molecular volumes of compounds 35 (312.84 ?3) and 38 (314.18 ?3) were similar to celecoxib (299.28 ?3) but larger than ibuprofen (211.83 ?3). Docking results were in good agreement with the experimental biological data in terms of evaluation of binding energy and binding mode. Compounds 35, 38, and 39 had higher binding affinity against COX-2 (binding energy between ?9.77 and ?11.42 kcal/mole) than COX-1 (binding energy between ?6.28 and ?7.88 kcal/mole). These three chromone compounds also displayed active conformation in the same orientation as that of celecoxib. Thus, compounds in this series has the potential to be a new class of selective COX-2 inhibitor.

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.

Development of 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs) from natural isoflavones, a new class of fluorescent scaffolds for biological imaging

Starting from 7-hydroxyisoflavones, we developed a new class of fluorescent scaffolds, 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs, MW ～ 205.19, λab ～ 350 nm, λem ～ 450 nm) via a trial and error process. AMHCs have the advantages of being a small molecular moiety, having strong fluorescence in basic buffers, reasonable solubility and stability, non-toxicity, and are conveniently linked to pharmacophores. AMHCs were successfully used in fluorescence microscopy imaging of cells and tissues. This journal is

Anti-AIDS agents 89. Identification of DCX derivatives as anti-HIV and chemosensitizing dual function agents to overcome P-gp-mediated drug resistance for AIDS therapy

In this study, 19 dicamphanoyl-dihydropyranochromone (DCP) and dicamphanoyl-dihydropyranoxanthone (DCX) derivatives, previously discovered as novel anti-HIV agents, were evaluated for their potential to reverse multi-drug resistance (MDR) in a cancer cell line over-expressing P-glycoprotein (P-gp). Seven compounds fully reversed resistance to vincristine (VCR) at 4 μM, a 20-fold enhancement compared to the first generation chemosensitizer, verapamil (4 μM). The mechanism of action of DCPs and DCXs was also resolved, since the most active compounds (3, 4, and 7) significantly increased intracellular drug accumulation due, in part, to inhibiting the P-gp mediated drug efflux from cells. We conclude that DCPs (3 and 4) and DCXs (7, 11, and 17) can exhibit polypharmacologic behavior by acting as dual inhibitors of HIV replication and chemoresistance mediated by P-gp. As such, they may be useful in combination therapy to overcome P-gp-associated drug resistance for AIDS treatment.

Synthesis, in vitro evaluation, and docking studies of novel chromone derivatives as HIV-1 protease inhibitor

Novel chromone derivatives with a benzopyran-4-one scaffold have been prepared by the one-pot cyclization reaction. The in vitro inhibitory activity of these new compounds towards HIV-1 protease have been evaluated using stop time HPLC method as the preliminary screening. The most potent compound, 7,8-dihydroxy-2-(3′-trifluoromethyl phenyl)-3-(3″- trifluoromethylbenzoyl)chromone (32), showed IC50 = 0.34 μM. The molecular docking study supported results from experimental activity testing and also provided structure-activity relationship of this series.

Anti-AIDS agents. 60. Substituted 3′R,4′R-di-O-(-)-camphanoyl- 2′,2′-dimethyldihydropyrano[2,3-f]chromone (DCP) analogues as potent anti-HIV agents

Synthesis of positional isomers is a commonly used technique in drug design. Accordingly, based on prior SAR studies of 3′R,4′R-di-O-(S)- camphanoyl-(+)-cis-khellactone (DCK, 1) analogues, a series of mono- and disubstituted chromone derivatives of 3′R,4′R-di-O-(-)camphanoyl- 2′,2′-dimethyldihydropyrano[2,3-f]chromone (DCP, 4) were designed and synthesized. Together with 1 and 4-methyl DCK (2), all newly synthesized DCP analogues (4-21) were screened for anti-HIV-1 activity against a non-drug-resistant strain in H9 lymphocytes and a multiple reverse transcriptase (RT) inhibitor-resistant strain in the MT4 cell line. Several DCP analogues (4, 5, 7, 8, 13, and 17) exhibited extremely high anti-HIV activity in the nondrug-resistant strain assay, with EC50 values ranging from 0.00032 to 0.0057 μM and remarkable therapeutic indexes (TI) ranging from 5.6 × 103 to 1.16 × 105, which were similar to those of 2 (EC50 0.0059 μM, TI > 6.6 × 103) and better than those of 1 (EC50 0.049 μM, TI > 328). Even more promisingly, some DCP analogues also showed activity against a multi-RT inhibitor-resistant strain, HIV-1 RTMDR1, whereas most DCK analogues did not. The most significant compound was 8, with an EC50 value of 0.06 μM and TI of 718 against the multi-RT inhibitor-resistant HIV-1 strain. Compounds 9 and 10 also showed good activity with an EC50 value of 0.14 μM, and TIs of 272 and >111, respectively. 2-Ethyl DCP (8) exhibited the best anti-HIV activity in both assays. Further development of 8-related compounds as clinical trial candidates is warranted.

Flavonoids, 45 . A General and Efficient Synthesis of Hydroxyflavones and -chromones

An efficient and versatile method for the synthesis of flavones hydroxylated in either ring A or B and of chromones hydroxylated in is described.This approach is based on the acidic resin-promoted cyclodehydration and simultaneous deprotection of methoxymethoxylated 1-(2-hydroxyphenyl)propane-1,3-diones easily available by either the Baker-Venkataraman rearrangement or the Claisen condensation. - Key words: Amberlyst 15 / Baker-Venkataraman rearrangement / Claisen condensation / hydroxychromone / hydroxyflavone / methoxymethyl protection

SYNTHESE DE DIHYDROXY PHENACYLIDENE TRIPHENYLPHOSPHORANES NOUVEAUX PRECURSEURS DE COMPOSES FLAVONOIDES : SYNTHESE D'HYDROXY-6 ET HYDROXY-7 CHROMONES.

The synthesis of two new dihydroxy phenacylidene triphenylphosphoranes from 2,4-dibenzoyloxy and 2,5-dibenzoyloxy acetophenones is described.By acylation of the hydroxyl groups of these ylides, intramolecular olefination of the ester carbonyl group and hydrolysis of the second ester group, some 6-hydroxy and 7-hydroxy chromones are prepared with good yields.

Photolysis of Enol Acetates and α-Bromo Derivatives of o-(Acyloxy)acetophenones

UV irradiation of enol acetates 3a-g in benzene gives mainly o-(acetoxy)acetophenones 2 and 2-methylchromones 4. Under the same conditions, the dimethyl derivatives 3h and 3i remain unaffected.The α-bromo ketone 5a gives rise to mixtures of o-(acetoxy)acetophenone (2a), the diketone 6, and/or α-acetoxy-o-hydroxyacetophenone (7), depending on the irradiation conditions.The similarities and differences between the two series of experiments, as well as their possible mechanistic implications, are discussed.

Biosynthesis of Aspyrone, a Metabolite of Aspergillus melleus. Incorporation Studies with 14C- and 3H-Labelled Acetates and Malonate

Incorporation studies with 14C-labelled acetates and malonate confirm the polyketide origin of aspyrone (1), and identify the chain starter unit.Five carbons are derived from the methyl group of acetate, and the remaining four from the carboxy group.The pattern of incorporation of tritium from acetate is inconsistent with a biosynthesis from aromatic precursors of the mellein type.Possibly advanced precursors containing a 2-methylchromone nucleus were not incorporated.The evidence suggests that aromatic precursors are not involved in aspyrone biosynthesis, and that the carbon skeleton is produced like that of the co-metabolite asperlactone (6), by decarboxylation and rearrangement of a linear pentaketide intermediate.