22395-22-8

Usage

benefits

7-methoxyflavone is popular nowadays as one of the most powerful aromatase inhibitor and testosterone booster. It is isolated from Zornia brasiliensis. It might change how the body breaks down chemicals called hormones. Some people think this might cause the body to have more of the hormone called testosterone. Testosterone can help build muscle, but can also cause serious side effects.

Biological Activity

7-Methoxyflavone is a flavone that has been found in Z. brasiliensis and has diverse biological activities. It inhibits aromatase (IC50 = 1.9 μM in a cell-free assay) and LPS-induced nitric oxide (NO) production by 17.74% in RAW 264.7 macrophages when used at a concentration of 20 μM. 7-Methoxyflavone activates androgen and/or glucocorticoid receptor transcriptional activity in a reporter assay and has antinociceptive effects in the acetic acid-induced writhing test in mice (ED50 = 82.5 μmol/kg).

InChI:InChI=1/C16H14O3/c1-18-12-7-8-13-14(17)10-15(19-16(13)9-12)11-5-3-2-4-6-11/h2-9,15H,10H2,1H3

Upstream product

• 56-23-5 tetrachloromethane 
• 128-08-5 N-Bromosuccinimide 
• 21785-09-1 7-methoxyflavanone 
• 94-36-0 dibenzoyl peroxide 
• 6665-86-7 7-hydroxyflavone 
• 74-88-4 methyl iodide 
• 52752-67-7 1-(2-hydroxy-4-methoxyphenyl)-3-phenylpropane-1,3-dione 
• 22141-31-7 4’-methoxy-2’-hydroxyl-dihydrochalcone 
• 546-67-8 lead(IV) tetraacetate 
• 64-19-7 acetic acid 
• 109650-29-5 3-benzoyl-4-hydroxy-7-methoxycoumarin 
• 80370-26-9 1-(2,4-dimethoxyphenyl)-3-phenyl-1,3-propanedione 
• 124260-01-1 benzoic acid 2-acetyl-5-methoxyphenyl ester 
• 39273-61-5 (E)-1-(2-hydroxy-4-methoxyphenyl)-3-phenylprop-2-en-1-one 

Downstream Products

• 244107-94-6 7-methoxy-2-phenyl-chromene-4-thione 
• 153936-30-2 4-(p-benzyloxyphenyl)-4-hydroxy-7-methoxy-2-phenyl-4H-chromene 
• 128814-92-6 5-Methoxy-7a-phenyl-1a,7a-dihydro-1H-7-oxa-cyclopropa[b]naphthalen-2-one 
• 22141-31-7 4’-methoxy-2’-hydroxyl-dihydrochalcone 
• 136764-58-4 1a,7a-Dihydro-4-methoxy-1a-phenyl-7H-oxireno<1>benzopyran-7-one 
• 153446-72-1 3-iodo-7-methoxy-2-phenyl-4H-chromen-4-one 
• 6665-86-7 7-hydroxyflavone 
• 66715-20-6 7-methoxy-2-phenyl-4H-1-benzopyran 
• 907547-83-5 4-(2-hydroxy-4-methoxyphenyl)-6-phenyl-2-aminopyrimidine 
• 42345-25-5 7-hydroxy-4-oxo-2-phenyl-4H-chromene-8-carbaldehyde 
• 63790-45-4 7-methoxy-4-oxo-2-phenyl-4H-chromene-8-carbaldehyde 

Relevant academic research and scientific papers

Divergent synthesis of flavones and flavanones from 2′-hydroxydihydrochalconesviapalladium(ii)-catalyzed oxidative cyclization

Divergent and versatile synthetic routes to flavones and flavanonesviaefficient Pd(ii) catalysis are disclosed. These Pd(ii) catalyses expediently provide a variety of flavones and flavanones from 2′-hydroxydihydrochalcones as common intermediates, depending on oxidants and additives,viadiscriminate oxidative cyclization sequences involving dehydrogenation, respectively, in a highly atom-economic manner.

A novel one-pot synthesis of flavones

In this paper, a one-pot facile route for the BiCl3/RuCl3-mediated synthesis of functionalized flavones is described, including: (i) intermolecularortho-acylation of substituted phenols with cinnamoyl chlorides, and (ii) intramolecular cyclodehydrogenation of the resultingo-hydroxychalcones. The reaction conditions are discussed herein.

Biocatalytic green alternative to existing hazardous reaction media: Synthesis of chalcone and flavone derivatives via the Claisen-Schmidt reaction at room temperature

Owing to the increasing amount of waste materials around the globe, the conversion of waste or secondary by-products to value-added products for various applications has gained significant interest. Herein, two novel agro-food waste products, Musa sp. 'Malbhog' peel ash (MMPA) and Musa Champa Hort. ex Hook. F. peel ash (MCPA) are used as catalysts to promote an inexpensive, efficient and eco-friendly carbon-carbon bond forming crossed aldol reaction at room temperature in solvent free conditions. Furthermore, the resulting products were subjected to reactions with these promoters in an oxygen atmosphere and led to the formation of novel flavone derivatives. Moreover, the used catalysts were properly characterized using different sophisticated analytical techniques such as Fourier-transform infrared spectroscopy (FT-IR), X-ray diffractometry (XRD), Brunauer-Emmett-Teller analysis (BET), Raman spectroscopy, scanning electron microscopy energy dispersive X-ray spectroscopy (SEM-EDS), transition electron microscopy (TEM), X-ray photoelectron spectroscopy (XPS) and thermogravimetric analysis (TGA) along with element detection using atomic absorption spectroscopy and ion chromatographic methods. These two approaches are metal free, as well as being devoid of any extra additives, co-catalysts, harsh conditions, the use of column chromatography for purification and result in a higher yield of the product within a short space of time. The catalytic abilities of the promoter were also examined to synthesize important bioactive molecules such as butein and apigenin at room temperature. With gram scale synthesis of the chalcone derivatives, the used catalysts (MMPA and MCPA) were further reused for five cycles and did not demonstrate any loss in catalytic activity.

Method for synthesizing 2-aryl benzopyrone flavonoid derivatives

The invention relates to a method for synthesizing 2-aryl benzopyrone flavonoid derivatives, and relates to a method for synthesizing a compound, the method for synthesizing 2-aryl benzopyrone flavonoid derivatives is suitable for the synthesis of 2-aryl benzopyrone flavonoid derivatives containing different substituents. The method aims to solve the technical problems of low yield, long reactionperiod, and complicated post-treatment and high operation difficulty of the existing synthesis method of the ketone flavonoid derivative. The method comprises the following steps of: 1, preparing beta-propanedione compounds; 2, preparing flavonoid compound 2-aryl benzopyranones. The method completes esterification and rearrangement in one step, which is simple and practical, reduces intermediate links of reaction, saves separation and purification of intermediate products, improves utilization rate of raw materials, reduces reaction temperature, shortens reaction time under microwave radiation, reduces solvent consumption, the post-treatment is relatively simple, the yield is relatively high and no by-products exist, and can also react in the presence of a small amount of water, the reaction is easy to operate, and the method is suitable for industrial production. The method belongs to the technical field of compound synthesis.

Microwave assisted efficient synthesis of flavone using ZnO nanoparticles as promoter under solvent-free conditions

A simple and highly efficient protocol for synthesis of flavones from 1-(2-hydroxyphenyl)-3-aryl-1,3-propanediones in presence of ZnO nanoparticles as a promoter in thermal as well as microwave irradiation under solvent-free conditions have been demonstrated. The catalyst is inexpensive, stable, can be easily recycled/reused for several cycles with consistent activity and observed almost same yield confirming the stability of the catalyst. It is believed that the present approach will become an alternative route for the conventional reactions. Because in this protocol, yield is quite high, short reaction time, simple work up, catalyst can be recycled as well as it is free of any hazardous by-products formation during workup.

One Pot Synthesis of γ-Benzopyranones via Iron-Catalyzed Aerobic Oxidation and Subsequent 4-Dimethylaminopyridine Catalyzed 6-endo Cyclization

One-pot synthesis of γ-benzopyranones was realized in decent yields and excellent regioselectivities via iron-catalyzed aerobic oxidation and 4-dimethylaminopyridine-catalyzed cyclization of related propargylic alcohols. Derivatizations to aromatic substituted γ-benzopyranones and synthesis of naturally occurring 3′,4′-dimethoxyflavone have also been realized. (Figure presented.).

Synthesis, antiproliferative and pro-apoptotic effects of nitrostyrenes and related compounds in Burkitt’s lymphoma

Background: Cancers of the lymphatic cells (lymphomas) account for approximately 12% of malignant diseases worldwide. The nitrostyrene scaffold is identified as a lead target structure for the development of particularly effective compounds targeting Burkitt’s lymphoma (BL). Objectives: The aims of the curent study were to synthesise a panel of nitrostyrene compounds and to evaluate their activity in Burkitt’s lymphoma (BL). Methods: A panel of structurally varied compounds were designed and synthesised using Henry Knoevenagel condensation reactions. Single crystal X-Ray analysis confirmed the E configuration for six examples of these novel structures. A number of nitrostyrene-related compounds were also investigated including 1,3-bis(aryl)-2-nitropropenes together with heterocyclic scaffolds containing the nitrovinyl pharmacophore such as 3-nitro-2-phenyl-2H-chromenes. The antiproliferative activities of the compounds were evaluated using the BL cell lines EBV- MUTU-1 and EBV+ DG-75 (chemoresistant) to establish preliminary structure-activity relationships. Results: Lead compounds with optimized nitrostyrene scaffolds and 3-nitro-2-phenyl-2Hchromene structures were successfully established with typical IC50 values of 0.45 μM and 0.47 μM in MUTU-1 cells and 1.41 μM and 1.92 μM, respectively, in DG-75 cells. The mechanism of cell death was identified as apoptotic and the lead compound was found to elicit comparable apoptotic effects to Taxol in Burkitt’s lymphoma cell lines MUTU-1 and DG-75. Conclusion: This class of pharmaceutically active compounds with potential for the treatment of Burkitt’s lymphoma suggest a potential role for nitrostyrene based agents in chemotherapy.

Rational design for multicolor flavone-based fluorophores with aggregation-induced emission enhancement characteristics and applications in mitochondria-imaging

Fluorophores with aggregation-induced emission enhancement (AIEE) properties have attracted more attention in recent years. In order to realise more valuable applications, the different kinds of AIEE molecules are in serious need of further development. Therefore, a novel flavone-based AIEE system derived from restriction of intramolecular rotation (RIR) was designed and synthesized in this work. The results revealed that six of the compounds showed typical AIEE characteristics, with fluorescence emissions from purple, blue, cyan to green, tunable by changing substituent groups. This flavone-based AIEE system has never been reported before. The AIEE characteristics were investigated by optical spectroscopy, fluorescence photographs, scanning electron microscopy (SEM), fluorescence quantum yields (φF) and fluorescence lifetime in the CH3OH/H2O mixed solution. Moreover, benefiting from the simple structures and small molecular weight, they could permeate cells faster than current high-molecular-weight AIEE molecules. Furthermore, to examine possible biomedical applications, fluorescence imaging in living A549 lung cells and cell viabilities were examined, and the results displayed that these fluorophores showed good cellular uptake and low cytotoxicity within the experimental concentration range. In addition, these AIEE compounds possessed excellent specificity for mitochondrial targeting and mitochondrial morphological change tracking, besides, they displayed superior photostability, which indicated they are potential candidates for mitochondrial imaging.

Green and efficient synthesis of flavones and chromones using heteropolyacids as catalyst in glycerol

Organic solvents are required to carry out most organic transformations, which cause environmental pollution because of their low volatility. Glycerol, a side product obtained from biodiesel production, has emerged as a friendly solvent due to its advantageous properties. In this paper, an efficient procedure for the synthesis of flavones and chromones, using heteropolyacids as recyclable catalyst and glycerol as the solvent, is presented. The use of heteropolyacids as catalysts allows for excellent yields, easy separation and recovery, low environmental impact, and low cost. Glycerol can also be readily recovered and used over again. In addition, the presented method provides other advantages such as the low formation of waste and the replacement of corrosive mineral acids.

One-Pot Allan–Robinson/Friedl?nder Route to Chromen-/Quinolin-4-ones through the Domino Acetylative Cyclisation of 2-Hydroxy-/2-Aminobenzaldehydes

The domino synthesis of 2-phenyl-4H-chromen-4-ones and quinolin-4-ones through acetylation of 2-hydroxy-/2-aminobenzaldehydes with α-haloketones followed by intramolecular oxa-/azaheterocyclisation is reported. This method represents a new extension of the Allan–Robinson and Friedl?nder reactions, and uses N-heterocyclic-carbene catalysis to construct the target molecules in good to excellent yields: 86–95 % for the chromen-4-ones, and 83–96 % for the quinolin-4-ones. This approach has the advantages of operational simplicity, ambient reaction conditions, and no by-product formation.