33507-94-7

Upstream product

• 33495-30-6 2-benzoyloxy-4,6-dimethoxyacetophenone 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 98-88-4 benzoyl chloride 
• 93-89-0 benzoic acid ethyl ester 
• 65-85-0 benzoic acid 
• 480-66-0 2,4,6-trihydroxyacetophenone 

Downstream Products

• 21392-57-4 Dimethyl-chrysin 
• 124259-94-5 3,5-dimethoxy-2-(5-phenyl-1⁽²⁾H-pyrazol-3-yl)-phenol 
• 124259-97-8 2-[1-(2,4-Dinitro-phenyl)-5-phenyl-1H-pyrazol-3-yl]-3,5-dimethoxy-phenol 
• 124259-96-7 3,5-Dimethoxy-2-(5-phenyl-1-p-tolyl-1H-pyrazol-3-yl)-phenol 
• 41988-26-5 7-(2-bromoethoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one 
• 1190373-61-5 5-hydroxy-2-phenyl-7-(2-(piperazin-1-yl)ethoxy)-4H-chromen-4-one 
• 1190373-62-6 7-(2-(diethylamino)ethoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one 
• 1190373-63-7 7-(2-(propylamino)ethoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one 
• 1190373-64-8 7-(2-(dipropylamino)ethoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one 
• 1190373-65-9 5-hydroxy-7-(2-(4-methylpiperazin-1-yl)ethoxy)-2-phenyl-4H-chromen-4-one 
• 1190373-66-0 7-(2-(dibutylamino)ethoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one 
• 1190373-67-1 5-hydroxy-2-phenyl-7-(2-(pyrrolidin-1-yl)ethoxy)-4H-chromen-4-one 
• 1190373-69-3 5-hydroxy-2-phenyl-7-(2-(piperidin-1-yl)ethoxy)-4H-chromen-4-one 
• 1236122-77-2 7-(2-(isopropylamino)ethoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one 

Relevant academic research and scientific papers

One-pot synthesis of 3-fluoroflavones: Via 1-(2-hydroxyphenyl)-3-phenylpropane-1,3-diones and selectfluor at room temperature

A concise and efficient one-pot strategy to synthesize 3-fluoroflavones was developed. 1-(2-Hydroxyphenyl)-3-phenylpropane-1,3-diones were fluorinated using selectfluor with a small amount of CH3CN at room temperature, followed by cyclization a

Mild and efficient organocatalytic method for the synthesis of flavones

A convenient and efficient organocatalytic procedure for the selective cyclization of 1,3-diketones to give aromatic substituted 4H-chromen-4-ones under mild reaction conditions using N-triflyl phosphoramide is described. Application of the described conditions is presented in a formal synthesis of (S)-flavanone.

One-Pot Synthesis of Benzopyran-4-ones with Cancer Preventive and Therapeutic Potential

A one-pot synthesis of novel benzopyran-4-ones is described. In a tandem reaction, organobase-catalysed Michael addition of R1COCH2COR2 on chromone-3-carboxylic acid led to decarboxylation and pyran-4-one ring opening of the latter. This was followed by chromone-and/or chromanone ring closure of the resulting Michael adducts when R1 is an ortho-hydroxyaryl group. Antioxidant testing of 14 derivatives identified strong antiradical properties of chromanones 3o-r (2.1-3.1 μmol Trolox equiv./μmol compound in the DPPH assay). Chromanones 3p and 3r and 2-styrylchromone 3k were also most potent in inducing the cytoprotective Keap1-Nrf2 signalling pathway in a reporter gene assay (fivefold induction at concentrations 3 μM). Of the seven compounds evaluated for antiproliferative activities, 3k and 3r were the most active, inhibiting leukaemia K562 cell proliferation by 50 % after 72 h at concentrations of 4.5 and 7.9 μM, whereas normal peripheral blood mononuclear cells were not affected. Chromanones 3p and 3r and 2-styrylchromones 3k potently activate the Nrf2 response in the AREc32 cell line at low micromolar concentrations (C5 3 μM). Compounds 3k and 3r are also the most active in inhibiting cell proliferation by 50 % after 72 h incubation at concentrations of 4.5 and 7.7 μM, whereas normal peripheral blood mononuclear cells were not affected.

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.

Synthesis and anti-inflammatory in vitro, in silico, and in vivo studies of flavone analogues

Chrysin and 7-hydroxy flavone were prepared by Baker-Venkatraman rearrangement followed by esterification at 7th position and replacement of ester with acetamide linking to different heterocyclic moieties synthesized 13a-g and 14a-g series of flavones analogues. These were screened against COX-2 and COX-1 enzymes for inhibition by in vitro assay and COX-2 for in silico docking studies. The compound 14a was found to be most active with IC50 of 3.11 μM concentration, with highest binding energy of -12.4 kcal/mole and 77.2 and 80.5 % inhibition at 3 and 5 h post-carrageenan induced in paw oedema.

Synthesis and cytotoxicity of novel chrysin derivatives

A series of chrysin derivatives 8a-8v were prepared and tested in vitro against HCT-116 (human colon cancer cell line), Hela (human cervical carcinoma cell line), DU-145 (human prostate cell line), K562 (human leukemia cell line), and SGC-7901 (human gastric cancer cell line). The chemical structures of these compounds were confirmed by means of MS, IR, 1H NMR, 13C NMR, and elemental analysis. Among these derivatives, 7-(2-(piperazin-1- yl)ethoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one, 8n, had the strongest activity against HCT-116, Hela, DU-145, K562, and SGC-7901 cells. Springer Science+Business Media, LLC 2010.

New synthesis of 1,3-diarylpropane-1,3-diones

1,3-Diarylpropane-1,3-diones have been synthesized by (i) UV irradiation and thermal rearrangement of o-aroyloxyacetophenones and (ii) microwave irradiation of aroyl chlorides and o-hydroyacetophenones.