33539-20-7

Usage

Preparation

Preparation from 2-hydroxy-6-methoxyacetophenone by persulfate oxidation (Elbs reaction) (26–33%).

Upstream product

• 703-23-1 2'-hydroxy-6'-methoxyacetophenone 
• 67-56-1 methanol 
• 1125-55-9 2-Acetyl-1,4-benzoquinone 
• 490-78-8 2,5-Dihydroxyacetophenone 
• 2555-29-5 8-acetyl-7-hydroxy-4-methyl-2H-chromen-2-one 
• 699-83-2 2,6-dihydroxylacetophenone 

Downstream Products

• 22248-13-1 1-(6-hydroxy-2,3-dimethoxyphenyl)ethan-1-one 
• 1187652-41-0 1-(3-benzyloxy-6-hydroxy-2-methoxy-phenyl)ethanone 
• 1349177-48-5 3-[6-(3-chloro-benzyloxy)-5-methoxy-4-oxo-4H-chromen-2-yloxymethyl]-benzonitrile 
• 1349177-50-9 2-benzyloxy-6-(3-chloro-benzyloxy)-5-hydroxy-chromen-4-one 
• 1349177-52-1 2,6-bis-(3-chloro-benzyloxy)-5-hydroxychromen-4-one 
• 1349177-54-3 6-(3-chloro-benzyloxy)-2-(4-chlorobenzyloxy)-5-hydroxy-chromen-4-one 
• 1349177-56-5 6-(3-chloro-benzyloxy)-2-(3,5-dichlorobenzyloxy)-5-hydroxy-chromen-4-one 
• 1349177-58-7 6-(3-chloro-benzyloxy)-5-hydroxy-2-(3-iodobenzyloxy)-chromen-4-one 
• 1349177-60-1 6-(3-chloro-benzyloxy)-5-hydroxy-2-(4-iodobenzyloxy)-chromen-4-one 
• 1349177-62-3 3-[6-(3-chloro-benzyloxy)-5-hydroxy-4-oxo-4H-chromen-2-yloxymethyl]-benzonitrile 
• 1349177-25-8 6-(3-chloro-benzyloxy)-5-methoxy-2-methylsulfanyl-chromen-4-one 
• 1349177-27-0 6-(3-chloro-benzyloxy)-2-methanesulfonyl-5-methoxy-chromen-4-one 
• 1349177-36-1 2-benzyloxy-6-(3-chloro-benzyloxy)-5-methoxychromen-4-one 
• 1349177-38-3 2,6-bis-(3-chloro-benzyloxy)-5-methoxychromen-4-one 

Relevant academic research and scientific papers

2-Arylmethylaminomethyl-5,6-dihydroxychromone derivatives with selective anti-HCV activity

Anti-HCV activity of aryl diketoacid (ADK) has been characterized by its two pharmacophoric elements, α,β-diketo acid moiety and substituted aryl ring. In this study, as a part of our ongoing efforts to discover a novel anti-HCV compound mimicking the ADK

CHEMOTHERAPEUTIC FLAVONOIDS, AND SYNTHESES THEREOF

Substituted flavonoid compounds, and pharmaceutical formulations of flavonoid compounds are described. Also described are processes for preparing flavonid compounds, as are methods for treating cancer in mammals using the described flavonoid compounds or pharmaceutical formulations thereof.

Synthesis and cancer chemopreventive activity of zapotin, a natural product from Casimiroa edulis

An efficient method has been developed to synthesize zapotin (5,6,2′,6′-tetramethoxyflavone), a component of the edible fruit Casimiroa edulis, on a multigram scale. The synthesis utilizes a regioselective C-acylation of a dilithium dianion derived from a substituted o-hydroxyactophenone to afford a β-diketone intermediate that can be cyclized to zapotin in good overall yield, thus avoiding the inefficient Baker-Venkataraman rearrangement pathway. Zapotin was found to induce both cell differentiation and apoptosis with cultured human promyelocytic leukemia cells (HL-60 cells). In addition, the compound inhibits 12-O-tetrade-canoylphorbol 13-acetate (TPA)-induced ornithine decarboxylase (ODC) activity with human bladder carcinoma cells (T24 cells), and TPA-induced nuclear factor-kappa B (NF-κB) activity with human hepatocellular liver carcinoma cells (HepG2 cells). These data suggest that zapotin merits further investigation as a potential cancer chemopreventive agent.

A New and Facile Iodine(III)-Mediated Approach for the Regioselective Alkoxylation of 2,5-Dihydroxyacetophenone

Oxidation of 2,5-dihydroxyacetophenone with iodobenzene diacetate (IBD) in different alcohols leads to regioselective alkoxylation, thereby providing a new and convenient route for the synthesis of 6-alkoxy-2,5- dihydroxyacetophenones.

Copper-catalysed oxidative alkoxylation of acyl- and carbomethoxy-hydroquinones

Oxidation of title hydroquinones by an [O2/CuICl] system in the presence of alcohols yields (71-88%) corresponding regioselectively 3-alkoxylated compounds. Compared with the classical procedure (silver oxide oxidation) in which alcohols have to be added to intermediate quinones in a second step, leading to a 1:1 mixture of starting material and final quinones, this new selective one-pot system does not oxidize alcohols and regenerates intermediate quinones from starting hydroquinones. Moreover, in situ trapping of the unstable formyl-quinone now allows the preparation of its 3-alkoxy derivative.

Gastroprotective flavone/flavanone compounds with therapeutic effect on inflammatory bowel disease

PCT No. PCT/KR97/00144 Sec. 371 Date Jan. 14, 1999 Sec. 102(e) Date Jan. 14, 1999 PCT Filed Jul. 25, 1997 PCT Pub. No. WO98/04541 PCT Pub. Date Feb. 5, 1998The present invention relates to novel flavone/flavanone compounds or their pharmaceutically acceptable salts and process for preparation thereof for protecting gastrointestinal tracts against gastritis, ulcers and inflammatory bowel disease.

5-HYDROXY-6,2'-DIMETHOXYFLAVONE FROM PRIMULA DENTICULATA

A novel natural flavone, 5-hydroxy-6,2'-dimethoxyflavone, was isolated from the leaf exudate of Primula denticulata.Its structure was elucidated by spectral studies and confirmed by synthesis.This flavone shows unusual fragments in its mass spectrum which