4424-13-9

Usage

Class

Benzopyrans

Ring System

Contains a dioxolane ring system

Functional Group

Phenyl group attached to position 6

Influence of Phenyl Group

Influences chemical and physical properties significantly

Expected Behavior

Likely exhibits aromatic and heterocyclic behavior

Potential Uses

Synthesis of other organic compounds
Building block in the pharmaceutical industry

Unique Structure

Facilitates potential reactivity and warrants further investigation for properties and applications.

Upstream product

• 96249-79-5 2'-hydroxy-4',5'-methylenedioxychalcone 
• 533-31-3 Sesamol 
• 66003-50-7 1-<4,5-(methylenedioxy)-2-hydroxyphenyl>ethanone 
• 326-58-9 acetic acid benzo[1,3]dioxol-5-yl ester 
• 857982-72-0 3-hydroxy-1-(6-hydroxy-benzo[1,3]dioxol-5-yl)-3-phenyl-propan-1-one 
• 916486-99-2 6,7-dihydro-8H-1,3-dioxolo[4,5-g]benzopyran-8-one 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 
• 4720-68-7 4,5-methylenedioxy-2-hydroxybenzaldehyde 
• 20718-17-6 2-(dimethyl(oxo)-λ⁶-sulfaneylidene)-1-phenylethan-1-one 

Relevant academic research and scientific papers

Rhodium(III)-catalyzed one-pot synthesis of flavonoids from salicylaldehydes and sulfoxonium ylides

Rh(III)-catalyzed C–H activation of salicylaldehyde followed by an insertion reaction with sulfoxonium ylides and cyclization is applied to the synthesis of flavonoids. This one-pot strategy exhibits good functional group tolerance and gives flavones in moderate-to-good yields.

Identification and structure activity relationship of novel flavone derivatives that inhibit the production of nitric oxide and PGE2 in LPS-induced RAW 264.7 cells

In an effort to identify novel anti-inflammatory compounds, a series of flavone derivatives were synthesized and biologically evaluated for their inhibitory effects on the production of nitric oxide (NO) and prostaglandin E2 (PGE2), representative pro-inflammatory mediators, in LPS-induced RAW 264.7 cells. Their structure-activity relationship was also investigated. In particular, we found that compound 3g displayed more potent inhibitory activities on PGE2 production, similar inhibitory activities on NO production and less weak cytotoxicity than luteolin, a natural flavone known as a potent anti-inflammatory agent.

A versatile approach to flavones via a one-pot Pd(II)-catalyzed dehydrogenation/oxidative boron-Heck coupling sequence of chromanones

A variety of flavones were expediently synthesized from readily accessible chromanones via a one-pot sequence involving Pd(ii)-catalyzed dehydrogenation and oxidative boron-Heck coupling with arylboronic acid pinacol esters. In particular, the use of arylboronic acid pinacol esters was found to significantly improve the yield of the reaction.

Structure-activity relationship studies of flavonoids as potent inhibitors of human platelet 12-hLO, reticulocyte 15-hLO-1, and prostate epithelial 15-hLO-2

Human lipoxygenase (hLO) isozymes have been implicated in a number of disease states and have attracted much attention with respect to their inhibition. One class of inhibitors, the flavonoids, have been shown to be potent lipoxygenase inhibitors but their study has been restricted to those compounds found in nature, which have limited structural variability. We have therefore carried out a comprehensive study to determine the structural requirements for flavonoid potency and selectivity against platelet 12-hLO, reticulocyte 15-hLO-1, and prostate epithelial 15-hLO-2. We conclude from this study that catechols are essential for high potency, that isoflavones and isoflavanones tend to select against 12-hLO, that isoflavans tend to select against 15-hLO-1, but few flavonoids target 15-hLO-2.