Synthesis and PGE2 inhibitory activity of vinylated and allylated chrysin analogues

Abstract

Vinylated and allylated chrysin analogues were prepared as congeners of prenylated flavonoids and evaluated their anti-inflammatory activity. 8-Substituted chrysin analogues were prepared from 2'-hydroxy-3'-iodo-4',6'-dimethoxyacetophenone in 3 steps. 3-Allylated chrysin analogues were prepared from chrysin in 3 steps. Synthesized chrysin analogues (4, 5 and 8) showed moderate inhibitory activities of PGE2 production from LPS-induced RAW 264.7 cells.

Flavones modulate respiratory epithelial innate immunity: Anti-inflammatory effects and activation of the T2R14 receptor

“…Plants produce thousands of polyphenolic flavonoids (46 -49), which are of great biomedical interest, because they have effects on both eukaryotic and prokaryotic cells (47)(48)(49)(50)(51)(52)(53)(54)(55)(56)(57)(58). Flavones are a sub-group of flavonoids that have been demonstrated to have antibacterial, antioxidant, and anti-inflammatory effects in various in vitro models (48,51,53,55,57,59,60).…”

Synthesis and Transformation of Halochromones

“…The Stille reaction of 3-(trimethylstannyl)chromones 126 with 4-iodonitrobenzene afforded ring A substituted 4'-nitroisoflavones 127 (Scheme 42) [165]. Stille reaction of 3-bromo-5,7-di-O-methylchrysin with allyltributyltin in the presence of a catalytic amount of Pd(PPh 3 ) 4 in anhydrous DMF prompted the synthesis of 3-allyl-5,7-di-Omethylchrysin [171].…”

“…Vinyl and allyl groups were introduced to 8-iodo-5,7-di-Omethylchrysin 157 through Stille coupling, by reacting with vinylbutyltin or allylbutyltin in the presence of a catalytic amount of Pd(PPh 3 ) 4 in DMF as solvent (Scheme 52) [171].…”

Ionic Liquids and Ohmic Heating in Combination for Pd-Catalyzed Cross-Coupling Reactions: Sustainable Synthesis of Flavonoids

“…Due to their biological profile, numerous approaches have been reported for the synthesis of flavonoid derivatives. Among them, palladium-catalyzed cross-coupling reactions are gaining much recent interest [21][22][23][24][25][26][27], being the Suzuki-Miyaura coupling reaction the Given that ΩH is ideally suitable for synthesis in aqueous media, in which the reaction mixture is electrically conductive, water in combination with SILPC is a propitious solvent for this process. On the other hand, the combination of ΩH and water as solvent provides great opportunities for sustainable chemistry.…”

“…Due to their biological profile, numerous approaches have been reported for the synthesis of flavonoid derivatives. Among them, palladium-catalyzed cross-coupling reactions are gaining much recent interest [21][22][23][24][25][26][27], the Suzuki-Miyaura coupling reaction being the most frequently used methodology [28]. In this regard, ΩH-enhanced cross-coupling reactions, and especially Suzuki-Miyaura reactions, have proven particularly useful for the synthesis of pharmacologically relevant scaffolds [29,30].…”