Efficient Synthesis of Frutinone A and Its Derivatives through Palladium‐Catalyzed CH Activation/Carbonylation. Issue 4 (22nd September 2014)

• Record Type: Journal Article
• Authors: Shin, Yongje; Yoo, Changho; Moon, Youngtaek; Lee, Yunho; Hong, Sungwoo
• Is Part Of: Chemistry, an Asian journal. Volume 10:Issue 4(2015:Apr.)
• Page Start: 878
• Page End: 881
• Publication Date: 2014-09-22
• Subjects: carbonylation -- CH functionalization -- frutinone A -- palladium -- structure–activity relationships; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/asia.201402876
• Languages: English
• ISSNs: 1861-4728

Abstract

Abstract: Frutinone A, a biologically active ingredient of an antimicrobial herbal extract, demonstrates potent inhibitory activity towards the CYP1A2 enzyme. A three‐step total synthesis of frutinone A with an overall yield of 44 % is presented. The construction of the chromone‐annelated coumarin core was achieved through palladium‐catalyzed CH carbonylation of 2‐phenolchromones. The straightforward synthetic route allowed facile substitutions around the frutinone A core and thus rapid exploration of the structure–activity relationship (SAR) profile of the derivatives. The inhibitory activity of the synthesized frutinone A derivatives were determined for CYP1A2, and ten compounds exhibited one‐to‐two digit nanomolar inhibitory activity towards the CYP1A2 enzyme. Abstract : Bearing frutinone : A three‐step total synthesis of frutinone A (see scheme) with an overall yield of 44 % is presented. The construction of the chromone‐annelated coumarin core was achieved through palladium‐catalyzed CH carbonylation of 2‐phenolchromones. The straightforward synthetic route allowed facile substitutions around the frutinone A core and thus rapid exploration of the structure–activity relationship profile of the derivatives.