Concise Synthesis of 5-Methoxy-6-hydroxy-2-methylchromone-7-O- and 5-Hydroxy-2-methylchromone-7-O-rutinosides. Investigation of Their Cytotoxic Activities against Several Human Tumor Cell Lines

Abstract

The synthesis of two novel 2-methylchromone-7-O-rutinosides, whose synthetic precursors and themselves in vitro biological activities have been investigated based on the cytotoxcity against several human tumor cell lines, was reported. The synthesis features early-stage assembly of the acidic labile glycosidic bond between sugar and 2-methylchromone aglycon under a phase transfer catalyzed glycosidation condition, whereas all the other standard glycosylation conditions specific to a wide array of rutinosyl donors bearing different anomeric leaving groups (e.g., SPh, OC(NH)CCl3, Br, OH groups) failed to furnish any detectable products.

Applications of Friedel–Crafts reactions in total synthesis of natural products

“…Flavonoids, a group of polyphenolic compounds that are abundant in plants, 590 include dietary components of potential importance to health. 591 In addition, flavanoids are emerging as a potentially significant unique group of pharmaceutical lead substrates.…”

“… 591 In addition, flavanoids are emerging as a potentially significant unique group of pharmaceutical lead substrates. 590 Among the several classes of flavonoids, dihydrochalcones exhibit a series of biologically remarkable activities, including antioxidant, 592,593 antiinflammatory, 594 antileishmanial, 595 antidiabetic, 596 anticancer 597 and molluscidal 598 properties. 599 Peng et al described the isolation and identification of a significant dihydrochalcone, named taccabulin E 633, from extracts of the plant species Tacca chantrieri and Tacca integrifolia .…”

Development of Fully and Partially Protected Fucosyl Donors for Oligosaccharide Synthesis

“…It was concluded that the problems observed with the two-stage glycosylation must occur after the bromination step. A number of literature examples of α-Fuc-(1–6)-GlcNAc synthesis highlight the extremely labile nature of the biologically important α-(1–6) linkage. , Kunz et al showed that the presence of arming groups such as benzyl protection on the fucose increase the instability of the α-(1–6) glycosidic bond . The highly reactive nature of the donor 7 , coupled with the sensitive glycosidic bond in the product 9 , was identified as the main reason for the low yields in the glycosylation reactions screened.…”

Combinatorial Synthesis of Structurally Diverse Triazole-Bridged Flavonoid Dimers and Trimers

“…Flavonoids are a large family of polyphenolic compounds that represent dietary constituents of importance to good health as well as a potentially important new class of pharmaceutical lead substrates [1,2,3]. There are several subclasses of flavonoids, including aurones, chalcones, coumarins, flavones and isoflavones, which serve as the core structural units of numerous biologically active molecules [4,5,6,7].…”