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Relevant academic research and scientific papers

Synthesis of 6- or 8-bromo flavonoids by regioselective mono-bromination and deprotection protocol from flavonoid alkyl ethers

C-6 and C-8 monobromo flavonoids are important building blocks for the synthesis of flavonoid natural products and their derivatives. Bromination of suitably alkylated flavonoids with N-bromosuccinimide in dichloromethane (DCM), followed by deprotection with BCl3, gives either a C-6 or a C-8 monobromo flavonoid in high yield and with high regioselectivity, depending on the protection pattern of the C-5 and C-7 OH groups. The mild and neutral conditions are particularly useful for the regioselective bromination of acid-labile substrates.

Total synthesis of 8-(6″-umbelliferyl)-apigenin and its analogs as anti-diabetic reagents

The naturally occurring flavone 8-(6″-umbelliferyl)apigenin, a hybrid structure of apigenin and coumarin, as well as seven of its analogues were synthesized for the first time by using iodination and Suzuki coupling reactions as key steps. The synthesis of 8-(6″-umbelliferyl)-apigenin was achieved in seven linear steps from the commercially available 1-(2,4,6-trihydroxyphenyl)ethan-1-one and 7-hydroxyl coumarine with 31% overall yield. Effects of these compounds on glucose disposal were investigated in adipocytes. All of the flavonoid and coumarin hydrids were found to have better bioactivities than their corresponding flavonoid cores. The most potent compound 15 (10?μΜ) could promote glucose consumption by 57% which exhibited similar effect as the positive control metformin at 1?mM. Moreover, fluorescence microscopy showed that four 8-(6″-umbelliferyl)apigenin analogues 2, 15, 30 and 31 could promote the 2-NBDG uptake into 3T3-L1 cells, which consist with those observed in the regulation of glucose.