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Synthesis Of Regioselectively Acylated Quercetin Analogues With Improved Antiplatelet Activity, Yu Duan, Na Sun, Min Xue, Xiaolan Wang, Hu Yang
Synthesis Of Regioselectively Acylated Quercetin Analogues With Improved Antiplatelet Activity, Yu Duan, Na Sun, Min Xue, Xiaolan Wang, Hu Yang
Chemical and Biochemical Engineering Faculty Research & Creative Works
The aim of the present study was to report on a complete synthetic approach, namely benzylation-hydrolysis-acylation-hydrogenation, to the synthesis of regioselectively acylated quercetin analogues using low-cost rutin as a starting material. Three quercetin analogues, quercetin-3-O-propionate (Q-pr), quercetin-3-O-butyrate (Q-bu) and quercetin-3-O-valerate (Q-va), containing 3-, 4- and 5-carbon aliphatic acyl chains, respectively, were synthesized and characterized with 1H nuclear magnetic resonance (NMR), 13C NMR and mass spectrometry. Compared with quercetin, all three analogues exhibited improved lipophilicity. The lipophilicity of the analogue increased with increasing acyl chain length. Q-va exhibited the highest lipophilicity among the three analogues, but a lower water …