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Synthesis of Brominated Quercetin Derivatives Using Distinct Brominating Systems
Corresponding Author(s) : Xiaoping Yang
Asian Journal of Chemistry,
Vol. 26 No. 15 (2014): Vol 26 Issue 15
Abstract
6,8-Dibromoquercetin derivatives were obtained through reaction of quercetin with HBr-H2O2. On the other hand, quercetin reacted with bromine to synthesize poly brominated derivatives. The reaction procedures were monitored by either TLC or HPLC or both in some cases. The reaction products were further purified via either recrystallization or silica gel column chromatography. Then the chemical structures were further confirmed by 1H NMR and LC-MS. Two new quercetin brominated derivatives, namely 6,8-dibromoquercetin and 6,8,2',5',6'-pentabrominated quercetin were obtained. Two distinct brominated approaches were studied to obtain two different quercetin brominated derivatives, 6,8-dibromoquercetin and 6,8,2',5',6'-pentabrominated quercetin with the yields of 80 and 70 %, respectively.
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- M.A. Baig, V.B. Gawali, R.R. Patil and S.R. Naik, J. Nat. Med., 66, 500 (2012); doi:10.1007/s11418-011-0614-y.
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- Yong-Sheng Dai, Master’s Degree Thesis, The Structural Design and Synthesis of Flavonoid Derivatives, Harbin Engineering University, (2006).
- J. Tan, W. Bo-Chu and Z. Lian-Cai, Chinese Pharm. J., 41, 1688 (2006).
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References
M.A. Baig, V.B. Gawali, R.R. Patil and S.R. Naik, J. Nat. Med., 66, 500 (2012); doi:10.1007/s11418-011-0614-y.
S.L. Pinto, J. Kumar, G. Partha and R.A. Bechtol, Clinicoecon Outcomes Res., 5, 153 (2013); doi:10.2147/CEOR.S40735.
L. Cialdella-Kam, D.C. Nieman, W. Sha, M.P. Meaney, A.M. Knab and R.A. Shanely, Br. J. Nutr., 109, 1923 (2012); doi:10.1017/S0007114512003972.
F. Boers, G. Lemiere, J.A. Lepoivre, A. De Groot, R. Dommisse, T. De Bruyne, A.J. Vlietinck and D.A. Vanden Berghe, Pharmazie, 53, 512 (1998).
C. Hu, Z. Jian-ping and H. Shao, The Synthesis Research of Quercetin Derivatives, Medicinal Chemistry, National Conference Proceedings (China), p. 159 (2005).
Yong-Sheng Dai, Master’s Degree Thesis, The Structural Design and Synthesis of Flavonoid Derivatives, Harbin Engineering University, (2006).
J. Tan, W. Bo-Chu and Z. Lian-Cai, Chinese Pharm. J., 41, 1688 (2006).
B. Zhao, Q.H. Xu and L.Y. Duan, Chemical Reagents, 28, 141 (2006).
M. Ichikawa, S. Hibino, M. Onishi, J.F. Hatcher, A.M. Pamukcu and G.T. Bryan, Org. Prep. Proced. Int., 17, 56 (1985); doi:10.1080/00304948509355470
V.V. Polyakov, Chem. Nat. Compd., 35, 21 (1999); doi:10.1007/BF02238204.