Synthesis of derivatives of flavonoids

Siti Norliana Razali, Farediah Ahmad

Abstract


Chalcone is a subgroup of flavonoids that can be found abundantly in edible plants. Chalcones are becoming an interesting target class of compounds which are widely investigated due to their various biological activities. The aim of this study is to synthesize chalcones. Two derivatives of 4-hydroxybenzaldehyde were synthesized through methylation reaction using methyl iodide to obtain brown liquid of 4-methoxybenzaldehyde (36.60%) and prenylation reaction using 1-bromo-2-methyl-but-2-ene to yield 4-0-prenylbenzaldehyde (27.65%). The derivative of 3,4-dihdroxybenzaldehyde was synthesized by methylenation reaction with diiodomethane to furnish colourless oil of 3,4-methylenedioxybenzaldehyde (23.10%). 4-methoxybenzaldehyde was subjected to 2-hydroxyacetophenone in the presence of potassium hydroxide as a catalyst to afford 2’-hydroxy-4-methoxychalcone via aldol condensation reaction. All synthesized compounds were purified and characterized using spectroscopic methods, i.e. Fourier Transform-IR (FTIR) and proton Nuclear Magnetic Resonance (1H-NMR). The chromatographic purification followed by structural elucidation of the targeted chalcone will be carried out.

Keywords


Chalcone; methylation reaction; 4-hydroxybenzaldehyde; 4-methoxybenzaldehyde; prenylation reaction; 4-O-prenylbenzaldehyde; methylenation reaction; 3,4-methylenedioxybenzaldehyde; Claisen-Schmidt reaction

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References


Kazufumi, Y., Kanako, S. and Yusuke, T. (2009). Prenylation of aromatic compounds, a key diversification of plant secondary metabolites. Journal of Phytochemical. 8(23), 1-11.

Shashank, K. and Abhay, K. P. (2013). Chemistry and biological activities of flavonoids. The Scientific World Journal. 10,1-16.

Shashank, K. and Abhay, K. P. (2013). Phenolic content, reducing power and membrane protective activities of Solanum Xanthocarpum Root extracts. Vegetos. 26,301-307

Begum, E. A. and Rahmiye, E. (2011). Chemicals and structural properties of chalcones I. Journal of Pharmaceutical Science. 36, 223-242.

Erich, G. (2006). The science of flavonoids. Springer Science and Business Media, United State of America. 10, 1-46.

Chetana, B. P., Mahajan, S.K., and Suvarna, A. K. (2009). Chalcone: a versatile molecule. Journal of Pharmaceutical Sciences and Research. 1(3), 11-22.

Won, S. J., Liu, C. T., Ko, H. H., Wang, J. P., and Lin, C. N. (2005). Synthetic chalcones as potential anti-inflammatory and cancer chemo protective agents. European Journal of Medicinal Chemistry. 40,103-112

Yu, D. C., Panfilova, L. V., and Boreko, E. I. (1982). Synthesis and antiviral activity of unsaturated ketones of thiopene series. Pharmaceutical Chemicals. 16,103-105

Dong, X., Chen, J., Jiang, C., Liu, T., and Hu, Y. (2009). “Design, synthesis and biological evaluation of prenylated chalcones as vasorelaxant agents.” Arch. Pharm. (Weinheim). 342(7), 428-432.

Severi, F., Benvenuti, S., Costantino, L., Vampa, G., Melegari, M., and Antolini, L. (1998). Synthesis and activity of a new series of chalcones as aldose reductase inhibitors. European Journal of Medicinal Chemistry. 33 (11), 859-866.


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