Design, Synthesis and Biological Evaluation of the Novel Antitumor Agent Aurone Derivatives

Abstract:

Aurones belong to a class of heterocyclic flavonoids which contains a benzofuran element associated with a benzylidene linked in position 2. Aurones possess a wide range of pharmacological activities and biological activities, such as antitumor, antifungal, phytoalexin and so on. A novel series of 2-ayl-yl (5-methacrylate) aurone analogues were synthesized in six steps with the overall yield of 11%-13% and characterized by ¹H NMR. Among the key intermediates and target compounds, 2-(2-furan-ylmethylene)-5-methacrylate-benzofuran-3(2H)-one (7a) and 2-(2-thienyl-ylmethylene)-5-methacrylate-benzofuran-3(2H)-one (7b) have never been reported before. Primary biological activities evaluation showed that 7a exhibited good inhibitory activities against K562 with an IC₅₀ of 2.18 μM and against HepG2 with an IC₅₀ of 3.95μM.

• Periodical: Advanced Materials Research (Volumes 781-784)
• Pages: 1235-1239
• DOI: https://doi.org/10.4028/www.scientific.net/AMR.781-784.1235
• Online since: September 2013
• Authors: Qian Nan Guo, Lei Lv, Yao Zhou, Peng Yu, Yuou Teng
• Keywords: Antitumor, Aurone Derivatives, Synthesis

References

[1] Elumalaia P, Liua HL. International Journal of Biological Macromolecules. Vol. 49(2011) p: 134.

[2] Brouillard R, Dangles O. The Flavonoids: Advances in Research since 1986. (Chapman and Hall. London, 1993).

[3] Information on http: /en. wikipedia. org/wiki/Aurone.

[4] Auf'mkolk M, Koehrle J and Hesch RD. et al. Biol. Chem. Vol. 261(1987) P. 11623.

[5] Boumendjel A. Curr Med Chem. Vol. 10(2003) P. 2621.

[6] Lawrence NJ, Rennison D, McGown AT et al. Bioorg Med Chem Lett. Vol. 13(2003) P. 3759.

[7] Huang W, Liu MZ and Li Y. Bioorganic & Medicinal Chemistry. Vol. 15(2007) P. 5191.

[8] Perrier E, Okombi S and Rival D, et al. Patent: EP1709964A2 (2006).

[9] Lee CY, Chew EH and Go ML. Eur J Med Chem. Vol. 45(2010) P. 2957.

[10] Ohkata K, Tamura and Shetuni BB et al. J Am Chem Soc Vol. 126(2004) P. 16783.

[11] Cheng C, Zhu SF and Liu B et al. J Am Chem Soc. Vol. 129(2007) P. 12616.

[12] Cheng H, Zhang L and Liu Y et al. Eur J Med Chem. Vol. 45(2010) P. 5950.

[13] Kim YJ, Kim JH and Park SB. Department of Chemistry. Vol. 11(2009) P. 17.

[14] Pires JR, Saito C and Suely L. Gomes, et al. J. Med. Chem. Vol. 44(2001) P. 3673.

[15] Lv L, Zhang XM and Lv J et al. Design, submitted to ICAB (2012).