Chinese Journal of Organic Chemistry >
Synthesis and Preliminary Antitumor Activities of Aurone Derivatives
Received date: 2013-05-20
Revised date: 2013-07-10
Online published: 2013-08-12
Supported by
Project supported by the National Natural Science Fundation of China (Nos. 20872118, 30070905), the Key Laboratory Fund of Shaanxi Province of China (Nos. 2010JS097, 11JS090, 12JS110) and the Foundation of the Education Department of Shaanxi Province (No. 12JK1010).
Aurones are an important type of flavonoids with broad biological activities and pharmacological effects, such as anti-tumor, anti-inflammatory, antioxidant, antibacterial, insect antifeedant etc. They are less common and not widely distributed in nature. The low contents in nature lead to high cost of extraction and separation. In order to extend the compounds diversity and study structure activity relationship, phenoxyacetic acid, 2,3,5-trimethylphenol, 4-chlorol-3,5-dimethylphenol, chloroacetic acid and various aromatic aldehydes are used as starting materials to synthesize three types of aurone derivatives. Their structures were characterized by melting point, 1H NMR, 13C NMR, ESI-MS and elemental analysis. Nine of twenty five synthetic compounds 2h～2m, 5a～5c were unreported in the literature. All the target compounds were evaluated for antitumor activities against Hela human cervical carcinoma cell lines by methyl thiazolyl tetrazolium (MTT) method. The results showed that compounds 2b, 5b, 2s and 2g exhibited potentially high activity against Hela human cervical carcinoma cell lines with IC50 value of 44.3, 31.1, 43.8 and 41.9 μmol/L.
Huang Xinwei , Wang Zheng , Chen Qiaoli , Sun Yanni , Wang Cuiling , Liu Zhulan , Liu Jianli . Synthesis and Preliminary Antitumor Activities of Aurone Derivatives[J]. Chinese Journal of Organic Chemistry, 2013 , 33(12) : 2565 -2571 . DOI: 10.6023/cjoc201305032
[1] Huang, W.; Liu, M. Z.; Li, Y.; Tan, Y.; Yang, G. F. Bioorg. Med. Chem. 2007, 15, 5191.
[2] Lawrence, N. J.; Rennison, D.; McGown, A. T.; Hadfield, J. A. Bioorg. Med. Chem. Lett. 2003, 13, 3759.
[3] Lewin, G.; Aubert, G.; Thoret, S.; Dubois, J.; Cresteil, T. Bioorg. Med. Chem. 2012, 20, 1231.
[4] Bandgar, B. P.; Patil, S. A.; Korbad, B. L.; Biradar, S. C.; Nile, S. N.; Khobragade, C. N. Eur. J. Med. Chem. 2010, 45, 3223.
[5] Sheng, R.; Xu, Y.; Hu, C. Q.; Zhang, J.; Lin, X.; Li, J. Y.; Yang, B.; He, Q. J.; Hu, Y. Z. Eur. J. Med. Chem. 2009, 44, 7.
[6] Thanigaimalai, P.; Yang, H. M.; Sharma, V. K.; Kim, Y.; Jung, S. H. Bioorg. Med. Chem. 2010, 18, 4441.
[7] Shin, S. Y.; Shin, M. C.; Shin, J. S.; Lee, K. T.; Lee, Y. S. Bioorg. Med. Chem. Lett. 2011, 21, 4520.
[8] Manjulatha, K.; Srinivas, S.; Mulakayala, N.; Rambabu, D.; Prabhakar, M.; Arunasree, K. M.; Alvala, M.; Rao, M. V. B.; Pal, M. Bioorg. Med. Chem. Lett. 2012, 22, 6160.
[9] Sim, H. M.; Wu, C. P.; Ambudkar, S. V.; Go, M. L. Biochem. Pharmacol. 2011, 82, 1562.
[10] Sim, H. M.; Lee, C. Y.; Ee, P. L. R.; Go, M. L. Eur. J. Pharm. Sci. 2008, 35, 293.
[11] Starcevic, S.; Turk, S.; Brus, B.; Cesar, J.; Rizner, T. L.; Gobec, S. J. Steroid Biochem. 2011, 127, 255.
[12] Detsi, A.; Majdalani, M.; Kontogiorgis, C. A.; Litina, D. H.; Kefalas, P. Bioorg. Med. Chem. 2009, 17, 8073.
[13] Morimoto, M.; Fukumoto, H.; Nozoe, T.; Hagiwara, A.; Komai, K. J. Agric. Food Chem. 2007, 55, 700.
[14] Cheng, H. M.; Zhang, L. W.; Liu, Y. X.; Chen, S. P.; Cheng, H.; Lu, X.; Zheng, Z. X.; Zhou, G. C. Eur. J. Med. Chem. 2010, 45, 5950.
[15] Sim, H. M.; Loh, K. Y.; Yeo, W. K.; Lee, C. Y.; Go, M. L. ChemMedChem 2011, 6, 713.
[16] Haudecoeur, R.; Belkacem, A. A.; Yi, W.; Fortune, A.; Brillet, R.; Belle, C.; Nicolle, E.; Pallier, C.; Pawlotsky, J. M.; Boumendjel, A. J. Med. Chem. 2011, 54, 5395.
[17] Lee, C. Y.; Chew, E. H.; Go, M. L. Eur. J. Med. Chem. 2010, 45, 2957.
[18] Thakkar, K.; Cushman, M. J. Org. Chem. 1995, 60, 6499.
[19] Donnelly, J. A.; Emerson, G. M. Tetrahedron 1990, 46, 7227.
[20] Bose, G.; Mondal, E.; Khan, A. T.; Bordoloi, M. T. Tetrahedron Lett. 2001, 42, 8907.
[21] Harkat, H.; Blanc, A.; Weibel, J. M.; Pale, P. J. Org. Chem. 2008, 73, 1620.
[22] Yu, M.; Lin, M.; Han, C. Y.; Zhu, L.; Li, C. J.; Yao, X. Q. Tetrahedron Lett. 2010, 51, 6722.
[23] Kraus, G. A.; Gupta, V. Org. Lett. 2010, 12, 5278.
[24] Deshpande, A. R.; Paradkar, M. V. Synth. Commun. 1990, 20, 809.
[25] Venkateswarlu, S.; Panchagnula, G. K.; Gottumukkala, A. L.; Subbaraju, G. V. Tetrahedron 2007, 63, 6909.
[26] Imafuku, K.; Honda, M.; McOmie, J. F. W. Synthesis 1987, 199.
[27] Litkei, G.; Patonay, T. Acta Chim. Hung. 1983, 114, 47.
[28] Okombi, S.; Rival, D.; Bonnet, S.; Mariotte, A. M.; Perrier, E.; Boumendjel, A. J. Med. Chem. 2006, 49, 329.
[29] Sen, B. J. Am. Chem. Soc. 1952, 74, 3445.
[30] Clark, C. R.; Halfpenny, P. R.; Hill, R. G.; Horwell, D. C.; Hughes, J.; Jarvis, T. C.; Rees, D. C.; Schofield, D. J. Med. Chem. 1988, 31, 831.
[31] Brown, J. P.; McCall, E. B. J. Chem. Soc. 1957, 0, 3875.
[32] Smith, L. I.; Holmes, R. R. J. Am. Chem. Soc. 1951, 73, 4294.
[33] Mosmann, T. J. Immunol. Methods 1983, 65, 55.
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