Synthesis and Antifungal, Anti-tumor Studies of the Trisubstitued Triazines Bearing Aminopyrimidine Group

Chin. J. Org. Chem. ›› 2011, Vol. 31 ›› Issue (08): 1266-1271. Previous Articles Next Articles

Notes

含嘧啶氨基的三取代三嗪衍生物的合成及其抗菌、抗肿瘤活性研究

陈华*^,1，谷云景¹，苑香果¹，赵莲¹，赵建鹏¹，秦占斌¹，刘丽²，李小六*^,1，曹克强²，张金超¹

(¹河北大学化学与环境科学学院河北省化学生物学重点实验室保定 071002)
(²河北农业大学植物保护学院保定 071001)

收稿日期:2011-01-11 修回日期:2011-03-12 发布日期:2011-03-12
通讯作者: 陈华 E-mail:hua-todd@163.com

Synthesis and Antifungal, Anti-tumor Studies of the Trisubstitued Triazines Bearing Aminopyrimidine Group

Chen Hua*^,1 Gu Yunjing¹ Yuan Xiang-guo¹ Zhao Lian¹ Zhao Jianpeng¹ Qin Zhanbin¹ Liu Li² Li Xiaoliu*^,1 Cao Keqiang² Zhang Jinchao¹

(¹Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002)
(²College of Plant Protec-tion, Hebei Agricultural University, Baoding 071001)

Received:2011-01-11 Revised:2011-03-12 Published:2011-03-12

A series of novel trisubstituted 1,3,5-triazine compounds bearing aminopyrimidine group were synthesized using cyanuric chloride as the starting material. The antifungal activitiy against Valsa mali and antiproliferative activity for three tumor cells of all the triazine compounds were evaluated. The results showed that a majority of the compounds 2aa～2cb and 3aa～3cb have notable inhibitory activity against Valsa mali. Some compounds, such as 4ba and 4ca, showed good cytotoxicity to BGC-823 and Hela tumor cells with the IC₅₀ value of 10.9 and 11.3 μmol/L, respectively, higher than that of the positive control cisplatin.

Key words: aminopyrimidine, triazine, antifungal activity, anti-tumor activity

Cite this article

CHEN Hua, GU Yun-Jing, YUAN Xiang-Guo, ZHAO Lian, ZHAO Jian-Peng, QIN Zhan-Bin, LIU Li, LI Xiao-Liu, CAO Ke-Qiang, ZHANG Jin-Chao. Synthesis and Antifungal, Anti-tumor Studies of the Trisubstitued Triazines Bearing Aminopyrimidine Group[J]. Chin. J. Org. Chem., 2011, 31(08): 1266-1271.

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参考文献

[1] Zhou, C. H.; Min, J.; Liu, Z. G.; Young, A.; Deshazer, H.; Gao, T. ; Chang, Y.-T. ; Kallenbach, N. R. Bioorg. Med. Chem. Lett. 2008, 18, 1308.

[2] Srinivas, K.; Srinivas, U.; Jayathirtha Rao, V.; Bhanuprakash, K.; Harakishore, K.; Murty, U. S. N. Bioorg. Med. Chem. Lett. 2005, 15, 1121.

[3] Srinivas, K.; Srinivas, U.; Bhanuprakash, K.; Harakishore, K.; Murty, U. S. N.; Jayathirtha Rao, V. Eur. J. Med. Chem. 2006, 41, 1240.

[4] Nie, Z.; Perretta, C.; Erickson, P.; Margosiak, S.; Almassy, R.; Lu, J.; Averill, A.; Yager, K. M.; S Chu, S.-S. Bioorg. Med. Chem. Lett. 2007, 17, 4191.

[5] Zheng, M. F.; Xu, C. H.; Ma, J. W.; Sun, Y.; Du, F. F.; Liu, H.; Lin, L. P.; Li, C.; Ding, J.; Chen, K. X.; Jiang, H. L. Bioorg. Med. Chem. 2007, 15, 1815.

[6] Kuo, G. H.; DeAngelis, A.; Emanuel, S.; Wang, A.; Zhang, Y.; Connolly, P. J.; Chen, X.; Gruninger, R. H.; Rugg, C.; Fuentes, P. A. J. Med. Chem. 2005, 48, 4535.

[7] Huang, W. W.; Zheng, W.; Urban, D. J.; Inglese, J.; Sidransky, E.; Austin, C. P.; Thomas, C. J. Bioorg. Med. Chem. Lett. 2007, 17, 5783.

[8] Agarwal, A.; Srivastava, K.; Puri, S. K.; Chauhan, P. M. S. Bioorg. Med. Chem. Lett. 2005, 15, 531.

[9] Baindur, N.; Chadha, N.; Brandt, B. M.; Asgari, D.; Patch, R. J.; Schalk-HiHi, C.; Carver, T. E.; Petrounia, I. P.; Baumann, C. A.; Ott, H.; Springer, B. A.; Player, M. R. J. Med. Chem. 2005, 48, 1717.

[10] Arya, K.; Dandia, A. Bioorg. Med. Chem.Lett. 2007, 17, 3298.

[11] Klenke, B.; Stewart, M.; Barrett, M. P.; Brun, R.; Gilbert, I. H. J. Med. Chem. 2001, 44, 3440.

[12] Son, Y.-A.; Park, Y.-M.; Park, S.-Y.; Shin, C.-J.; Kim, S.-H. Dyes and Pigments 2007, 73, 76.

[13] Menicagli, R.; Samaritani, S.; Signore, G.; Vaglini, F.; Via, L. D. J. Med. Chem. 2004, 47, 4649.

[14] Brzozowski, Z.; Saczewski, F.; Gdaniec, M. Eur. J. Med. Chem. 2000, 35, 1053.

[15] Rose, Y.; Ciblat, S.; Reddy, R.; Belley, A. C.; Dietrich, E.; Lehoux, D.; McKay, G. A.; Poirier, H.; Rafai Far, A.; Delorme, D. Bioorg. Med. Chem. Lett. 2006, 16, 891.

[16] Rawal, R. K.; Tripathi, R.; Katti, S. B.; Pannecouque, C.; De Clercq, E. Eur. J. Med. Chem. 2008, 43, 2800.

[17] Chen, H.; Bai, J.; Jiao, L.-L.; Guo, Z.-H.; Yin, Q.-M.; Li, X.-L. Bioorg. Med. Chem. 2009, 17, 3980.

[18] Liu, C.-L. Pesticides 1995, 34(8), 25 (in Chinese).

(刘长令农药 1995, 34(8), 25.)

[19] Chen, H.; Bai, J.; Zhao, L.; Yuan, X.-G.; Li, X.-L.; Cao, K.-Q. Chin. J. Org. Chem. 2009, 29(1), 94 (in Chinese).

(陈华，白洁，赵莲，苑香果，李小六，曹克强有机化学 2009, 29(1), 94.)

[20] Chen, H.; Yuan, X.-G.; Qin, Z.-B.; Zhao, J.-P.; Li, X.-L.; Zhang, J.-C. Chin. J. Org. Chem. 2010, 30(4), 611 (in Chinese).

(陈华，苑香果，秦占斌，赵建鹏，李小六，张金超有机化学 2010, 30(4), 611.)

[21] Xu, J.-X. Progress in Chemistry 2007, 19, 700 (in Chinese).

(许家喜化学进展，2007, 19, 700.)

[22] Kappe, C. O. Angew. Chem. Int. Ed. 2004, 43, 6250.

[23] Mosmann, T. J. Immunol. Meth. 1983, 65, 55.

含嘧啶氨基的三取代三嗪衍生物的合成及其抗菌、抗肿瘤活性研究

Synthesis and Antifungal, Anti-tumor Studies of the Trisubstitued Triazines Bearing Aminopyrimidine Group

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