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Chinese Journal of Organic Chemistry >

2012 , Vol. 32 >Issue 02: 333 - 337

DOI: https://doi.org/10.6023/cjoc1108081

Articles

Synthesis of Novel Isoxazole Contained Rupestonic Acid Derivatives and in vitro Inhibitory Activity against Influenza Viruses A and B

  • ZHAO Jiang-Yu ,
  • Aisa Haji Akber
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  • a Key Laboratory of Chemistry of Plant Resources in Arid Region, Xinjiang Technical Institute of Physics and Chemistry,Chinese Academy of Sciences, Urumqi 830011;
    b Graduate School of Chinese Academy of Sciences, Beijing 100039

Received date: 2011-08-08

  Revised date: 2011-09-14

  Online published: 2012-03-09

Supported by

Project supported by the High-tech Research and Development Program of Xinjiang (No. 200910105), the National Natural Science Foundation of China (No. 20872174) and the China National Science Fund for Distinguished Young Scholars (No. 30925045).

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Abstract

To improve biological activity of rupestonic acid, six rupestonic acid amide derivatives containing isoxazole were synthesized in the presence of DCC, HOBt/DMAP using the rupestonic acid and 3-aryl-5-isoxazole-methylamine as the starting materials. The synthesized compounds 3a～3f were confirmed by the methods of 1H NMR, 13C NMR, IR, ESI-MS techniques and preliminarily assayed in vitro against influenza viruses A and B. The results showed that compound 3c showed better activity against both influenza viruses A (H3N2) and B, and compounds 3c and 3e had the higher inhibition against influenza B virus than the parent compound 1.

Key words： rupestonic acid; isoxazole derivative; influenza virus; inhibitory activity

Cite this article

ZHAO Jiang-Yu , Aisa Haji Akber . Synthesis of Novel Isoxazole Contained Rupestonic Acid Derivatives and in vitro Inhibitory Activity against Influenza Viruses A and B[J]. Chinese Journal of Organic Chemistry, 2012 , 32(02) : 333 -337 . DOI: 10.6023/cjoc1108081

References

[1] Tosh, P. K.; Poland, G. A. Expert Opin. Emerg. Drugs 2008, 13, 21.

[2] Moscona, A. New Engl. J. Med. 2005, 353, 1363.

[3] Russell, R. J.; Haire, L. F.; Stevens, D. J.; Collins, P. J.; Lin, Y. P.; Blackburn, G. M.; Hay, A. J.; Gamblin, S. J.; Skehel, J. J. Nature 2006, 443, 45.

[4] Mai, L. Q.; Maki, K.; Kazuhiko, S.; Sakai, Y. T.; Hien, N. T.; Nguyen, K. H. L.; Pham, N. D.; Negyn, H. H. Nature 2005, 437, 1108.

[5] Chen, X. Y.; Wang, S. H. Chin. Trad. Herb. Drugs 1981, 12, 25 (in Chinese). (陈希元, 王绍华, 中草药, 1981, 12, 25.)

[6] Zhang, B. H.; Wang, Y. N.; Zhang, Y. Q. Chin. J. Modren Med. 2005, 15, 1968 (in Chinese). (张炳华, 王亚男, 张彦琼, 中国现代医学杂志, 2005, 15, 1968.)

[7] Sirafil; Gulnar; Liu, F. J. Med. Chin. Minorities 1996, 2, 35 (in Chinese). (斯拉甫, 古力娜, 刘发, 中国民族医药杂志, 1996, 2, 35.)

[8] Sirafil; Abdiryim; Gulnar Chin. J. Integr. Trad. Western Med. 2002, 22, 126 (in Chinese). (斯拉甫, 阿不都热依木, 古力娜, 中国中西医结合杂志, 2002, 22, 126.)

[9] Aisa, H. A.; Yong, J. P.; Lv, Q. Y.; Wu, T. Acta Crystallogr. E 2008, 64, o479.

[10] Ma, Y. M.; Aisa, H. A.; Liao, L. X.; Aibai, S.; Zhang, T.; Ito, Y. J. Chromatogr. A 2005, 1076, 198.

[11] Yong, J. P.; Aisa, H. A. Chem. Nat. Compd. 2008, 44, 311.

[12] Yong, J. P.; Aisa, H. A. Chin. J. Org. Chem. 2008, 28, 1807 (in Chinese). (雍建平, 阿吉艾克拜尔·艾萨, 有机化学, 2008, 28, 1807.)

[13] Yong, J. P.; Lv, Q. Y.; Aisa, H. A. Bull. Korean Chem. Soc. 2009, 30, 435.

[14] Tang, L. D.; Wang, J. W.; Zhang, S. J.; Yong, J. P. Chin. Trad. Herb. Drugs 2006, 37, 332 (in Chinese). (汤立达, 王建武, 张士俊, 雍建平, 中草药, 2006, 37, 332.)

[15] Liu, L. J.; Yong, J. P.; Wang, J. W.; Wang, X. Z.; Jia, J. Chem. J. Chin. Univ. 2006, 27, 1669 (in Chinese). (刘利军, 雍建平, 王建武, 王西照, 贾炯, 高等学校化学学报, 2006, 27, 1669.)
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