Design, synthesis and biological activities of novel 4,5-disubstituted-3-S-(β-D-acetylglycosyl)-1,2,4-triazole derivatives

Abstract

A series of novel 4,5-disubstituted-3-S-(β-D-acetylglycosyl)-1,2,4-triazole derivatives was designed and synthesized via the strategy of introducing S-β-D-acetylglycosyl fragments into 1,2,4-triazole ring. The structures of 17 target compounds were characterized by means of ¹H NMR, ¹³C NMR and high-resolution mass spectrometer (HRMS). The results of insecticidal activity indicated that compound 5a displayed 60% lethality rate at 100 mg/L concentration. More importantly, the introduction of the carbohydrate fragment to the 1,2,4-triazole core could improve the insecticidal activities since the insecticidal activities of compounds 5 were better than those of compounds 4 and this result was also supported by calcium imaging technique. The antifungal activity of the target compounds showed that some novel compounds displayed moderate to good inhibition rate against Sclerotinia sclerotiorum and Botrytis cinerea, in which compound 5p exhibited 78.8% inhibition rate against Sclerotinia sclerotiorum and 68.6% inhibition rate against Botrytis cinerea. The herbicidal activities of compounds 5 against Brassica campestris indicated that most of the target compounds showed moderate to good activities, especially compound 5g which showed 52.9% herbicidal activity at the concentration of 200 mg/L.

Keywords

1,2,4-Triazole / S-β-D-acetylglycosyl / Biological activity

References

[1] Mi J. L., Zhou C. H., Bai X. Chinese J. Antibiot., 2007, 32(10): 587.

[2] Zhang Y., Qiao R. Z., Zhang Z. Y., Xu P. F., Zhang Z. Y., Wang Q., Mao L. M., Yu K. B. J. Chin. Chem. Soc., 2002, 49(3): 369.

[3] Winum J. Y., Rami M., Scozzafava A., Montero J. L. Med. Res. Rev., 2008, 28(3): 445.

[4] Kaplancıklı Z. A., Özdemir A., Turan-Zitouni G., Altıntop M. D. C., Can Ö. D. Eur. J. Med. Chem., 2010, 45(9): 4383.

[5] Stillings M. R., Welbourn A. P., Walter D. S. J. Med. Chem., 1986, 29(11): 2280.

[6] Botros S., Khalil N. A., Naguib B. H., El-Dash Y. Eur. J. Med. Chem., 2013, 60: 57.

[7] Yin K., Jiang L. H., Zhou H. X., Huang Y., Xiang J. N. Chinese J. Org. Chem., 2008, 28(6): 1016.

[8] Prasad D. J., Ashok M., Karegoudar P., Boja P., Holla B. S., Suche-taKumari N. Eur. J. Med. Chem., 2009, 44(2): 551.

[9] Giraud F., Loge C., Pagniez F., Crepin D. L., Page P. L., Borgne M. Bioorg. Med. Chem. Lett., 2008, 18(6): 1820.

[10] Xue S. J., Lu C. L. Chinese J. Org. Chem., 2008, 28(6): 1083.

[11] Wang B. L., Shi Y. X., Ma Y., Liu X. H., Li Y. H., Song H. B., Li B. J. J. Agric. Food Chem., 2010, 58(9): 5515.

[12] Dove A. Nat. Biotechnol., 2001, 19(10): 913.

[13] El-Sayed W. A., Fathi N. M., Gad W. A., El-Ashry E. S. H. J. Car-bohyd. Chem., 2008, 27(6): 357.

[14] Chen X. M., Li Z. J., Ren Z. X., Huang Z. T. Carbohyd. Res., 1999, 315(3/4): 262.

[15] Jacob G. S. Curr. Opin. Struct. Biol., 1995, 5(5): 605.

[16] Tian T., Cao L. H., Qian Z. S. Chinese J. Org. Chem., 2007, 27(6): 744.

[17] Thanh N. D., Mai N. T. T. Carbohyd. Res., 2009, 344(17): 2399.

[18] Bai S. T., Xiong D. C., Niu Y. H., Wu Y. F., Ye X. S. Tetrahedron, 2015, 71(30): 4909.

[19] Zhang R. B., Lu J. R., Liu J. B., Mu J. B., Yang X. Y., Wang H. Y., Wang M. J., Zhang H., Zhang M. Chem. J. Chinese Universities, 2015, 36(8): 1521.

[20] Feng Z. N., Lu J. R., Xin C. W., Li J. F., Bao X. R., Zhang T. T. Chem. J. Chinese Universities, 2013, 34(5): 1143.

[21] Li Y. X., Di F. J., Wang D. Y., Chen W., Wan Y. Y., Li Z. M. Chem. Res. Chinese Universities, 2015, 31(6): 952.

[22] Mao M. Z., Li Y. X., Zhou Y. Y., Yang X. P., Zhang X. L., Zhang X., Li Z. M. Chem. Res. Chinese Universities, 2013, 29(5): 900.

[23] El-Sayed W. A. A., Megeid R. E., Abbas H. A. S. Arch. Pharm. Res., 2011, 34(7): 1085.

[24] Martos M. B. Korosy F., Nature, 1950, 165: 369.

[25] Abbott W. S. J. Econ. Entomol., 1925, 18: 265.

[26] Collins C., Miller T. J. Exp. Biol., 1977, 67(1): 1.

[27] Zhang J. F., Xu J. Y., Wang B. L., Li Y. X., Xiong L. X., Li Y. Q., Ma Y., Li Z. M. J. Agric. Food Chem., 2012, 60: 7565.

[28] Liu J. B., Li Y. X., Zhang X. L., Hua X. W., Wu C. C., Wei W., Wan Y. Y., Cheng D. D., Xiong L. X., Yang N., Song H. B., Li Z. M. J. Agric. Food Chem., 2016, 64: 3697.

[29] Liu Z. M., Yang G. F., Qin X. H. J. Chem. Technol. Biotechnol., 2001, 76(11): 1154.

[30] Wang B. L., Duggleby R. G., Li Z. M., Wang J. G., Li Y. H., Wang S. H., Song H. B. Pest Manag. Sci., 2005, 61(4): 407.

[31] Yan K., Liu M. G. J. China Three Gorges Univ.(Natural Sciences), 2011, 33(3): 103.