Design, Synthesis and Biological Activities of Novel 4,5-Disubstituted-3-S-(β-D-acetylglycosyl)-1,2,4-triazole Derivatives

doi:10.1007/s40242-017-7053-6

Chemical Research in Chinese Universities ›› 2017, Vol. 33 ›› Issue (5): 758-764.doi: 10.1007/s40242-017-7053-6

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Design, Synthesis and Biological Activities of Novel 4,5-Disubstituted-3-S-(β-D-acetylglycosyl)-1,2,4-triazole Derivatives

CHENG Dandan¹, WEI Wei¹, LI Yuxin¹, HUA Xuewen², ZHOU Yunyun³, LIU Jingbo¹, LI Yonghong¹, YU Shujing¹, XIONG Lixia¹, LI Zhengming¹

1. State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering(Tianjin), College of Chemistry, Nankai University, Tianjin 300071, P. R. China;
2. College of Agriculture, Liaocheng University, Liaocheng 252000, P. R. China;
3. State Key Laboratory of Molecular Engineering of Polymers, Department of Macromolecular Science, Fudan University, Shanghai 200433, P. R. China

Received:2017-02-05 Revised:2017-03-21 Online:2017-10-01 Published:2017-07-21
Contact: LI Yuxin,E-mail:liyx128@nankai.edu.cn E-mail:liyx128@nankai.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(Nos.31370039, 21502229);the Tianjin Natural Science Foundation, China(No.16JCYBJC29400).

Abstract

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 andBotrytis 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.

Key words: 1,2,4-Triazole, S-β-D-acetylglycosyl, Biological activity

CHENG Dandan, WEI Wei, LI Yuxin, HUA Xuewen, ZHOU Yunyun, LIU Jingbo, LI Yonghong, YU Shujing, XIONG Lixia, LI Zhengming. Design, Synthesis and Biological Activities of Novel 4,5-Disubstituted-3-S-(β-D-acetylglycosyl)-1,2,4-triazole Derivatives[J]. Chemical Research in Chinese Universities, 2017, 33(5): 758-764.

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] Kaplanc?kl? Z. A., Özdemir A., Turan-Zitouni G., Alt?ntop M. D., 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., SuchetaKumari N., Eur. J. Med. Chem., 2009, 44(2), 551
[9] Giraud F., Loge C., Pagniez F., Crepin D., Le Page P., Le 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. Carbohyd. 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., Abdel 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

Design, Synthesis and Biological Activities of Novel 4,5-Disubstituted-3-S-(β-D-acetylglycosyl)-1,2,4-triazole Derivatives

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