Synthesis and Biological Evaluation of Novel Saccharin Derivatives Containing 1,2,3-Triazole Moiety

doi:10.1007/s40242-015-4309-x

高等学校化学研究 ›› 2015, Vol. 31 ›› Issue (1): 71-77.doi: 10.1007/s40242-015-4309-x

Synthesis and Biological Evaluation of Novel Saccharin Derivatives Containing 1,2,3-Triazole Moiety

TANG Xiaobin^1,5, LI Zhenghui^1,5, LI Yonghong³, LIU Wei², YU Peng¹, LI Lixin⁵, GUO Yu⁴, YANG Cheng^4,5

1. College of Biotechnology, Tianjin 300457, P. R. China;
2. College of Sciences, Tianjin University of Science and Technology, Tianjin 300457, P. R. China;
3. State Key Laboratory of Element Organic Chemistry, Institute of Element Organic Chemistry, Tianjin 300071, P. R. China;
4. College of Pharmacy, Nankai University, Tianjin 300071, P. R. China;
5. High Throughput Molecular Drug Discovery Center, Tianjin International Joint Academy of Biotechnology and Medicine, Tianjin 300457, P. R. China

收稿日期:2014-08-15 修回日期:2014-10-13 出版日期:2015-02-01 发布日期:2014-11-03
通讯作者: LIU Wei, E-mail:liuwei2006@tust.edu.cn E-mail:liuwei2006@tust.edu.cn
基金资助:
Supported by the National Natural Science Foundation of China(No.21302139).

Synthesis and Biological Evaluation of Novel Saccharin Derivatives Containing 1,2,3-Triazole Moiety

TANG Xiaobin^1,5, LI Zhenghui^1,5, LI Yonghong³, LIU Wei², YU Peng¹, LI Lixin⁵, GUO Yu⁴, YANG Cheng^4,5

1. College of Biotechnology, Tianjin 300457, P. R. China;
2. College of Sciences, Tianjin University of Science and Technology, Tianjin 300457, P. R. China;
3. State Key Laboratory of Element Organic Chemistry, Institute of Element Organic Chemistry, Tianjin 300071, P. R. China;
4. College of Pharmacy, Nankai University, Tianjin 300071, P. R. China;
5. High Throughput Molecular Drug Discovery Center, Tianjin International Joint Academy of Biotechnology and Medicine, Tianjin 300457, P. R. China

Received:2014-08-15 Revised:2014-10-13 Online:2015-02-01 Published:2014-11-03
Contact: LIU Wei, E-mail:liuwei2006@tust.edu.cn E-mail:liuwei2006@tust.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(No.21302139).

摘要/Abstract

摘要：

A series of novel saccharin derivatives containing 1,2,3-triazole moiety was synthesized in satisfactory yields. The structures of all the compounds were elucidated and confirmed by Fourier transform infrared(FTIR) spectroscopy, ¹H and ¹³C nuclear magnetic resonance(¹H NMR, ¹³C NMR) spectroscopy, and high resolution mass spectrometry(HRMS). The bioassays indicated that most of the title compounds displayed some extent herbicidal activities at 100 μg/mL.

关键词: Saccharin, 1,2,3-Triazole, Biological activity, Herbicidal

Abstract:

Key words: Saccharin, 1,2,3-Triazole, Biological activity, Herbicidal

TANG Xiaobin, LI Zhenghui, LI Yonghong, LIU Wei, YU Peng, LI Lixin, GUO Yu, YANG Cheng. Synthesis and Biological Evaluation of Novel Saccharin Derivatives Containing 1,2,3-Triazole Moiety[J]. 高等学校化学研究, 2015, 31(1): 71-77.

参考文献

[1] Han L. Q., Wang L., Hou X. B., Fu H. S., Song W. G., Tang W. Q., Fan H., Bioorg. Med. Chem., 2014, 22, 1529
[2] D'Ascenzio M., Carradori S., Monte C. D., Secci D., Ceruso M., Supuran C. T., Bioorg. Med. Chem., 2014, 22, 1821
[3] Elsayed M. S. A., El-araby M. E., Serya R. A. T., El-Khatib A. H., Linscheid M. W., Abouzid K. A. M., Eur. J. Med. Chem., 2013, 61, 122
[4] Combrink K. D., Gulgeze H. B., Meanwell N. A., Pearce B. C., Zulan P., Bisacchi G. S., Roberts D. G. M., Stanley P., Seiler S. M., J. Med. Chem., 1998, 41, 4854
[5] Gençer N., Demir D., Sonmez F., Kucukislamoglu M., Bioorg. Med. Chem., 2012, 20, 2811
[6] Patane M. A., Dipardo R. M., Price R. P., Chang R. S. L., Ransom R. W., O'Malley S. S., Di Salvo J., Bock M. G., Bioorg. Med. Chem. Lett., 1998, 8, 2495
[7] Sunkel C. E., Fau de Casa-Juana M., Cillero F. J., Priego J. G., Ortega M. P., J. Med. Chem., 1988, 31, 1886
[8] Sommermeyer H., Schreiber R., Greuel J. M., De Vry J., Glaser T., Eur. J. Pharmacol., 1993, 240, 29
[9] Blanchet J., Macklin T., Ang P., Metallinos C., Snieckus V., J. Org. Chem., 2007, 72, 3199
[10] Youdim M. B., Ashkenazi R., Eur. J. Pharmacol., 1985, 119, 39
[11] TsUeda T., Konishi H., Manabe K., Angew. Chem. Int. Ed., 2013, 52, 8611
[12] Cochet T., Bellosta V., Greiner A., Roche D., Cossy J., Synlett., 2011, 13, 1920
[13] Xu J. M., Zhang E., Shi X. J., Wang Y. C., Yu B., Jia W. W., Guo Y. Z., Liu H. M., Eur. J. Med. Chem., 2014, 80, 593
[14] Kaushik C. P., Lal K., Kumar A., Kumar S., Med. Chem. Res., 2014, 23, 2995
[15] Ashok D., Gandhi D. M., Srinivas G., Kumar A. V., Med. Chem. Res., 2014, 23, 3005
[16] 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
[17] Kolb H. C., Sharpless K. B., Drug Discovery Today, 2003, 8(24), 1128
[18] Hlasta D. J., Ackerman J. H., J. Org. Chem., 1994, 59, 6184
[19] Jung P. J. M., Hueter O. F., Renold P., Pitterna T., Insecticidal Compounds, WO2012080376-A1, 2012
[20] Moeker J., Peat T. S., Bornaghi L. F., Vullo D., Supuran C. T., Poulsen S. A., J. Med. Chem., 2014, 57, 3522
[21] Zhao H. P., Liu Y. X., Cui Z. P., Beattie D., Gu Y. C., Wang Q. M., J. Agric. Food Chem., 2011, 59, 11711
[22] Zhao Q. Q., Liu S. H., Li Y. H., Wang Q. M., J. Agric. Food Chem., 2009, 57, 2849
[23] Kim S. H., Ramu R., Kwon S. W., Lee S. H., Kim C. H., Kang S. K., Rhee S. D., Bae M. A., Ahn S. H., Ha D. C., Cheon H. G., Kim K. Y., Ahn J. H., Bioorg. Med. Chem. Lett., 2010, 20, 1065
[24] Kwok S. W., Fotsing J. R., Fraser R. J., Rodionov V. O., Fokin V. V., Org. Lett., 2010, 12(19), 4217
[25] Kempe K., Krieg A., Becer C. R, Schubert U. S., Chem. Soc. Rev., 2012, 41, 176

Synthesis and Biological Evaluation of Novel Saccharin Derivatives Containing 1,2,3-Triazole Moiety

Synthesis and Biological Evaluation of Novel Saccharin Derivatives Containing 1,2,3-Triazole Moiety

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