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Chinese Journal of Organic Chemistry >

2018 , Vol. 38 >Issue 5: 1147 - 1154

DOI: https://doi.org/10.6023/cjoc201712017

Articles

Synthesis and Preliminary Anti-bovine Viral Diarrhea Virus (BVDV) Activity Evaluation of Morpholine Nucleoside Analogues and Their Sulfonamide Derivatives

  • Hua Yingchun ,
  • He Bin ,
  • Qin Zhiyan ,
  • Wang Song ,
  • Liu Huiping ,
  • Liu Fengwu
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  • a School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou 450001;
    b Collaborative Innovation Center of Henan New Drug Research and Safety Evaluation, Zhengzhou 450001

Received date: 2017-12-08

  Revised date: 2018-01-10

  Online published: 2018-01-26

Supported by

Project supported by the National Natural Science Foundation of China (No. 21372207).

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Abstract

A series of morpholine nucleoside analogues were synthesized starting from ribonucleosides, and then the morpholine nucleoside sulfonamide derivatives were obtained by treated with N-acetylsulfanilyl chloride. The obtained compounds were confirmed by HRMS, 1H NMR and 13C NMR spectral analysis. The bovine kidney cells infected with bovine viral diarrhea virus (BVDV) were used as models to screen the antiviral activity of the target compounds. But the results did not show desired potent antiviral activity.

Key words： nucleoside analogue; morpholine nucleoside; sulfonamides derivative; anti-BVDV activity

Cite this article

Hua Yingchun , He Bin , Qin Zhiyan , Wang Song , Liu Huiping , Liu Fengwu . Synthesis and Preliminary Anti-bovine Viral Diarrhea Virus (BVDV) Activity Evaluation of Morpholine Nucleoside Analogues and Their Sulfonamide Derivatives[J]. Chinese Journal of Organic Chemistry, 2018 , 38(5) : 1147 -1154 . DOI: 10.6023/cjoc201712017

References

[1] Gao, Y. X.; Hu, J.; Ju, Y. Acta Chim. Sinica 2016, 74, 312(in Chinese). (高玉霞, 胡君, 巨勇, 化学学报, 2016, 74, 312.)
[2] Nie, B.; Jin, C. F.; Zhong, W. H.; Ren, Q. Y.; Zhang, Y. J.; Zhang, J. Chin. J. Org. Chem. 2017, 37, 2818(in Chinese). (聂飚, 金传飞, 钟文和, 任青云, 张英俊, 张霁, 有机化学, 2017, 37, 2818.)
[3] Ilardi, E. A.; Vitaku, E.; Njardarson, J. T. J. Med. Chem. 2014, 57, 2832.
[4] Wulf, N. R.; Matuszewski, K. A. Am. J. Health-Syst. Pharm. 2013, 70, 1483.
[5] Gawin, R.; De, C. E.; Naesens, L.; Koszytkowska-Stawinska, M. Bioorg. Med. Chem. 2008, 16, 8379.
[6] Zhang, N.; Tan, C.; Cai, P.; Jiang, Y.; Zhang, P.; Zhao, Y. Tetrahedron Lett. 2008, 49, 3570.
[7] Pattanayak, S.; Paul, S.; Sinha, N. B. S. Nucleosides, Nucleotides Nucleic Acids 2012, 31, 763.
[8] Hickman, D. T.; Sreenivasachary, N.; Lehn, J.-M. Helv. Chim. Acta 2008, 91, 1.
[9] Nicolaou, K. C.; Adsool, V. A.; Hale, C. R. Org. Lett. 2010, 12, 1552
[10] Ermolinski, B. S.; Mikhailov, S. N. Russ. J. Bioorg. Chem. 2000, 26, 429.
[11] Tronchet, J. M. J.; Zsély, M.; Cabrini, D.; Jorand, C.; Barbalat-Rey, F.; Komaromi, I; Ricca, A.; Geoffroy, M. Nucleosides Nucleotides 2006, 12, 615.
[12] Hudson, R. H. E.; Li, G.; Tse, J. Tetrahedron Lett. 2002, 43, 1381.
[13] Paul, S.; Pattanayak, S.; Sinha, S. Tetrahedron Lett. 2014, 55, 1072.
[14] Tichenor, M. S.; Trzupek, J. D.; Kastrinsky, D. B.; Hwang, I.; Shiga, F.; Boger, D. L. J. Am. Chem. Soc. 2006, 128, 15683.
[15] Bialecki, J. B.; Yuan, L. H.; Gong, B. Tetrahedron 2007, 63, 5460.
[16] Wang, X. J.; Hou, M. L.; Chen, L. G.; Meng, Y.; Li, Y. Chemistry 2004, 67, 418(in Chinese). (王晓季, 侯曼玲, 陈立功, 孟祎, 李阳, 化学通报, 2004, 67, 418.)
[17] Li, J.; Lowary, T. L. Org. Lett. 2008, 10, 881.
[18] Vasina, V. A; Korovina, D. Y.; Razin, V. V. Russ. J. Org. Chem. 2016, 52, 932.
[19] Fringuelli, F.; Pizzo, F.; Rucci, M.; Vaccaro, L. J. Org. Chem. 2003, 68, 7041.
[20] Salunkhel, A. M.; Brown, H. C. Tetrahedron Lett. 1995, 36, 7987.
[21] Loos, M. D.; Esch, J. H. V.; Kellogg, R. M.; Feringa, B. L. Tetrahedron 2007, 63, 7285.

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