Citation: 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 shu

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

Hua Yingchun ^a,b ,
He Bin ^a,b ,
Qin Zhiyan ^a,b ,
Wang Song ^a,b ,
Liu Huiping ^a,b ,
Liu Fengwu ^a,b,,

a.
School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou 450001
b.
Collaborative Innovation Center of Henan New Drug Research and Safety Evaluation, Zhengzhou 450001

Corresponding author: Liu Fengwu, fwliu@zzu.edu.cn
Received Date: 8 December 2017
Revised Date: 10 January 2018
Available Online: 26 May 2018
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21372207)the National Natural Science Foundation of China 21372207

Figures(3)

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.
- nucleoside analogue,
- morpholine nucleoside,
- sulfonamides derivative,
- anti-BVDV activity
1. [1]
  Gao, Y. X.; Hu, J.; Ju, Y. Acta Chim. Sinica 2016, 74, 312(in Chinese).
2. [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).
3. [3]
  Ilardi, E. A.; Vitaku, E.; Njardarson, J. T. J. Med. Chem. 2014, 57, 2832. doi: 10.1021/jm401375q
4. [4]
  Wulf, N. R.; Matuszewski, K. A. Am. J. Health-Syst. Pharm. 2013, 70, 1483. doi: 10.2146/ajhp120291
5. [5]
  Gawin, R.; De, C. E.; Naesens, L.; Koszytkowska-Stawinska, M. Bioorg. Med. Chem. 2008, 16, 8379. doi: 10.1016/j.bmc.2008.08.041
6. [6]
  Zhang, N.; Tan, C.; Cai, P.; Jiang, Y.; Zhang, P.; Zhao, Y. Tetrahedron Lett. 2008, 49, 3570. doi: 10.1016/j.tetlet.2008.04.035
7. [7]
  Pattanayak, S.; Paul, S.; Sinha, N. B. S. Nucleosides, Nucleotides Nucleic Acids 2012, 31, 763. doi: 10.1080/15257770.2012.724491
8. [8]
  Hickman, D. T.; Sreenivasachary, N.; Lehn, J.-M. Helv. Chim. Acta 2008, 91, 1. doi: 10.1002/(ISSN)1522-2675
9. [9]
  Nicolaou, K. C.; Adsool, V. A.; Hale, C. R. Org. Lett. 2010, 12, 1552 doi: 10.1021/ol100290a
10. [10]
  Ermolinskiĭ, B. S.; Mikhaĭlov, S. N. Russ. J. Bioorg. Chem. 2000, 26, 429. doi: 10.1007/BF02758613
11. [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. [12]
  Hudson, R. H. E.; Li, G.; Tse, J. Tetrahedron Lett. 2002, 43, 1381. doi: 10.1016/S0040-4039(02)00024-2
13. [13]
  Paul, S.; Pattanayak, S.; Sinha, S. Tetrahedron Lett. 2014, 55, 1072. doi: 10.1016/j.tetlet.2013.12.087
14. [14]
  Tichenor, M. S.; Trzupek, J. D.; Kastrinsky, D. B.; Hwang, I.; Shiga, F.; Boger, D. L. J. Am. Chem. Soc. 2006, 128, 15683. doi: 10.1021/ja064228j
15. [15]
  Bialecki, J. B.; Yuan, L. H.; Gong, B. Tetrahedron 2007, 63, 5460. doi: 10.1016/j.tet.2007.04.043
16. [16]
  Wang, X. J.; Hou, M. L.; Chen, L. G.; Meng, Y.; Li, Y. Chemistry 2004, 67, 418(in Chinese). doi: 10.3969/j.issn.0441-3776.2004.06.004
17. [17]
  Li, J.; Lowary, T. L. Org. Lett. 2008, 10, 881. doi: 10.1021/ol703041y
18. [18]
  Vasina, V. A; Korovina, D. Y.; Razin, V. V. Russ. J. Org. Chem. 2016, 52, 932. doi: 10.1134/S1070428016070022
19. [19]
  Fringuelli, F.; Pizzo, F.; Rucci, M.; Vaccaro, L. J. Org. Chem. 2003, 68, 7041. doi: 10.1021/jo034752y
20. [20]
  Salunkhel, A. M.; Brown, H. C. Tetrahedron Lett. 1995, 36, 7987. doi: 10.1016/0040-4039(95)01721-S
21. [21]
  Loos, M. D.; Esch, J. H. V.; Kellogg, R. M.; Feringa, B. L. Tetrahedron 2007, 63, 7285. doi: 10.1016/j.tet.2007.02.066
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