Citation: Wu Wenneng, Fei Qiang, He Jun, Liu Lei, Ouyang Guiping. Syntheses and Biological Activities of 1, 3, 4-Oxadiazole (Thiadiazole) Thioether Derivatives Containing Pyrimidine Moiety[J]. Chemistry, ;2019, 82(1): 74-79. shu

Syntheses and Biological Activities of 1, 3, 4-Oxadiazole (Thiadiazole) Thioether Derivatives Containing Pyrimidine Moiety

Wu Wenneng ¹ ,
Fei Qiang ¹ ,
He Jun ¹ ,
Liu Lei ¹ ,
Ouyang Guiping ^2,,

1.
Food and Pharmaceutical Engineering Instituted, Guiyang University, Guiyang 550005
2.
School of Pharmaceutical Sciences, Guizhou University, Guiyang 550025

Corresponding author: Ouyang Guiping, oygp710@163.com
Received Date: 7 August 2018
Accepted Date: 27 August 2018

Figures(1)

Based on 4-amino-2-methylpyrimidine-5-carbonitrile as raw material, twelve 2-methyl-5-(5-substitutional-1, 3, 4-oxadiazol/thiadiazole-3-yl)pyrimidin-4-amine compounds were synthesized through five step reactions including hydrolysis, esterification, hydrazidation, cyclization and thioetherification. The structures of titled compounds were characterized by ¹H NMR, ¹³C NMR, MS and elemental analysis. Preliminary bioassay results showed that compounds 6f and 6f' have moderate inhibitory activities against S. sclerotiorum, P. infestans, T. cucumeris and G. zeae at the concerntration of 50 μg/mL, which are comparable to that of Azoxystrobin.
- Pyrimidine,
- 1, 3, 4-Oxadiazol,
- 1, 3, 4-Thiadiazole,
- Fungicide,
- Synthesis
1. [1]
  C V Maftei, E Fodor, P G Jones et al. Eur. J. Med. Chem., 2015, 101: 431~441.
2. [2]
  M Mihorianu, M H Franz, P G Jones et al. Appl. Organomet. Chem., 2016, 30: 581~589.
3. [3]
  K M Dawood, S M Gomha. J. Heterocycl. Chem., 2015, 54(5): 1400~1405.
4. [4]
  R Deshmukh, B Karale, H Akolkar et al. J. Heterocycl. Chem., 2017, 54(2): 1355~1360.
5. [5]
  X H Gan, D Y Hu, Z Chen et al. Bioorg. Med. Chem. Lett., 2017, 18: 4298~4301.
6. [6]
7. [7]
8. [8]
  W M Xu, S Yang, P Bhadury et al. Pestic. Biochem. Phys., 2011, 101: 6~15.
9. [9]
  Z B Yang, D Y Hu, S Zeng et al. Bioorg. Med. Chem. Lett., 2016, 26: 1161~1164.
10. [10]
  X H Liu, Q Wang, Z H Sun et al. Pest Manag. Sci., 2017, 73: 953~959.
11. [11]
  Q Chen, X L Zhu, L L Jiang et al. Eur. J. Med. Chem., 2008, 43: 595~603.
12. [12]
  J Zhang, J F Peng, Y B Bai et al. Mol. Divers., 2016, 20: 887~896.
13. [13]
  Y Zuo, Q Y Wu, S W Su et al. J. Agric. Food Chem., 2016, 64: 552~562.
14. [14]
  X M Chen, S H Wang, D L Cui. J. Heterocycl. Chem., 2015, 52: 607~610.
15. [15]
  S Tang, Z G Peng, X Zhang et al. Chin. Chem. Lett., 2016, 27: 1052~1057.
16. [16]
  X J Xu, J Wang, Q Z Yao. Bioorg. Med. Chem. Lett., 2015, 25: 241~244.
17. [17]
  K Misra, A Nag, A Sonawane. RSC Adv., 2016, 6: 104632~104641.
18. [18]
  S C Karad, B B Purohit, R P Thummar et al. Bioorg. Med. Chem. Lett., 2017, 126: 894~909.
19. [19]
20. [20]
  W N Wu, Q Chen, A Tai et al. Bioorg. Med. Chem. Lett., 2015, 25: 2243~2246.
21. [21]
  W N Wu, M N Gao, H Tu et al. J. Heterocycl. Chem., 2016, 53: 2042~2048.
22. [22]
  W N Wu, AQ Tai, Q Chen et al. J. Heterocycl. Chem., 2015, 53: 626~632.
23. [23]
  K C Tarun, D Prem. J. Agric. Food Chem., 2006, 54(6): 2129~2133.
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