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Synthesis of novel 1,3,4-oxadiazole derivatives containing diamides as promising antibacterial and antiviral agents

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Abstract

In this paper, a variety of novel 1,3,4-oxadiazole derivatives possessing diamides were synthesized and tested for their antibacterial and antiviral activity. Preliminary antibacterial assays indicated that some intermediates and title compounds displayed excellent inhibition effects against plant pathogens Xanthomonas oryzae pv. oryzae (Xoo) and Xanthomonas axonopodis pv. citri (Xac). Further studies revealed that compound H15 exhibited the strongest activities against Xoo and Xac with minimal EC50 values of 0.7 and 5.9 μg/mL, respectively. Antiviral bioassays suggested that some of these structures displayed appreciable curative activities and moderate protective effects against tobacco mosaic virus (TMV) in vivo. Among them, compound H8 exerted the best chemotherapeutic effect against TMV with the curative rate of 60.0% at 500 µg/mL, which was comparable with those of commercial agricultural antiviral agent ningnanmycin (54.2%). Given their significant biological activities, this kind of compound could serve as new leading compounds in the study of antibacterial and antiviral chemotherapy.

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References

  1. C.M. Hopkins, F.F. White, S.H. Choi, A. Guo, J.E. Leach, Mol. Plant Microbe Interact. 5, 451 (1992)

    Article  CAS  Google Scholar 

  2. B. Li, B.P. Liu, C.L. Shan, M. Ibrahim, Y.H. Lou, Y.L. Wang, G.L. Xie, H.Y. Li, G.S. Sun, Pest Manag. Sci. 69, 312 (2013)

    Article  CAS  Google Scholar 

  3. J.H. Graham, T.R. Gottwald, J. Cubero, A.D.S. Achor, Mol. Plant Pathol. 5, 1 (2004)

    Article  Google Scholar 

  4. X.F. Zhu, Y. Xu, D. Peng, Y. Zhang, T.T. Huang, J.X. Wang, M.G. Zhou, Crop Prot. 47, 24 (2013)

    Article  CAS  Google Scholar 

  5. P. Li, L. Shi, L. Yang, X.W. Chen, F. Wu, Q.C. Shi, W.M. Xu, M. He, D.Y. Hu, B.A. Song, Bioorg. Med. Chem. Lett. 24, 1677 (2014)

    Article  CAS  Google Scholar 

  6. Y. Chen, X. Yang, C.Y. Gu, A.F. Zhang, Y. Zhang, W.X. Wang, T.C. Gao, J. Yao, S.K. Yuan, Ann. Appl. Biol. 166, 129 (2015)

    Article  CAS  Google Scholar 

  7. L.S. Murate, A.G. de Oliveira, A.Y. Higashi, A.R. Barazetti, A.S. Simionato, C.S. da Silva, G.C. Simões, I.M.O. dos Santos, M.R. Ferreira, M.V.T. Cely, M.O.P. Navarro, V.F. de Freitas, M.A. Nogueira, J.C.P. de Mello, R.P.L.G. Andrade Jr., Agric. Sci. 6, 295 (2015)

    Google Scholar 

  8. A. Piazza, T. Zimaro, B.S. Garavaglia, F.A. Ficarra, L. Thomas, C. Marondedze, R. Feil, J.E. Lunn, C. Gehring, J. Ottado, N. Gottig, J. Exp. Bot. 66, 2795 (2015)

    Article  CAS  Google Scholar 

  9. A.G. de Oliveira, L.S. Murate, F.R. Spago, L. de Paula Lopes, J.P. Oliveira Beranger, J.A.B.S. de Martin, M.A. Nogueira, J.C.P. de Mello, C.G.T. de Jesus Andrade, G. Andrade, Biol. Control 56, 125 (2011)

    Article  Google Scholar 

  10. A. Hazra, S. Mondal, A. Maity, S. Naskar, P. Saha, R. Paira, K.B. Sahu, P. Paira, S. Ghosh, C. Sinha, A. Samanta, S. Banerjee, N.B. Mondal, Eur. J. Med. Chem. 46, 2132 (2011)

    Article  CAS  Google Scholar 

  11. H. Khalilullah, M.J. Ahsan, M. Hedaitullah, S. Khan, B. Ahmed, Mini Rev. Med. Chem. 12, 789 (2012)

    Article  CAS  Google Scholar 

  12. P. Li, L. Shi, M. Gao, X. Yang, W. Xue, L.H. Jin, D.Y. Hu, B.A. Song, Bioorg. Med. Chem. Lett. 25, 481 (2015)

    Article  CAS  Google Scholar 

  13. S. Perumalsamy, M. Bharani, M. Sudha, P. Nagarajan, L. Arul, R. Saraswathi, P. Balasubramanian, J. Ramalingam, Plant Breed. 129, 400 (2010)

    CAS  Google Scholar 

  14. M. Wu, G.F. Han, Z.W. Wang, Y.X. Liu, Q.M. Wang, J. Agric. Food Chem. 61, 1030 (2013)

    Article  CAS  Google Scholar 

  15. W.G. Zhao, J.G. Wang, Z.M. Li, Z. Yang, Bioorg. Med. Chem. Lett. 16, 6107 (2006)

    Article  CAS  Google Scholar 

  16. B. Su, C.L. Cai, M. Deng, Q.M. Wang, J. Agric. Food Chem. 64, 2039 (2016)

    Article  CAS  Google Scholar 

  17. Z.W. Wang, P. Wei, L.Z. Wang, Q.M. Wang, J. Agric. Food Chem. 60, 10212 (2012)

    Article  CAS  Google Scholar 

  18. G.Y. Huang, C. Cui, Z.P. Wang, Y.Q. Li, L.X. Xiong, L.Z. Wang, S.J. Yu, Z.M. Li, W.G. Zhao, Chem. Cent. J. 7, 33 (2013)

    Article  Google Scholar 

  19. Z. Li, P. Zhan, X. Liu, Mini Rev. Med. Chem. 11, 1130 (2011)

    Article  CAS  Google Scholar 

  20. X.H. Gan, D.Y. Hu, P. Li, J. Wu, X.W. Chen, W. Xue, B.A. Song, Pest Manag. Sci. 72, 534 (2016)

    Article  CAS  Google Scholar 

  21. Z. Jakopin, M.S. Dolenc, Curr. Org. Chem. 12, 850 (2008)

    Article  CAS  Google Scholar 

  22. C.V. Maftei, E. Fodor, P.G. Jones, M. Freytag, M.H. Franz, G. Kelter, H.-H. Fiebig, M. Tamm, I. Neda, Eur. J. Med. Chem. 101, 431 (2015)

    Article  CAS  Google Scholar 

  23. E. Spink, D.R. Ding, Z.H. Peng, M.A. Boudreau, E. Leemans, E. Lastochkin, W. Song, K. Lichtenwalter, P.I. O’Daniel, S.A. Testero, H.L. Pi, V.A. Schroeder, W.R. Wolter, N.T. Antunes, M.A. Suckow, S. Vakulenko, M. Chang, S. Mobashery, J. Med. Chem. 58, 1380 (2015)

    Article  CAS  Google Scholar 

  24. E. Leemans, K.V. Mahasenan, M. Kumarasiri, E. Spink, D.R. Ding, P.I. O’Daniel, M.A. Boudreau, E. Lastochkin, S.A. Testero, T. Yamaguchi, M. Lee, D. Hesek, J.F. Fisher, M. Chang, S. Mobashery, Bioorg. Med. Chem. Lett. 26, 1011 (2016)

    Article  CAS  Google Scholar 

  25. A. Vaidya, S. Jain, P. Jain, P. Jain, N. Tiwari, R. Jain, R. Jain, A.K. Jain, R.K. Agrawal, Mini Rev. Med. Chem. 16, 825 (2016)

    Article  CAS  Google Scholar 

  26. S.C. Karad, V.B. Purohit, J.R. Avalani, N.H. Sapariya, D.K. Raval, RSC Adv. 6, 41532 (2016)

    Article  CAS  Google Scholar 

  27. Q.Z. Zheng, X.M. Zhang, Y. Xu, K. Cheng, Q.C. Jiao, H.L. Zhu, Bioorg. Med. Chem. 18, 7836 (2010)

    Article  CAS  Google Scholar 

  28. R.A. Rane, S.D. Gutte, N.U. Sahu, Bioorg. Med. Chem. Lett. 22, 6429 (2012)

    Article  CAS  Google Scholar 

  29. A.H. Shridhar, J. Keshavayya, S.K. Peethambar, H.J. Hoskeri, Arab. J. Chem. 9, S1643 (2016)

    Article  CAS  Google Scholar 

  30. S.T. Dhumal, A.R. Deshmukh, M.R. Bhosle, V.M. Khedkar, L.U. Nawale, D. Sarkar, R.A. Mane, Bioorg. Med. Chem. Lett. 26, 3646 (2016)

    Article  CAS  Google Scholar 

  31. B.A. Johns, J.G. Weatherhead, S.H. Allen, J.B. Thompson, E.P. Garvey, S.A. Foster, J.L. Jeffrey, W.H. Miller, Bioorg. Med. Chem. Lett. 19, 1807 (2009)

    Article  CAS  Google Scholar 

  32. P. Neeraja, S. Srinivas, K. Mukkanti, P.K. Dubey, S. Pal, Bioorg. Med. Chem. Lett. 26, 5212 (2016)

    Article  CAS  Google Scholar 

  33. V. Ravichandran, S. Shalini, K. Sundram, A.D. Sokkalingam, Eur. J. Med. Chem. 45, 2791 (2010)

    Article  CAS  Google Scholar 

  34. T. Pal, R.R. Somani, P.Y. Shirodkar, U.V. Bhanushali, Med. Chem. Res. 20, 1550 (2011)

    Article  CAS  Google Scholar 

  35. H. Khalilullah, S. Khan, M.S. Nomani, B. Ahmed, Arab. J. Chem. 9, S1029 (2016)

    Article  CAS  Google Scholar 

  36. F. Benmansour, C. Eydoux, G. Querat, X. de Lamballerie, B. Canard, K. Alvarez, J.C. Guillemot, K. Barral, Eur. J. Med. Chem. 109, 146 (2016)

    Article  CAS  Google Scholar 

  37. C.V. Maftei, E. Fodor, P.G. Jones, C.G. Daniliuc, M.H. Franz, G. Kelter, H.-H. Fiebig, M. Tamm, I. Neda, Tetrahedron 72, 1185 (2016)

    Article  CAS  Google Scholar 

  38. M.S. Behalo, RSC Adv. 6, 103132 (2016)

    Article  CAS  Google Scholar 

  39. Z.B. Yang, D.Y. Hu, S. Zeng, B.A. Song, Bioorg. Med. Chem. Lett. 26, 1161 (2016)

    Article  CAS  Google Scholar 

  40. J.A. Good, J. Silver, C. Núñez-Otero, W. Bahnan, K.S. Krishnan, O. Salin, P. Engström, R. Svensson, P. Artursson, Å. Gylfe, S. Bergström, F. Almqvist, J. Med. Chem. 59, 2094 (2016)

    Article  CAS  Google Scholar 

  41. P. Teng, D. Huo, A. Nimmagadda, J. Wu, F. She, M. Su, X. Lin, J. Yan, A. Cao, C. Xi, Y. Hu, J. Cai, J. Med. Chem. 59, 7877 (2016)

    Article  CAS  Google Scholar 

  42. I. Neda, H.-J. Plinta, A. Fischer, P.G. Jones, R. Schmutzler, J. Fluor. Chem. 71, 65 (1995)

    Article  CAS  Google Scholar 

  43. H.-J. Plinta, I. Neda, R. Schmutzler, Z. Naturforsch. B 49, 100 (1994)

    Article  CAS  Google Scholar 

  44. R. Sonnenburg, I. Neda, A. Fischer, P.G. Jones, R. Schmutzler, Z. Naturforsch. B 49, 788 (1994)

    Article  CAS  Google Scholar 

  45. I. Neda, H.-J. Plinta, R. Schmutzler, Z. Naturforsch. B 48, 333 (1993)

    CAS  Google Scholar 

  46. I. Neda, T. Kaukorat, R. Schmutzler, Phosphorus Sulfur 84, 205 (1993)

    Article  CAS  Google Scholar 

  47. P.Y. Wang, L. Zhou, J. Zhou, Z.B. Wu, W. Xue, B.A. Song, S. Yang, Bioorg. Med. Chem. Lett. 26, 1214 (2016)

    Article  CAS  Google Scholar 

  48. P.Y. Wang, M.N. Gao, L. Zhou, Z.B. Wu, D.Y. Hu, J. Hu, S. Yang, Bioorg. Med. Chem. Lett. 26, 1236 (2016)

    Google Scholar 

  49. X. Wang, J. Yin, L. Shi, G. Zhang, B.A. Song, Eur. J. Med. Chem. 77, 65 (2014)

    Article  CAS  Google Scholar 

  50. W.M. Xu, S.Z. Li, M. He, S. Yang, X.Y. Li, P. Li, Bioorg. Med. Chem. Lett. 23, 5821 (2013)

    Article  CAS  Google Scholar 

  51. Y. Han, Y. Ding, D.D. Xie, D.Y. Hu, P. Li, X.Y. Li, W. Xue, L.H. Jin, B.A. Song, Eur. J. Med. Chem. 92, 732 (2015)

    Article  CAS  Google Scholar 

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Acknowledgements

We acknowledge the financial support of the Key Technologies R&D Program (2014BAD23B01), National Natural Science Foundation of China (21372052, 21662009), the Research Project of Ministry of Education of China (20135201110005), and Scientific and Technological Projects of Guizhou Province [2016]1029.

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Author notes

  1. Pei-Yi Wang and Wu-Bin Shao authors have contributed equally to this work.

Authors and Affiliations

  1. State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Guiyang, 550025, China

    Pei-Yi Wang, Wu-Bin Shao, Hai-Tao Xue, He-Shu Fang, Jian Zhou, Zhi-Bing Wu, Bao-An Song & Song Yang

  2. School of Pharmaceutical Sciences, Guizhou University, Guiyang, 550025, China

    Hai-Tao Xue

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  1. Pei-Yi Wang
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Correspondence to Bao-An Song or Song Yang.

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11164_2017_2980_MOESM1_ESM.docx

NMR spectra (Figure S1-S28) of title compounds; Crystal structure data of compound F ′, this material is available free of charge via the internet at http://www.xxx.com/. (DOCX 1615 kb)

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Wang, PY., Shao, WB., Xue, HT. et al. Synthesis of novel 1,3,4-oxadiazole derivatives containing diamides as promising antibacterial and antiviral agents. Res Chem Intermed 43, 6115–6130 (2017). https://doi.org/10.1007/s11164-017-2980-x

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