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Design, synthesis and systemic acquired resistance of 2-benzothiadiazolylquinoline-4-carboxamides by COI1 based virtual screening

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Abstract

Coronatine-insensitive 1 (COI1) has been identified as a target receptor of plant elicitor coronatine (COR). To discover novel plant elicitor leads, most of the potential molecules among 129 compounds discovered from the ZINC database by docking based virtual screening targeting COI1 were quinoline amides. On this lead basis, 2-benzothiadiazolylquinoline-4-carboxamides were rationally designed and synthesized for bioassay. All target compounds did not show significantly in vitro antifungal activity, compounds 4d, 4e and 4o displayed good in vivo systemic acquired resistance activity for Arabidopsis thaliana against Hyaloperonospora arabidopsidis isolate Noco2 with over 80% of inhibitory rate at the concentration of 50 μM. These results indicate that 2-benzothiadiazolylquinoline-4-carboxamides are promising plant elicitor leads for further study.

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Acknowledgements

This study was supported in part by the National Key Research & Development Program of China (2022YFD1700400 and 2022YFD1700402) and the Frontiers Science Center for New Organic Matter, Nankai University (no. 63181206).

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Authors and Affiliations

  1. State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, No. 94, Weijin Road, Tianjin, 300071, People’s Republic of China

    Xiaoyu Liu, Hongwei Yang, Yaru Sun, Yuting Huang, Shuang Hong, Haolin Yuan, Wei Gao, Liangfu Tang & Zhijin Fan

  2. Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, Tianjin, 300071, People’s Republic of China

    Xiaoyu Liu, Hongwei Yang, Yaru Sun, Yuting Huang, Shuang Hong, Haolin Yuan, Wei Gao, Liangfu Tang & Zhijin Fan

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  1. Xiaoyu Liu
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Contributions

X. L., H. Y.(Hongwei Yang) and W. G. finished Docking Based Virtual Screening (DBVS); X. L., Y. S. and Y. H.designed the targrt compounds based molecular docking; X. L., Y. S. and S. H. synthesized the target compounds; X. L., H. Y.(Hongwei Yang), S. H.and H. Y.(Haolin Yuan) finished bioactivity tests; X. L., L. T. and Z. F. wrote the main manuscript; L. T. and Z. F. provided project administration, supervision, and funding acquisition, as well as contributing to writing and reviewing the manuscript. All authors reviewed the manuscript.

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Correspondence to Liangfu Tang or Zhijin Fan.

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Liu, X., Yang, H., Sun, Y. et al. Design, synthesis and systemic acquired resistance of 2-benzothiadiazolylquinoline-4-carboxamides by COI1 based virtual screening. Mol Divers (2024). https://doi.org/10.1007/s11030-024-10849-1

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