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

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

doi:10.1007/s11030-024-10849-1

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

Mol Divers. 2024 Apr 29. doi: 10.1007/s11030-024-10849-1. Online ahead of print.

Authors

Xiaoyu Liu^{1

2}, Hongwei Yang^{1

2}, Yaru Sun^{1

2}, Yuting Huang^{1

2}, Shuang Hong^{1

2}, Haolin Yuan^{1

2}, Wei Gao^{1

2}, Liangfu Tang^{3

4}, Zhijin Fan^{5

6}

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.
² Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, Tianjin, 300071, People's Republic of China.
³ State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, No. 94, Weijin Road, Tianjin, 300071, People's Republic of China. lftang@nankai.edu.cn.
⁴ Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, Tianjin, 300071, People's Republic of China. lftang@nankai.edu.cn.
⁵ State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, No. 94, Weijin Road, Tianjin, 300071, People's Republic of China. fanzj@nankai.edu.cn.
⁶ Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, Tianjin, 300071, People's Republic of China. fanzj@nankai.edu.cn.

PMID: 38679675
DOI: 10.1007/s11030-024-10849-1

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.

Keywords: Benzothiadiazole; COI1; Molecular design; Plant elicitor; Quinoline; Synthesis; Systemic acquired resistance activity; Virtual screening.

Abstract

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