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Volume 27, Issue 19
  • ISSN: 1386-2073
  • E-ISSN: 1875-5402

Abstract

Background

Developing high-efficiency and low-risk small-molecule green fungicide is the key to effective control of the plant pathogenic oomycetes. Indole is an important raw material for drug synthesis. Due to its unique structural skeleton, indole, and its derivatives have exhibited a wide range of biological activities. However, a study on the synthesis of novel indole derivatives as fungicidal agents against has not yet been reported.

Methods

The important intermediates and were synthesized in high yields by Vilsmeier-Haack and Knoevenagel reactions with indole as the lead compound. Furthermore, different substituted benzenesulfonyl groups were introduced into the NH position of the indole ring, and twelve indole derivatives () were prepared. Their structures were well characterized by 1H NMR, HRMS, and melting point.

Results

The results showed that 2-[(-(4-nitrobenzenesulfonyl)-indole-3)-methylene]-diethyl malonate () and 2-[(-(4-nitrobenzenesulfonyl)-5-cyanoindole-3)-methylene]-diethyl malonate () showed more anti-oomycete activity against than the commercialized fungicide zoxamide, with corresponding EC values of 26.53, 23.48 and 28.16 mg/L, respectively, and the protective effect of the compounds against further confirmed the above results.

Conclusion

The preliminary structure-activity relationship showed that the formyl group modification at the C-3 position of the indole ring was acceptable, and the different anti-oomycete activities of R1 and R2 were significantly different, with R1 being 5-CN > H > 6-Me, and R2 being 4-NO > 3-NO, H > 4-Me.

© 2024 Bentham Science Publishers
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2024-12-01
2024-11-26

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Combinatorial Synthesis of Indole Derivatives as Anti-oomycetes Agents
Comb Chem High Throughput Screen 27, 2816 (2024); https://doi.org/10.2174/0113862073252234231017062643
/content/journals/cchts/10.2174/0113862073252234231017062643
/content/journals/cchts/10.2174/0113862073252234231017062643
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  • Article Type:     Research Article
Keyword(s): anti-oomycete activity; indole derivatives; indole synthesis; Natural product; Phytophthora capsici; plant secondary metabolites

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