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DOI: 10.1055/a-1814-9637
Synthesis and Structure–Activity Relationship Studies of Nicotlactone Analogues as Anti-TMV Agents
This study was financially supported by the Key Research and Development Program of Shaanxi (Program No. 2021NY-140), the Natural Science Basic Research Program of Shaanxi (Program No. 2022JQ-185), the Chinese Universities Scientific Fund (Nos. 2452018318, 2452019189, 2452019197), and the Program for Science & Technology Innovation Team of Shaanxi Province (2020TD-035).
Abstract
The synthesis of the originally proposed structure of (±)-nicotlactone A, a potent antiviral lignan with three continuous chiral centers, is reported in 5 steps from methyl acrylate. The key steps of the synthesis included an In-catalyzed regioselective allylation and a Mn-catalyzed Mukaiyama hydration reaction. Our synthetic strategy also enabled us to get the other three epimers and investigate the structure–activity relationship. The NMR data of the synthesized compounds do not match that of the isolated sample, indicating that the structure of nicotlactone A remains to be reassigned. All the synthetic target compounds were evaluated for their anti-tobacco mosaic virus (anti-TMV) activity. Bioassay results indicated that (±)-8-demethylnicotlactone A displayed similar anti-TMV activity to the commercial agent ningnanmycin, thus being a promising candidate or lead compound for developing novel antiviral agents in crop protection.
Key words
lignan - γ-lactone - Mukaiyama hydration reaction - structural simplification - anti-TMV activitySupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1814-9637.
- Supporting Information
- CIF File
Publikationsverlauf
Eingereicht: 05. März 2022
Angenommen nach Revision: 01. April 2022
Accepted Manuscript online:
01. April 2022
Artikel online veröffentlicht:
10. Mai 2022
© 2022. Thieme. All rights reserved
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