Back to Search
Start Over
Design, synthesis, and biological activities of arecoline derivatives containing 1,3,4-oxadiazole structure.
- Source :
-
Bioorganic chemistry [Bioorg Chem] 2024 Oct; Vol. 151, pp. 107708. Date of Electronic Publication: 2024 Aug 08. - Publication Year :
- 2024
-
Abstract
- Pesticides play an important role in the development of agriculture, as they can prevent and control crop diseases and pests, improve crop yield and quality. However, the abuse and improper use of pesticides can lead to negative impacts such as environmental pollution and pest resistance issues. There is an urgent need to develop green, safe, and efficient pesticides. In this work, natural product arecoline was selected as parent structure, a series of arecoline derivatives were designed, synthesized, and systematically investigated antiviral activities against tobacco mosaic virus (TMV). These compounds were found to have good to excellent anti-TMV activities for the first time. The antiviral activities of 4a, 4 h, 4 l, 4p, 6a, 6c, and 6f are higher than that of ningnanmycin. Compounds 4 h (EC <subscript>50</subscript> value 146 µg/mL) and 4p (EC <subscript>50</subscript> value 161 µg/mL) with simple structures and excellent activities emerged as new antiviral candidates. We chose 4 h to further investigate the antiviral mechanism, which revealed that it can cause virus fragmentation by acting on the viral coat protein (CP). We further validated this result through molecular docking. These compounds also displayed broad-spectrum fungicidal activities against 8 plant pathogenic fungi. This work lays the theoretical foundation for the application of arecoline derivatives in the agricultural field.<br />Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.<br /> (Copyright © 2024 Elsevier Inc. All rights reserved.)
- Subjects :
- Structure-Activity Relationship
Molecular Structure
Dose-Response Relationship, Drug
Microbial Sensitivity Tests
Molecular Docking Simulation
Tobacco Mosaic Virus drug effects
Antiviral Agents pharmacology
Antiviral Agents chemistry
Antiviral Agents chemical synthesis
Oxadiazoles chemistry
Oxadiazoles pharmacology
Oxadiazoles chemical synthesis
Drug Design
Arecoline pharmacology
Arecoline chemical synthesis
Arecoline chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1090-2120
- Volume :
- 151
- Database :
- MEDLINE
- Journal :
- Bioorganic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 39133973
- Full Text :
- https://doi.org/10.1016/j.bioorg.2024.107708