Synthesis and fungicidal activity of quinolin-6-yloxyacetamides, a novel class of tubulin polymerization inhibitors

A novel class of experimental fungicides has been discovered, which consists of special quinolin-6-yloxyacetamides. They are highly active against important phytopathogens, such as Phytophthora infestans (potato and tomato late blight), Mycosphaerella graminicola (wheat leaf blotch) and Uncinula nec...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2014-08, Vol.22 (15), p.3922-3930
Main Authors: Lamberth, Clemens, Kessabi, Fiona Murphy, Beaudegnies, Renaud, Quaranta, Laura, Trah, Stephan, Berthon, Guillaume, Cederbaum, Fredrik, Knauf-Beiter, Gertrud, Grasso, Valeria, Bieri, Stephane, Corran, Andy, Thacker, Urvashi
Format: Article
Language:English
Subjects:
Acetamides - chemical synthesis
Acetamides - chemistry
Acetamides - pharmacology
Antifungal Agents - chemical synthesis
Antifungal Agents - chemistry
Antifungal Agents - pharmacology
Crop protection
Fungicide
Heterocycle
Phytophthora infestans - drug effects
Quinoline
Quinolines - chemistry
Saccharomycetales - drug effects
Structure-Activity Relationship
Tubulin
Tubulin Modulators - chemical synthesis
Tubulin Modulators - chemistry
Tubulin Modulators - pharmacology
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Summary:A novel class of experimental fungicides has been discovered, which consists of special quinolin-6-yloxyacetamides. They are highly active against important phytopathogens, such as Phytophthora infestans (potato and tomato late blight), Mycosphaerella graminicola (wheat leaf blotch) and Uncinula necator (grape powdery mildew). Their fungicidal activity is due to their ability to inhibit fungal tubulin polymerization, leading to microtubule destabilization. An efficient synthesis route has been worked out, which allows the diverse substitution of four identified key positions across the molecular scaffold.
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2014.06.015