Synthesis and Phytogrowth Properties of Oxabicyclic Analogues Related to Helminthosporin

This investigation describes the synthesis and biological evaluation of a series of oxabicyclic analogues related to the helminthosporins. Four oxabicycles were prepared by [4+3] cycloaddition of an oxyallyl carbocation, generated in situ from 2,4-dibromopentan-3-one, with selected furans. Functiona...

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Detalles Bibliográficos
Autores principales: Barbosa, Luiz Cláudio Almeida, Nogueira, Leonardo Brandão, Álvares Maltha, Célia Regina, Teixeira, Róbson Ricardo, Silva, Antônio Alberto
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Molecular Diversity Preservation International 2009
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6253885/
https://www.ncbi.nlm.nih.gov/pubmed/19127245
http://dx.doi.org/10.3390/molecules14010160
Descripción
Sumario:This investigation describes the synthesis and biological evaluation of a series of oxabicyclic analogues related to the helminthosporins. Four oxabicycles were prepared by [4+3] cycloaddition of an oxyallyl carbocation, generated in situ from 2,4-dibromopentan-3-one, with selected furans. Functional group manipulations of the oxabicyclic architecture generated nine further derivatives. The phytotoxic properties of these oxabicycles were evaluated as their ability to interfere with the growth of Sorghum bicolor and Cucumis sativus seedlings. In both species, the most active compounds were oxabicycles possessing a carbonyl group conjugated with a double bond.

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