Pyrone Biomonitored Synthesis

Clécio  Souza Ramos; Marcílio Wagner  Fontes Silva

doi:10.29356/jmcs.v69i2.2213

Pyrone Biomonitored Synthesis

Authors

Clécio Souza Ramos Rural Federal University of Pernambuco
Marcílio Wagner Fontes Silva Rural Federal University of Pernambuco https://orcid.org/0000-0002-5914-5402

DOI:

https://doi.org/10.29356/jmcs.v69i2.2213

Keywords:

Yangonin, styrylpyrone, antifungal, antibacterial, antimicrobial, pyrone

Abstract

Abstract. Here we report the first biomonitored synthesis of pyrones in the search for molecules with antimicrobial action against pathogenic bacteria and fungi. Pyrones were synthesized from methyl acetoacetate pyrone rings followed by deacetylation, methylation, and aldol condensation reactions to obtain styrylpyrones with yields between 39 and 93 %. The compounds were characterized based on the interpretation of their UV, IR, MS and ¹H and ¹³C NMR spectra. The reagents and products used in the first step of the reaction exhibited antimicrobial activity against the six microorganisms tested, except for methyl acetoacetate and benzaldehyde, which were inactive against Klebsiella pneumoniae bacteria. The results obtained contribute significantly to the knowledge of the antimicrobial potential of pyrones, considering that pyrone rings are widely used as building blocks in the synthesis of bioactive molecules. This is also the first report of antimicrobial activity for synthesized styrylpyrone.

Resumen. Aquí informamos la primera síntesis biomonitoreada de pironas en la búsqueda de moléculas con acción antimicrobiana contra bacterias y hongos patogénicos. Las pironas se sintetizaron a partir de anillos de pirona de acetoacetato de metilo seguido de reacciones de desacetilación, metilación y condensación aldólica para obtener estirilpironas con rendimientos entre 39 y 93 %. Los compuestos se caracterizaron basándose en la interpretación de sus espectros UV, IR, MS y RMN ¹H y ¹³C. Los reactivos y productos utilizados en el primer paso de la reacción mostraron actividad antimicrobiana contra los seis microorganismos probados, excepto el acetoacetato de metilo y el benzaldehído, que fueron inactivos contra la bacteria Klebsiella pneumoniae. Los resultados obtenidos contribuyen significativamente al conocimiento del potencial antimicrobiano de las pironas, considerando que los anillos de pirona son ampliamente utilizados como componentes básicos en la síntesis de moléculas bioactivas. Este es también el primer informe sobre la actividad antimicrobiana de la estirilpirona sintetizada.

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Author Biographies

Clécio Souza Ramos, Rural Federal University of Pernambuco

Department of Chemistry

Marcílio Wagner Fontes Silva , Rural Federal University of Pernambuco

Department of Chemistry

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