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Synthesis of 3-furanyl-4,5-dihydroisoxazole Derivatives via Cycloaddition and their Antibacterial Evaluation

[ Vol. 16 , Issue. 3 ]

Author(s):

Gabriela de Andrade Danin Barbosa, Alcino Palermo de Aguiar*, Erika Martins de Carvalho and Joseli Maria da Rocha Nogueira   Pages 364 - 369 ( 6 )

Abstract:


Background: Antimicrobial resistance is a major threat to human health. So this manuscript describes the synthesis of five different 3,5-disubstituted 4,5-dihydroisoxazoles with antimicrobial activity.

Methods: They were obtained from nitrile oxide cycloaddition derived from 2-furaldehyde and 5- nitro-2-furaldehyde to different dipolarophiles (acrylamide, ethyl acrylate and styrene). All heterocycles were isolated (30-50 %) and characterized by FTIR, MS, 1H and 13C NMR, as they were also evaluated against Gram-positive and Gram-negative bacteria.

Results and Conclusion: All products showed bioactivity against all bacteria, however, the heterocycle 3-(5-nitro-2-furanyl)-5-carboxylamide-4,5-dihydroisoxazole (6b) presented the lowest value for the minimum inhibition concentration (MIC - 14 µg/mL).

Keywords:

Cycloaddition, dihydroisoxazole, nitrile oxide, antimicrobial, bioactivity, furaldehyde.

Affiliation:

Department of Chemistry, Military Institute of Engineering, Rio de Janeiro, Department of Chemistry, Military Institute of Engineering, Rio de Janeiro, Fundacao Oswaldo Cruz, FIOCRUZ/Farmanguinhos, Rio de Janeiro, FIOCRUZ/ENSP, Fundacao Oswaldo Cruz, Rio de Janeiro

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