Synthesis of 3-furanyl-4,5-dihydroisoxazole Derivatives via Cycloaddition and their Antibacterial Evaluation
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Published:2019-01-15
Issue:3
Volume:16
Page:364-369
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ISSN:1570-1808
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Container-title:Letters in Drug Design & Discovery
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language:en
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Short-container-title:LDDD
Author:
de Andrade Danin Barbosa Gabriela1, de Aguiar Alcino Palermo1, de Carvalho Erika Martins2, da Rocha Nogueira Joseli Maria3
Affiliation:
1. Department of Chemistry, Military Institute of Engineering, Rio de Janeiro, Brazil 2. Fundacao Oswaldo Cruz, FIOCRUZ/Farmanguinhos, Rio de Janeiro, Brazil 3. FIOCRUZ/ENSP, Fundacao Oswaldo Cruz, Rio de Janeiro, Brazil
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.
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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.
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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).
Publisher
Bentham Science Publishers Ltd.
Subject
Drug Discovery,Pharmaceutical Science,Molecular Medicine
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