Synthesis of 1H-benzoxazine-2,4-diones from heterocyclic anhydrides: evaluation of antioxidant and antimicrobial activities

A facile one-step synthesis of 1H-benzoxazine-2,4-diones from heterocyclic anhydrides and TMSA was described. This paper determines their antimicrobial activity against nine human bacterial pathogens by the broth microdilution method; antioxidant activity by DPPH• inactivation and a ferric-reducing...

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Bibliographic Details
Published in:Química Nova 2014, Vol.37 (8), p.1297-1301
Main Authors: Sarmiento-Sánchez, Juan I., Montes-Avila, Julio, Ochoa-Terán, Adrián, Delgado-Vargas, Francisco, Wilson-Corral, Victor, Díaz-Camacho, Sylvia P., García-Páez, Fernando, Bastidas-Bastidas, Pedro
Format: Article
Language:English
Subjects:
1H-benzoxazine-2,4-dione
antimicrobial activity
antioxidant activity
CHEMISTRY, MULTIDISCIPLINARY
toxicity
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Summary:A facile one-step synthesis of 1H-benzoxazine-2,4-diones from heterocyclic anhydrides and TMSA was described. This paper determines their antimicrobial activity against nine human bacterial pathogens by the broth microdilution method; antioxidant activity by DPPH• inactivation and a ferric-reducing power assay; and toxicity by a brine shrimp, Artemia salina, assay. The 1H-benzoxazine-2,4-dione yields were in the range of 57 to 98%. The novel compound 1H-pyrazino[2,3-][1,3]oxazine-2,4-dione 4c showed the highest antioxidant capacity (DPPH 35.4% and FRAP 0.063 µmol TEs/µmol).
ISSN:1678-7064
DOI:10.5935/0100-4042.20140201