Ultrasound-Promoted Synthesis, Structural Characterization and in vitro Antimicrobial Activity of New 5-Aryl-3-(2-hydroxyphenyl)-4,5-dihydro-1H-pyrazole-1-carboximidamides

This work aims the synthesis of amidino pyrazolines by the cyclocondensation reaction between 3-(hetero)aryl-1-(2-hydroxyphenyl)enones and aminoguanidine hydrochloride under sonochemical conditions. Thirteen new compounds were synthesized in 15-83% of yield after sonication for 30 min without purifi...

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Bibliographic Details
Published in:Journal of the Brazilian Chemical Society 2020-04, Vol.31 (4), p.746-755
Main Authors: de Albuquerque, Danilo, Damim, Andressa, Faoro, Eliandro, Casagrande, Gleison, Back, Davi, Moura, Sidnei, de Pereira, Claudio, de Oliveira, Kelly, Pizzuti, Lucas
Format: Article
Language:English
Subjects:
CHEMISTRY, MULTIDISCIPLINARY
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Summary:This work aims the synthesis of amidino pyrazolines by the cyclocondensation reaction between 3-(hetero)aryl-1-(2-hydroxyphenyl)enones and aminoguanidine hydrochloride under sonochemical conditions. Thirteen new compounds were synthesized in 15-83% of yield after sonication for 30 min without purification by chromatography. Furthermore, antimicrobial activities of the synthesized compounds were investigated by in vitro minimum inhibitory concentration (MIC) in a panel of four bacterial strains and four Candida yeasts. As result, the 5-(4-bromophenyl)-3-(2-hydroxyphenyl)-4,5-dihydro-1H-pyrazole-1-carboximidamide hydrochloride was identified as the most active against gram-positive S. aureus and E. faecalis with MIC of 7.8 µg mL−1, similar to the value showed by chloramphenicol, which was used as standard.
ISSN:0103-5053
1678-4790
DOI:10.21577/0103-5053.20190239