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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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
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CHEMISTRY, MULTIDISCIPLINARY
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container_end_page 755
container_issue 4
container_start_page 746
container_title Journal of the Brazilian Chemical Society
container_volume 31
creator de Albuquerque, Danilo
Damim, Andressa
Faoro, Eliandro
Casagrande, Gleison
Back, Davi
Moura, Sidnei
de Pereira, Claudio
de Oliveira, Kelly
Pizzuti, Lucas
description 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.
doi_str_mv 10.21577/0103-5053.20190239
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title Ultrasound-Promoted Synthesis, Structural Characterization and in vitro Antimicrobial Activity of New 5-Aryl-3-(2-hydroxyphenyl)-4,5-dihydro-1H-pyrazole-1-carboximidamides
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