New N-acetyl/N-thiocarbamoylpyrazoline derivatives were designed and synthesized in high yields to assess their inhibitory activity and selectivity against human monoamine oxidase A and B. The most important chiral compounds were separated into their single enantiomers and tested. The impact of the substituents at N1, C3 and C5 positions as well the influence of the configuration of the C5 on the biological activity were analyzed. Bulky aromatic groups at C5 were not tolerated. p-Prenyloxyaryl moiety at C3 oriented the selectivity toward the B isoform. The results were also corroborated by molecular modelling studies providing new suggestions for the synthesis of privileged structures to serve as lead compounds for the treatment of mood disorders and neurodegenerative diseases.

Design, synthesis, docking studies and monoamine oxidase inhibition of a small library of 1-acetyl- and 1-thiocarbamoyl-3,5-diphenyl-4,5-dihydro-(1h)-pyrazoles / Guglielmi, Paolo; Carradori, Simone; Poli, Giulio; Secci, Daniela; Cirilli, Roberto; Rotondi, Giulia; Chimenti, Paola; Petzer, Anél; Petzer, Jacobus P.. - In: MOLECULES. - ISSN 1420-3049. - 24:3(2019), pp. 1-21. [10.3390/molecules24030484]

Design, synthesis, docking studies and monoamine oxidase inhibition of a small library of 1-acetyl- and 1-thiocarbamoyl-3,5-diphenyl-4,5-dihydro-(1h)-pyrazoles

Guglielmi, Paolo
Primo
;
Secci, Daniela;ROTONDI, GIULIA;Chimenti, Paola;
2019

Abstract

New N-acetyl/N-thiocarbamoylpyrazoline derivatives were designed and synthesized in high yields to assess their inhibitory activity and selectivity against human monoamine oxidase A and B. The most important chiral compounds were separated into their single enantiomers and tested. The impact of the substituents at N1, C3 and C5 positions as well the influence of the configuration of the C5 on the biological activity were analyzed. Bulky aromatic groups at C5 were not tolerated. p-Prenyloxyaryl moiety at C3 oriented the selectivity toward the B isoform. The results were also corroborated by molecular modelling studies providing new suggestions for the synthesis of privileged structures to serve as lead compounds for the treatment of mood disorders and neurodegenerative diseases.
2019
enantioseparation; molecular modelling; monoamine oxidase; prenyl; pyrazoline;
01 Pubblicazione su rivista::01a Articolo in rivista
Design, synthesis, docking studies and monoamine oxidase inhibition of a small library of 1-acetyl- and 1-thiocarbamoyl-3,5-diphenyl-4,5-dihydro-(1h)-pyrazoles / Guglielmi, Paolo; Carradori, Simone; Poli, Giulio; Secci, Daniela; Cirilli, Roberto; Rotondi, Giulia; Chimenti, Paola; Petzer, Anél; Petzer, Jacobus P.. - In: MOLECULES. - ISSN 1420-3049. - 24:3(2019), pp. 1-21. [10.3390/molecules24030484]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/1237661
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