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Open AccessArticle

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

Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza University of Rome, P.le A. Moro 5, 00185 Rome, Italy
Department of Pharmacy, “G. D’Annunzio” University of Chieti-Pescara, Via dei Vestini 31, 66100 Chieti, Italy
Department of Pharmacy, Università di Pisa, via Bonanno 6, 56126 Pisa, Italy
Centro nazionale per il controllo e la valutazione dei farmaci, Istituto Superiore di Sanità, Viale Regina Elena 299, 00161 Rome, Italy
Pharmaceutical Chemistry, School of Pharmacy and Centre of Excellence for Pharmaceutical Sciences, North-West University, Potchefstroom 2520, South Africa
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Molecules 2019, 24(3), 484;
Received: 28 December 2018 / Revised: 24 January 2019 / Accepted: 27 January 2019 / Published: 29 January 2019
(This article belongs to the Special Issue Trends in the Development of Enzyme Inhibitors)
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. View Full-Text
Keywords: pyrazoline; monoamine oxidase; enantioseparation; molecular modelling; prenyl pyrazoline; monoamine oxidase; enantioseparation; molecular modelling; prenyl
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Guglielmi, P.; Carradori, S.; Poli, G.; Secci, D.; Cirilli, R.; Rotondi, G.; Chimenti, P.; Petzer, A.; Petzer, J.P. 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. Molecules 2019, 24, 484.

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