Synthesis of Novel Benzo[b][1,6]naphthyridine Derivatives and Investigation of Their Potential as Scaffolds of MAO Inhibitors

In this work, 2-alkyl-10-chloro-1,2,3,4-tetrahydrobenzo[b][1,6]naphthyridines were obtained and their reactivity was studied. Novel derivatives of the tricyclic scaffold, including 1-phenylethynyl (5), 1-indol-3-yl (8), and azocino[4,5-b]quinoline (10) derivatives, were synthesized and characterized...

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Autores principales: Kulikova, Larisa N., Raesi, Ghulam Reza, Levickaya, Daria D., Purgatorio, Rosa, Spada, Gabriella La, Catto, Marco, Altomare, Cosimo D., Voskressensky, Leonid G.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9962805/
https://www.ncbi.nlm.nih.gov/pubmed/36838649
http://dx.doi.org/10.3390/molecules28041662
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author Kulikova, Larisa N.
Raesi, Ghulam Reza
Levickaya, Daria D.
Purgatorio, Rosa
Spada, Gabriella La
Catto, Marco
Altomare, Cosimo D.
Voskressensky, Leonid G.
author_facet Kulikova, Larisa N.
Raesi, Ghulam Reza
Levickaya, Daria D.
Purgatorio, Rosa
Spada, Gabriella La
Catto, Marco
Altomare, Cosimo D.
Voskressensky, Leonid G.
author_sort Kulikova, Larisa N.
collection PubMed
description In this work, 2-alkyl-10-chloro-1,2,3,4-tetrahydrobenzo[b][1,6]naphthyridines were obtained and their reactivity was studied. Novel derivatives of the tricyclic scaffold, including 1-phenylethynyl (5), 1-indol-3-yl (8), and azocino[4,5-b]quinoline (10) derivatives, were synthesized and characterized herein for the first time. Among the newly synthesized derivatives, 5c–h proved to be MAO B inhibitors with potency in the low micromolar range. In particular, the 1-(2-(4-fluorophenyl)ethynyl) analog 5g achieved an IC(50) of 1.35 μM, a value close to that of the well-known MAO B inhibitor pargyline.
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spelling pubmed-99628052023-02-26 Synthesis of Novel Benzo[b][1,6]naphthyridine Derivatives and Investigation of Their Potential as Scaffolds of MAO Inhibitors Kulikova, Larisa N. Raesi, Ghulam Reza Levickaya, Daria D. Purgatorio, Rosa Spada, Gabriella La Catto, Marco Altomare, Cosimo D. Voskressensky, Leonid G. Molecules Article In this work, 2-alkyl-10-chloro-1,2,3,4-tetrahydrobenzo[b][1,6]naphthyridines were obtained and their reactivity was studied. Novel derivatives of the tricyclic scaffold, including 1-phenylethynyl (5), 1-indol-3-yl (8), and azocino[4,5-b]quinoline (10) derivatives, were synthesized and characterized herein for the first time. Among the newly synthesized derivatives, 5c–h proved to be MAO B inhibitors with potency in the low micromolar range. In particular, the 1-(2-(4-fluorophenyl)ethynyl) analog 5g achieved an IC(50) of 1.35 μM, a value close to that of the well-known MAO B inhibitor pargyline. MDPI 2023-02-09 /pmc/articles/PMC9962805/ /pubmed/36838649 http://dx.doi.org/10.3390/molecules28041662 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Kulikova, Larisa N.
Raesi, Ghulam Reza
Levickaya, Daria D.
Purgatorio, Rosa
Spada, Gabriella La
Catto, Marco
Altomare, Cosimo D.
Voskressensky, Leonid G.
Synthesis of Novel Benzo[b][1,6]naphthyridine Derivatives and Investigation of Their Potential as Scaffolds of MAO Inhibitors
title Synthesis of Novel Benzo[b][1,6]naphthyridine Derivatives and Investigation of Their Potential as Scaffolds of MAO Inhibitors
title_full Synthesis of Novel Benzo[b][1,6]naphthyridine Derivatives and Investigation of Their Potential as Scaffolds of MAO Inhibitors
title_fullStr Synthesis of Novel Benzo[b][1,6]naphthyridine Derivatives and Investigation of Their Potential as Scaffolds of MAO Inhibitors
title_full_unstemmed Synthesis of Novel Benzo[b][1,6]naphthyridine Derivatives and Investigation of Their Potential as Scaffolds of MAO Inhibitors
title_short Synthesis of Novel Benzo[b][1,6]naphthyridine Derivatives and Investigation of Their Potential as Scaffolds of MAO Inhibitors
title_sort synthesis of novel benzo[b][1,6]naphthyridine derivatives and investigation of their potential as scaffolds of mao inhibitors
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9962805/
https://www.ncbi.nlm.nih.gov/pubmed/36838649
http://dx.doi.org/10.3390/molecules28041662
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