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

ABSTRACT: 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 IC₅₀ of 1.35 μM, a value close to that of the well-known MAO B inhibitor pargyline.

SUBMITTER: Kulikova LN

PROVIDER: S-EPMC9962805 | biostudies-literature | 2023 Feb

REPOSITORIES: biostudies-literature

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

Kulikova Larisa N LN Raesi Ghulam Reza GR Levickaya Daria D DD Purgatorio Rosa R Spada Gabriella La G Catto Marco M Altomare Cosimo D CD Voskressensky Leonid G LG

Molecules (Basel, Switzerland) 20230209 4

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 pa ...[more]

PMID: 36838649

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