New tetrahydrobenzo[b][1,6]naphthyridine derivatives: synthesis and biological activity

Microwave-assisted reactions of 10-chlorotetrahydrobenzo[b][1,6]naphthyridines with N-, S-, and C-nucleophiles resulted in the introduction of various structural moieties in position 10 to give new tetrahydrobenzo[b][1,6]naphthyridine derivatives. Substituted 10-phenyl tetrahydrobenzo[b][1,6]naphthyridines were modified at the nitrogen atom of the tetrahydropyridine moiety using activated alkynes. The esterase profile and the antioxidant activity of the obtained compounds were studied. A compound active towards acetylcholinesterase (IC50 = 15.0±0.9 µmol L−1) and a number of compounds selectively inhibiting butyrylcholinesterase (IC50 of up to 17.5±1.4 µmol L−1) were identified. Compounds with a moderate antioxidant activity in ABTS and FRAP assays were found. © Springer Science+Business Media LLC 2025.