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In this work, 2-alkyl-10-chloro-1,2,3,4-tetrahydrobenzo[<i>b</i>][1,6]naphthyridines were obtained and their reactivity was studied. Novel derivatives of the tricyclic scaffold, including 1-phenylethynyl (<b>5</b>), 1-indol-3-yl (<b>8</b>), and azocino[4,5-<i>b</i>]quinoline (<b>10</b>) derivatives, were synthesized and characterized herein for the first time. Among the newly synthesized derivatives, <b>5c</b>–<b>h</b> proved to be MAO B inhibitors with potency in the low micromolar range. In particular, the 1-(2-(4-fluorophenyl)ethynyl) analog <b>5g</b> achieved an IC₅₀ of 1.35 μM, a value close to that of the well-known MAO B inhibitor pargyline.