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 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.