First, mono N-Boc diazacycles were introduced onto precursor 1a through a pallado-catalyzed Buchwald-Hartwig coupling, leading to compounds 12a-e in excellent yields. After a quantitatively acidic deprotection of N-Boc moieties, the reductive amination of salts 13a-e in the presence of NaBH(OAc)3 afforded the corresponding 1,4-dimethoxynaphthalene derivatives 14aa to 14f with yields ranging from 29 to 86%. Finally, these compounds were treated with a BCl3 solution in the presence of TBAI giving their oxidized analogues 15aa-f with good yields. In order to assess the influence of each fragment, and in particular the presence or absence of a given (hetero)aromatic or aliphatic motif carried by piperazine, on the structure-activity relationships several reference molecules were designed. The latter are structurally composed of a 6-or 7-membered diazacycle (piperazine or analogue) as well as an N-H or N-Boc unit instead of an N-alkyl one.