As part of a project aimed to design and synthesize potential inhibitors of three enzymes overexpressed in head and neck cancer (2GS2, 1DDF, 1D2Q), five triazole derivatives of lawsone (2-hydroxy-1,4-naphtoquinone) stood out as the most promising in a virtual screening study of an in-house chemical library. Based on this, these five triazoles were synthesized to evaluate their activity against head and neck cancer cell lines. The synthesis was carried out in three steps, as follows. Initially, lawsone propargyl ether was obtained by reacting lawsone with propargyl bromide in alkaline medium. In parallel, the azides were prepared by diazotation of suitably substituted anilines followed by reacting the corresponding diazonium salts with sodium azide. Finally, the azido-alkyne cycloaddition reaction ("click" reaction) between lawsone propargyl ether and the azides provided the triazole derivatives of interest in general good yields. The biological evaluation of these compounds is underway and the results will be presented in due time.