Novel heterocyclic family of phenyl naphthothiazole carboxamides derived from naphthalimides: synthesis, antitumor evaluation, and DNA photocleavage

A new heterocyclic family of (2-(dimethylamino)ethyl)-2-substituted phenylnaphtho[2,1-d]thiazole-5-carboxamides modified from naphthalimides was designed, synthesized, and quantitatively evaluated as antitumor agents and photonucleases. All these compounds were found to be more cytotoxic against P388 than against A549. B3 (m-NO2) was found to be the strongest inhibitor for P388 with IC50 of 1.49 μM, while B2 was the most cytotoxic compound against A549 with IC50 of 12 μM. B4 (p-CH3), the most efficient DNA photocleaver, showed detectable DNA cleavage at 0.5 μM and total cleavage from form I to 100% form II at 50 μM. The photocleaving mechanism was changed with the modification to be via superoxide anion and radical.

Figure optionsDownload as PowerPoint slide