Design, synthesis and structure–activity relationship of phthalimides endowed with dual antiproliferative and immunomodulatory activities

The present work reports the synthesis and evaluation of the antitumour and immunomodulatory properties of new phthalimides derivatives designed to explore molecular hybridization and bioisosterism approaches between thalidomide, thiosemicarbazone, thiazolidinone and thiazole series. Twenty-seven new molecules were assessed for their immunosuppressive effect toward TNFα, IFNγ, IL-2 and IL-6 production and antiproliferative activity. The best activity profile was observed for the (6a–f) series, which presents phthalyl and thiazolidinone groups. [Display omitted] •Twenty-seven compounds showed dual anti-cancer and immunomodulatory activities.•Series (6a–f) show perceptual inhibition range of 32.1–96.8 for SF-295 cell line.•Compounds (6b) and (6f) show better inhibition profile of cancer cell lines than thl.•The functionalization of series 3 to series 6 achieved better anti-cancer profile.