To summarize, in this work we report a synthesis of new 1,5-disubstituted pyrrolidin-2-ones 1, 2 via a three-step sequence involving donor-acceptor cyclopropane ring opening with anilines as key step. The 1-aryl-5-styrylpyrrolidin-2-ones 2 were further transformed into tricyclic ring systems 3 using an intramolecular Friedel-Crafts-type cyclization. To our knowledge, biological activity of these compounds, containing the indolizidine scaffold, has not been explored previously in any context. Here we examined the potential of these drugs as a new group of mitostatics. These results establish 5-aryltetrahydropyrrolo[1,2-a]quinoline-1(2H)-ones 3, especially the hit compound 3c, as tubulin polymerization inhibitors, effectively suppressing division of cultured cancer cells. Further modification of the identified scaffold at both phenyl rings and pyrrolidine moiety can provide novel derivatives of 5-aryltetrahydropyrrolo[1,2a]quinoline-1(2H)-one as promising binders to the colchicine site of tubulin.