Synthesis and characterization of new types of halogenated and alkylated imidazolidineiminothiones and a comparative study of their antitumor, antibacterial, and antifungal activities

► A series of twenty novel imidazolidineiminothiones with various substituents at N-(1) and N-(3) were synthesized. ► Owing to the significant bioactivity of imidazolidineiminothiones which presumably stems from the iminothione function, in this report we addressed the evaluation of the above series of analogs as potential antitumor, antimicrobial, and antifungal agents that contain a combination of pharmacophores of the former compounds and variants at N-(1) and N-(3). ► A comparative study of activity within each group illustrated the effect exerted by the N-(3) substituent, whereas a parallel study of activity for a given substituent throughout the five groups shed light on the role played by the N-(1) substituent. ► Structure-activity relationship study revealed synergistic and opposing effects between the N-(1) and N-(3) substituents which will ultimately assist in the design of highly active derivatives.