Synthesis, characterization, anti-tuberculosis activity and molecular modeling studies of thiourea derivatives bearing aminoguanidine moiety

•Synthesis of thiourea derivatives as antitubercular agents.•Evaluation of antimycobacterial activity by MABA.•Effective antitubercular agents with low cytotoxicities.•InhA experiments for target investigations.•Computational studies for the drugs’ antitubercular effects. The emergence of drug-resistant Mycobacterium tuberculosis strains has posed a driving demand in the search for more effective treatment regimens for tuberculosis. In the present study, a series of novel thiourea derivatives containing aminoguanidine moiety were synthesized by the reaction of aminoguanidine and various isothiocyanates in an attempt to discern new potent active agents against tuberculosis. The structure of synthesized compounds was characterized by FTIR, 1H-NMR, 13C-NMR and HRMS. The proposed structure of compound BI19 was resolved using single X-ray crystallography. The compounds were tested in vitro against M. tuberculosis H37Rv for antitubercular activity. Some of them have high antimycobacterial action, for instance, BI-17 with a MIC value of 0.78 µM and low cytotoxicity. Furthermore, computational studies and enzyme inhibition experiments were performed to identify the target for the observed antitubercular effects. [Display omitted]