According to the structure‐activity relationships (SAR), we synthesized a series of novel thiourea derivatives based on the dapsone‐naphthoquinone hybrid by the nucleophilic addition reaction of various primary/secondary amines to 2‐[4‐(4‐isothiocyanato‐benzenesulfonyl)‐phenylamino]‐[1,4]naphthoquinone (4). All thiourea derivatives (5 a‐j) were screened for in vitro anticancer activity against human leukemia cell line (K562). Thiourea derivative containing N‐methyl piperazine (5 h) was identified as the most effective molecule with IC50= 5.8±0.55 μM. Antimicrobial activity of thiourea derivatives (5 a–j) was evaluated in vitro against six strains of bacteria (Staphylococcus aureus, Staphylococcus epidermidis, Bacillus subtilis, Escherichia coli, Salmonella enterica and Klebsiella pneumoniae) and a fungus Candida kefyr by the microdilution method. Interestingly, compound 5 h exhibited better antibacterial activity compared with the dapsone as a positive control against S. epidermidis. The molecular docking studies indicated that compound 5 h may act as anticancer agent through the inhibition of Abl kinase and T315I Abl mutant.
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