Naphthoquinone–thiazole hybrids bearing adamantane: Synthesis, antimicrobial, DNA cleavage, antioxidant activity, acid dissociation constant, and drug-likeness

Ozdemir, Sadin | Yalçın, Mustafa Serkan | Nural, Yahya

In this study, four novel naphthoquinone–thiazole hybrids bearing adamantane were synthesized by reaction of naphthoquinone–aroylthiourea derivatives with 1-adamantyl bromomethyl ketone in 75-85% yield and were characterized using 1H/13C NMR, FT-IR, and HRMS techniques. Various biological activities of the synthesized compounds, such as antibacterial, antifungal, DNA cleavage, and antioxidant activities, were screened. The compounds showed antibacterial activity against Escherichia coli, Bacillus cereus, Staphylococcus aureus, Pseudomonas aeruginosa, Enterococcus hirae, and Legionella pneumophila subsp. pneumophila strains with MIC values in the range of 4–64 µg/mL and antifungal activity against Candida albicans strains with MIC values in the range of 16–64 µg/mL. The compounds had DNA cl...