Editor-in-Chief Hatice Kübra Elçioğlu Vice Editors Levent Kabasakal Esra Tatar Online ISSN 2630-6344 Publisher Marmara University Frequency Bimonthly (Six issues / year) Abbreviation J.Res.Pharm. Former Name Marmara Pharmaceutical Journal
Journal of Research in Pharmacy 2021 , Vol 25 , Issue 3
Naphthoquinone–thiazole hybrids bearing adamantane: Synthesis, antimicrobial, DNA cleavage, antioxidant activity, acid dissociation constant, and drug-likeness
Ayşegül DOĞAN1,Sadin ÖZDEMİR2,Mustafa Serkan YALÇIN3,Hayati SARI4,Yahya NURAL5
1Department of Analytical Chemistry, Faculty of Pharmacy, Hacettepe University, 06100 Ankara, Turkey
2Food Processing Programme, Technical Science Vocational School, Mersin University, 33343 Mersin, Turkey
3Department of Chemistry and Chemical Processing Technologies, Technical Science Vocational School, Mersin University, TR-33343 Mersin, Turkey
4Department of Chemistry, Faculty of Science and Arts, Tokat Gaziosmanpasa University, 60250 Tokat, Turkey
5Department of Analytical Chemistry, Faculty of Pharmacy, Mersin University, 33169 Mersin, Turkey
6Advanced Technology, Research and Application Center, Mersin University, 33343 Mersin, Turkey
DOI : 10.29228/jrp.20 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 cleavage activity at 250 and 500 μg/mL. Additionally, the antioxidant activity of the compounds was assessed based on the radical scavenging effect of the stable DPPH (2,2-diphenyl-1-picrylhydrazyl) free radical and the compounds exhibited acceptable antioxidant activity. The acid dissociation constants (pKa) of the compounds were determined potentiometrically in 30% (v/v) dimethyl sulfoxide–water at an ionic background of 0.1 mol L-1 NaCl, at 25 ± 0.1 °C, and the HYPERQUAD computer program was used to calculate the pKa values from the data obtained from potentiometric titrations. Prediction of the drug-likeness properties of the compounds was performed with the use of the MolSoft website, and the compounds had promising drug-likeness model scores within a range of 1.09–1.56. Keywords : Naphthoquinone; thiazole; adamantane; antimicrobial; antioxidant; DNA cleavage; acid dissociation constant; drug-likeness
Marmara University