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

Ayşegül Doğan; Sadin Özdemir; Mustafa Serkan Yalçın; Hayati Sarı; Yahya Nural

Makale detayları

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

Yazarlar:

Ayşegül Doğan | Sadin Özdemir | Mustafa Serkan Yalçın | Hayati Sarı | Yahya Nural

Yayıncı:

Marmara University

Ana Başlıklar:

Pharmaceutical Analytical Chemistry | Pharmaceutical Chemistry

Dergi:

Journal of Research in Pharmacy Vol.25 Issue 3, pp.292-304

Belge Tipi:

Makale

Yayın Tarihi:

6/2025

Belge Dili:

İngilizce

Document ID (Org No.):

2001347924

pISSN:

2630-6344

Anahtar kelimeler:

Özet:

 In this study, four novel naphthoquinonethiazole hybrids bearing adamantane were synthesized by reaction of naphthoquinonearoylthiourea derivatives with 1-adamantyl bromomethyl ketone in 75-85 yield and were characterized using 1H13C 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 464 µgmL and antifungal activity against Candida albicans strains with MIC values in the range of 1664 µgmL. The compounds had DNA cleavage activity at 250 and 500 µgmL. 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 vv dimethyl sulfoxidewater 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 1.091.56.

 In this study, four novel naphthoquinonethiazole hybrids bearing adamantane were synthesized by reaction of naphthoquinonearoylthiourea derivatives with 1-adamantyl bromomethyl ketone in 75-85 yield and were characterized using 1H13C 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 464 µgmL and antifungal activity against Candida albicans strains with MIC values in the range of 1664 µgmL. The compounds had DNA cleavage activity at 250 and 500 µgmL. 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 vv dimethyl sulfoxidewater 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 1.091.56.

 In this study, four novel naphthoquinonethiazole hybrids bearing adamantane were synthesized by reaction of naphthoquinonearoylthiourea derivatives with 1-adamantyl bromomethyl ketone in 75-85 yield and were characterized using 1H13C 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 464 µgmL and antifungal activity against Candida albicans strains with MIC values in the range of 1664 µgmL. The compounds had DNA cleavage activity at 250 and 500 µgmL. 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 vv dimethyl sulfoxidewater 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 1.091.56.

 In this study, four novel naphthoquinonethiazole hybrids bearing adamantane were synthesized by reaction of naphthoquinonearoylthiourea derivatives with 1-adamantyl bromomethyl ketone in 75-85 yield and were characterized using 1H13C 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 464 µgmL and antifungal activity against Candida albicans strains with MIC values in the range of 1664 µgmL. The compounds had DNA cleavage activity at 250 and 500 µgmL. 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 vv dimethyl sulfoxidewater 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 1.091.56.

Makale detayları

Yazarlar: Ayşegül Doğan | Sadin Özdemir | Mustafa Serkan Yalçın | Hayati Sarı | Yahya Nural

Yayıncı: Marmara University

Ana Başlıklar: Pharmaceutical Analytical Chemistry | Pharmaceutical Chemistry

Dergi: Journal of Research in Pharmacy Vol.25 Issue 3, pp.292-304

Belge Tipi: Makale

Yayın Tarihi: 6/2025

Belge Dili: İngilizce

Document ID (Org No.): 2001347924

pISSN: 2630-6344

Sayı

Yazarlar:

Ayşegül Doğan | Sadin Özdemir | Mustafa Serkan Yalçın | Hayati Sarı | Yahya Nural

Yayıncı:

Marmara University

Ana Başlıklar:

Pharmaceutical Analytical Chemistry | Pharmaceutical Chemistry

Dergi:

Journal of Research in Pharmacy Vol.25 Issue 3, pp.292-304

Belge Tipi:

Makale

Yayın Tarihi:

6/2025

Belge Dili:

İngilizce

Document ID (Org No.):

2001347924

pISSN:

2630-6344