Synthesis, Biological Evaluation, Molecular Docking, and Acid Dissociation Constant of New Bis-1,2,3-triazole Compounds
Nural, Yahya | Ozdemir, Sadin | Yalcin, Mustafa Serkan | Demir, Bunyamin
In this study, new bis-1,2,3-triazole derivatives, N,N '-(1,3-phenylene)bis(2-(4-R-1H-1,2,3-triazol-1-yl)acetamide), were synthesized by copper-catalyzed azide-alkyne cycloaddition click chemistry in 84-96 % yield. A wide range bioactivity screening was performed to determine DNA cleavage, antioxidant, antibacterial and antifungal activities. All of the synthesized bis-1,2,3-triazoles showed excellent DNA cleavage activity and 4 e, bearing 2-bromoethyl moiety as a substituent, was almost degraded all of the plasmid DNA. Molecular docking simulations suggest that the synthesized compounds act as minor groove binders of DNA. The antioxidant activities of the bis-1,2,3-triazoles were determined based on the radical scavenging effect of the stable 2,2-diphenyl-1-picrylhydrazyl (DPPH) free...
Synthesis, Biological Evaluation, Molecular Docking, and Acid Dissociation Constant of New Bis-1,2,3-triazole Compounds
Nural, Yahya | Özdemir, Sadin | Yalçın, Mustafa Serkan | Demir, Bünyamin
In this study, new bis-1,2,3-triazole derivatives, N,N′-(1,3-phenylene)bis(2-(4-R-1H-1,2,3-triazol-1-yl)acetamide), were synthesized by copper-catalyzed azide-alkyne cycloaddition click chemistry in 84–96 % yield. A wide range bioactivity screening was performed to determine DNA cleavage, antioxidant, antibacterial and antifungal activities. All of the synthesized bis-1,2,3-triazoles showed excellent DNA cleavage activity and 4 e, bearing 2-bromoethyl moiety as a substituent, was almost degraded all of the plasmid DNA. Molecular docking simulations suggest that the synthesized compounds act as minor groove binders of DNA. The antioxidant activities of the bis-1,2,3-triazoles were determined based on the radical scavenging effect of the stable 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radic...
Synthesis, anti-inflammatory activity, inverse molecular docking, and acid dissociation constants of new naphthoquinone-thiazole hybrids
Efeoglu, Cagla | Selcuk, Ozge | Celik, Begum | Tumkaya, Ece | Nural, Yahya
hronic Inflammation is associated with various types of diseases that involves pro-inflammatory cytokines like IL-6 and TNF-alpha. High costs and serious side effects of available anti-inflammatory/immunomodulatory drugs led us to design new compounds with promising anti-inflammatory activities. Many drugs and biologically important compounds involve naphthoquinone and thiazole moieties in their core structures. Thereby, here we report the synthesis, characterization and anti-inflammatory activities of new naphthoquinone thiazole hybrids by reaction of naphthoquinone acyl thioureas with various alpha-bromoketone derivatives. The position of NO2 group in one of the phenyl rings of naphthoquinone thiazole hybrids was changed while different substituents were introduced at the para position o...
New bis- and tetrakis-1,2,3-triazole derivatives: Synthesis, DNA cleavage, molecular docking, antimicrobial, antioxidant activity and acid dissociation constants
Nural, Yahya | Özdemir, Sadin | Yalçın, Mustafa Serkan | Demir, Bünyamin
In this study, a series of bis– and tetrakis–1,2,3–triazole derivatives were synthesized using copper-catalyzed azide-alkyne cycloaddition (CuAAC) click chemistry in 73–95% yield. The bis– and tetrakis–1,2,3–triazoles exhibited significant DNA cleavage activity while the tetrakis–1,2,3–triazole analog 6g completely degraded the plasmid DNA. Molecular docking simulations suggest that compound 6g acts as minor groove binder of DNA by binding through several noncovalent interactions with base pairs. All bis- and tetrakis–1,2,3-triazole derivatives were screened for antibacterial activity against E. coli, B. cereus, S. aureus, P. aeruginosa, E. hirae, L. pneumophila subsp. pneumophila strains and antifungal activity against microfungus C. albicans and C. tropicalis strains. Compound 4d exhibit...
New bis-and tetrakis-1, 2, 3-triazole derivatives: Synthesis, DNA cleavage, molecular docking, antimicrobial, antioxidant activity and acid dissociation constants
Nural, Yahya | Ozdemir, Sadin | Yalcin, Mustafa Serkan | Demir, Bunyamin
In this study, a series of bis- and tetrakis-1,2,3-triazole derivatives were synthesized using copper-catalyzed azide-alkyne cycloaddition (CuAAC) click chemistry in 73-95% yield. The bis- and tetrakis-1,2,3-triazoles exhibited significant DNA cleavage activity while the tetrakis-1,2,3-triazole analog 6g completely degraded the plasmid DNA. Molecular docking simulations suggest that compound 6g acts as minor groove binder of DNA by binding through several noncovalent interactions with base pairs. All bis- and tetrakis-1,2,3-triazole derivatives were screened for antibacterial activity against E. coli, B. cereus, S. aureus, P. aeruginosa, E. hirae, L. pneumophila subsp. pneumophila strains and antifungal activity against microfungus C. albicans and C. tropicalis strains. Compound 4d exhibit...
Synthesis of New Bis-1,2,3-Triazoles Possessing High Anti-Proliferative Activities and Electrochemical Interaction Studies With dsDNA
Efeoglu, Cagla | Nural, Yahya
In this study, new bis-1,2,3-triazole derivatives (4a–h) were synthesized with 60%–95% yield by reacting N,N'-(4,5-dichloro-1,2-phenylene)bis(2-azidoacetamide) with various alkyne compounds in the presence of CuSO4.5H2O and sodium ascorbate. The in vitro anti-proliferative activity of the products was evaluated against prostate (PC3 cells) and breast cancer (SKBR3 cells), along with normal retinal pigment epithelial ARPE-19 cells to assess their cytotoxic effects. 4e, 4f, and 4a showed notable anti-proliferative activities against PC3 cells, with IC50 values of 10.89, 12.49, and 36.13 µM, respectively, while the reference drug cisplatin showed anti-proliferative activity with IC50 value of 10.5 µM. 4e also showed remarkable anti-proliferative activity compared with the reference drug ...
1,4-Naphthoquinone thiazoles: Synthesis, crystal structure, anti-proliferative activity, and inverse molecular docking study
Efeoglu, Cagla | Demir, Bunyamin | Yabalak, Erdal | Nural, Yahya
In this study, 1,4-naphthoquinone thiazole hybrids were synthesized by reacting 1,4-naphthoquinone thioureas with various alpha-bromoketones in 78-86 % yields and characterized using 1H NMR, 13C NMR, FT-IR, and HRMS techniques. Furthermore, single crystal x-ray diffraction studies were also performed for 3b and 3c hybrids to determine stereochemistry. Density Functional Theory (DFT) calculations were performed to obtain additional information and to support the x-ray studies. The in vitro anti-proliferative activities of 1,4-naphthoquinone thiazoles were investigated against PC3 human prostate cancer cells. The products 3a-h showed antiproliferative activity against PC3 cells, and the cell viability studies showed that the IC50 values of compounds 3f and 3e were 20.10 mu M and 21.14 mu M, ...
Novel urea-thiourea hybrids bearing 1,4-naphthoquinone moiety: Anti-inflammatory activity on mammalian macrophages by regulating intracellular PI3K pathway, and molecular docking study
Efeoglu, Cagla | Yetkin, Derya | Nural, Yahya | Ayaz, Furkan
In this study, four novel urea-thiourea hybrids bearing 1,4-naphthoquinone moiety were synthesized by the reaction of 2,3-diaminonaphthalene-1,4-dione and various isothiocyanate derivatives in 75-88% yield, and their molecular structures were characterized by using H-1/C-13 NMR, FT-IR and HRMS techniques. Urea-thiourea hybrids have been known for their anti-inflammatory activities. Therefore, in our study, we aimed to decipher their biological activities on mammalian macrophages. Macrophages were stimulated by LPS and pro-inflammatory TNF, IL6, GMCSF and IL12p40 cytokine production levels were measured in the presence of these derivatives by ELISA. Our results suggest that these derivatives on stimulated mammalian macrophages had anti-inflammatory activities. In order to examine their intr...
Novel urea-thiourea hybrids bearing 1,4-naphthoquinone moiety: Anti-inflammatory activity on mammalian macrophages by regulating intracellular PI3K pathway, and molecular docking study
Efeoglu, Cagla | Yetkin, Derya | Nural, Yahya | Ayaz, Furkan
In this study, four novel urea-thiourea hybrids bearing 1,4-naphthoquinone moiety were synthesized by the reaction of 2,3-diaminonaphthalene-1,4-dione and various isothiocyanate derivatives in 75-88% yield, and their molecular structures were characterized by using H-1/C-13 NMR, FT-IR and HRMS techniques. Urea-thiourea hybrids have been known for their anti-inflammatory activities. Therefore, in our study, we aimed to decipher their biological activities on mammalian macrophages. Macrophages were stimulated by LPS and pro-inflammatory TNF, IL6, GMCSF and IL12p40 cytokine production levels were measured in the presence of these derivatives by ELISA. Our results suggest that these derivatives on stimulated mammalian macrophages had anti-inflammatory activities. In order to examine their intr...
1,4-Naphthoquinone thiazoles: Synthesis, crystal structure, anti-proliferative activity, and inverse molecular docking study
Efeoğlu, Çağla | Demir, Bünyamin | Yabalak, Erdal | Nural, Yahya
In this study, 1,4-naphthoquinone thiazole hybrids were synthesized by reacting 1,4-naphthoquinone thioureas with various α-bromoketones in 78–86 % yields and characterized using 1H NMR, 13C NMR, FT-IR, and HRMS techniques. Furthermore, single crystal x-ray diffraction studies were also performed for 3b and 3c hybrids to determine stereochemistry. Density Functional Theory (DFT) calculations were performed to obtain additional information and to support the x-ray studies. The in vitro anti-proliferative activities of 1,4-naphthoquinone thiazoles were investigated against PC3 human prostate cancer cells. The products 3a–h showed anti-proliferative activity against PC3 cells, and the cell viability studies showed that the IC50 values of compounds 3f and 3e were 20.10 µM and 21.14 µM, respect...