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Elsevier4
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PERGAMON-ELSEVIER SCIENCE LTD3
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7th International Eurasian Conference on Biological and Chemical Sciences (EurasianBioChem 2024)2
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WILEY-V C H VERLAG GMBH2
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2nd International Conference on Engineering, Natural and Social Sciences ICENSOS1
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4th International Eurasian Conference on Biological and Chemical Sciences (EurasianBioChem 2021)1
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5th International Eurasian Conference on Biological and Chemical Sciences (EurasianBioChem 2022)1
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ELSEVIER1
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ELSEVIER SCIENCE INC1
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Turkish Chemical Society1
Determination of Formation Constants of Some Metal Complexes of Naphthoquinone Derivatives
Efeoglu, Cagla | Kocagöz, Gülçin | Nural, Yahya | Dincer Kaya, Fadime Nazlı
2025-12-29
New naphthoquinone thiazole hybrids as carbonic anhydrase and cholinesterase inhibitors: Synthesis, crystal structure, molecular docking, and acid dissociation constant
Efeoglu, Cagla | Selcuk, Ozge | Demir, Bunyamin | Nural, Yahya
In this study, N-[3-(3-amino-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-R-thiazol-2(3H)-ylidene]-2,6-difluorobenzamide derivatives as new 1,4-naphthoquinone thiazole hybrids were synthesized by reacting of N-[(3amino-1,4-dioxo-1,4-dihydronaphthalen-2-yl)carbamothioyl]-2,6-difluorobenzamide with various alpha-bromoketones in 76-92% yields. Their molecular structures were characterized by 1H NMR, 13C NMR, 19F NMR, FT-IR, and HRMS, and the stereochemistry of one of the hybrids was determined by single crystal x-ray diffraction study. These synthesized new compounds (3a-e) were found to be effective inhibitor molecules for cholinesterases (butyrylcholinesterase (BChE) and acetylcholinesterase (AChE)), and carbonic anhydrase I and II (hCA I and hCA II) enzymes. KI values were found to be in the ra...
Synthesis of novel immunomodulatory 1,4-disubstituted bis-1,2,3-triazoles by using click chemistry and their intracellular mechanism of action
Nural, Yahya | Acar, Irem | Yetkin, Derya | Efeoglu, Cagla | Ayaz, Furkan
In this study, six new 1,4-disubstituted bis-1,2,3-triazole compounds, N,N '-(1,2-phenylene)bis(2-(4-R-1H-1,2,3triazol-1-yl)acetamide), were synthesized with high yield (88-96 %) by using click chemistry and their molecular structures were characterized by using NMR, FT-IR, HRMS and elemental analysis techniques. Previous studies suggest anti-inflammatory and analgesic activities for different 1,2,3-triazole derivatives and in the light of those studies we aimed to examine these novel derivatives immunomodulatory activities on the mammalian macrophages. Pro-inflammatory cytokines (TNF, IL6, GMCSF and IL12p40) secretion levels were tested in the presence of bis-1,2,3-triazole compounds when the macrophages were activated with LPS. These new derivatives were able to suppress the product...
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...
Synthesis of acylthiourea derivatives and their acid dissociation constants
Efeoglu, Cagla | Karasu, Elize | Nural, Yahya
2025-12-31
Synthesis of Bis-Thiourea Derivatives and Their Acid Dissociation Constants
Efeoglu, Cagla | Tiken, Şit | Nural, Yahya
2025-12-31
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 thiazole urea hybrids bearing morpholine/piperazine: synthesis, crystal structure, aldose reductase and α-glycosidase enzyme inhibition, molecular docking, and electrochemical interaction with dsDNA
Efeoglu, Cagla | Nural, Yahya
In this study, new 1,4-naphthoquinone thiazole urea hybrids bearing morpholine (3a-d) or piperazine (3e-h) moiety were synthesized in 76-89 % yields and characterized by 1H NMR, 13C NMR, FT-IR, HRMS, and elemental analysis. The stereochemistry of 3d was determined by single crystal x-ray diffraction study. We evaluated the inhibitory potential of these compounds 3a-h on aldose reductase (ALR2) and alpha-glycosidase enzyme (alpha-GLY) activity. Our results indicate that these compounds substantially inhibit ALR2 at micromolar doses, with inhibition constants (KIs) between 0.79 and 2.20 mu M and inhibit alpha-GLY KI between 0.67 and 2.82 mu M. Molecular docking simulations were utilized to elucidate inhibitory effects and establish structure-activity relationships for the synthesized compoun...
Anti-inflammatory Potential of 1,4-Naphthoquinone Acyl Thiourea Hybrids on Lipopolysaccharide-Activated Mammalian Macrophages, and Their Acid Dissociation Constants
Canatar, Ceren | Türkben, Havva | Efeoglu, Cagla | Karasu, Elize | Nural, Yahya | Ayaz, Furkan
In this study, seven new and known 1,4-naphthoquinone acyl thiourea hybrids were synthesized and their molecular structures were confirmed by various analytical methods. These derivatives were tested for their anti-inflammatory potential on the murine macrophages. Pro-inflammatory cytokine production levels and cell viabilities were compared between the groups and with LPS positive control groups to determine the most potent anti-inflammatory drug candidate. Our results suggest that these derivatives had anti-inflammatory activity without exerting major cytotoxicity. Their future evaluation in inflammatory and autoimmune disease settings will be crucial for their possible utilization in the clinical setting. The acid dissociation constants of synthesized hybrids 1-7 were determined potenti...
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, ...
Chemosensor properties of tetrakis-1,2,3-triazole derivatives
Efeoglu, Cagla | Azizi, Nangyallai | Nural, Yahya
2025-12-31
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...
Synthesis and Determination of Acid Dissociation Constants of Bis-Acyl Thiourea Derivatives
Efeoglu, Cagla | Tiken, Şit | Nural, Yahya
N,N'-((dodecane-1,12-diylbis(azanediyl))bis(carbonothioyl))bis(4-nitrobenzamide) 5 and N,N'-((dodecane-1,12-diylbis(azanediyl))bis(carbonothioyl))bis(3-nitrobenzamide) 6 as bis acyl thiourea derivatives were synthesized and their molecular structures were characterized using 1H NMR, 13C NMR, COSY, DEPT, HMQC, FT-IR, and HRMS techniques. The acid dissociation constants (pKa) of the bis-acyl thiourea derivatives 5, 6 were determined potentiometrically and spectrophotometrically. The pKa values of products 5, 6 were determined in 50% (v/v) dimethyl sulfoxide–water hydro-organic solvent in the presence of 0.1 molL1 ionic strength of NaCl and in the acidic medium at 25±0.1 °C, and two pKa values were calculated for each compound with the HYPERQUAD computer program using the data obtai...
New 1,2,3-triazole derivatives as acetylcholinesterase and carbonic anhydrase inhibitors: Synthesis, molecular docking, and solubility
Efeoglu, Cagla | Yabalak, Erdal | Nural, Yahya
In this study, a series of new 1,2,3-triazole derivatives were synthesized in 84-93 % yield using copper-catalyzed azide-alkyne cycloaddition (CuAAC) click chemistry and characterized by 1H/13C NMR, FT-IR, and HRMS analyses. The synthesized compounds (4a-h) were evaluated for their inhibitory activities against human carbonic anhydrase isoforms I and II (hCA I and hCA II) and acetylcholinesterase (AChE), which are clinically relevant targets in neurological and metabolic disorders. Among them, compounds 4f and 4g exhibited the most potent dual inhibitory activities. Compound 4f showed KI values of 144.30 nM for hCA II and 205.10 nM for AChE, while compound 4g exhibited KI values of 239.10 nM for hCA II and 125.90 nM for AChE. These values demonstrate that 4f and 4g are more effective than ...
Synthesis of novel acylthioureas bearing naphthoquinone moiety as dual sensor for high-performance naked-eye colorimetric and fluorescence detection of CN− and F− ions and its application in water and food samples
Nural, Yahya | Karasu, Elize | Efeoglu, Cagla
In this study, six new acylthiourea, bearing naphthoquinone moiety, sensors were synthesized in high yield (88-96%) and characterized using H-1/C-13 NMR, FT-IR and HRMS techniques. All synthesized sensors (4a-f) showed shifts in absorbance and colorimetric changes by CN-, F-, AcO-, and H2PO4-. However, 4e showed a chromogenic different sensitivity response to CN- and F- against competing anions such as AcO- and H2PO4- in DMSO. Furthermore, CN- added 4e showed an increase at the emission intensity and intensive fluorimetric color change was observed in UV-light (lambda ex. 365 nm). All sensors showed chromogenic selectivity towards CN- in aqueous solutions (in DMSO/H2O: 1:1, v/v). Interaction mechanisms between 4e and CN- and F- anions were investigated by experimental studies using various...