Exploring bisbenzimidazole-chalcone hybrid compounds: Dual-action as antibacterial agents targeting biofilm formation and E. coli DNA gyrase inhibition
ADAR ERCAN | ÖKSÜZ ZEHRA | DÖĞEN AYLİN | ALGÜL ÖZTEKİN
The emergence of antibiotic-resistant pathogens has reduced the efficacy of current antimicrobial therapies, emphasizing the need for new therapeutic agents. This study presents the design, synthesis, and evaluation of bisbenzimidazole-chalcone hybrid compounds as potential antimicrobial agents. These compounds were tested for their antimicrobial activity against eleven common pathogens, as well as their ability to inhibit biofilm formation and eradicate preformed biofilms in Escherichia coli. Compounds EA1, EA3, EA4, and EA5 demonstrated antibacterial activity against E. coli comparable to ampicillin (31.25 μg/mL) and outperformed the other tested compounds. Notably, EA4 and EA5 inhibited biofilm formation at sub-MIC concentrations and effectively eradicated preformed biofilms, as ...
New naphthoquinone thiazole hybrids as carbonic anhydrase and cholinesterase inhibitors: Synthesis, crystal structure, molecular docking, and acid dissociation constant
Efeoğlu, Çağla | Selçuk, Özge | Demir, Bünyamin | 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-[(3-amino-1,4-dioxo-1,4-dihydronaphthalen-2-yl)carbamothioyl]-2,6-difluorobenzamide with various α-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 range...
Polysubstituted pyrrolidines linked to 1,2,3-triazoles: Synthesis, crystal structure, DFT studies, acid dissociation constant, drug-likeness, and anti-proliferative activity
İnce, Tuncay | Demir, Bünyamin | Erat, Selma | Nural, Yahya
Novel pyrrolidines linked to 1,2,3-triazole derivatives, dimethyl 1-(2-(4-R-1H-1,2,3-triazol-1-yl)acetyl)-5,5-diphenylpyrrolidine-2,4-dicarboxylate, were synthesized in the presence of sodium ascorbate and copper (II) sulfate pentahydrate by click chemistry in excellent 89–95% yield. The 1H NMR, 13C NMR, DEPT, COSY, HMQC, FT-IR, HRMS and elemental analysis techniques were used for structural characterization. A single crystal X-ray diffraction study was performed in order to determine the stereochemistry of the compounds. The optimization geometry of the compounds was obtained by performing density functional theory. However, the global reactivity parameters were estimated from frontier molecular orbitals. The calculated global reactivity parameters showed that the most reactive compound w...
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...
New naphthoquinone thiazole hybrids as carbonic anhydrase and cholinesterase inhibitors: Synthesis, crystal structure, molecular docking, and acid dissociation constant
Efeoğlu, Çağla | Selçuk, Özge | Demir, Bünyamin | 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-[(3-amino-1,4-dioxo-1,4-dihydronaphthalen-2-yl)carbamothioyl]-2,6-difluorobenzamide with various α-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 range...
Diels Alder reactions The effects of catalyst on the addition reaction
Yılmaz Özgür, Şimşek Kuş Nermin
The reaction between 2,3-dimethyl-1,3-butadiene and dimethyl 7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3dicarboxylate is efficiently achieved with small amounts of catalyst, i.e. phenol, AcOH, nafion, and b cyclodextrin. Exo-diastereoselective cycloaddition reactions were observed both without catalyst and different catalysts for 48 days. As a result, different products (tricyclicmolecule 5, retro-DielseAlder product 6, and oxidation product 7) were obtained with different catalysts. In addition, we synthesized DielseAlders product 8 and tricyclocyclitol 10 via DielseAlder reaction. The structures of these products were characterized by 1H NMR, 13C NMR, MS and IR spectroscopy.