Synthesis, biological properties, and acid dissociation constant of novel naphthoquinone–triazole hybrids
Nural, Yahya | Özdemir, Sadin | Demir, Bünyamin | Yalçın, Mustafa Serkan | Erat, Selma
A series of novel 1,4-naphthoquinone–triazole hybrids, N-(3-amino-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-2-(4-R-1H-1,2,3-triazol-1-yl)acetamide, was synthesized by click chemistry in the presence of sodium ascorbate and copper(II) sulfate pentahydrate in 81–94% yield. Various biological properties of the synthesized compounds including DNA binding/cleavage, antioxidant, antibacterial and antifungal properties were evaluated. The DNA binding study was performed using dsDNA and G-quadruplex DNA. All of the compounds showed fluorescence increase in the presence of DNA, regardless of the structure. Up to 2.9 and 2.5 times fluorescence increase upon incubation with double stranded or G-quadruplex DNA was detected for 5f and 5g, respectively. The docking studies performed on dsDNA and G-quadruple...
Novel 1,4-naphthoquinone N-aroylthioureas: Syntheses, crystal structure, anion recognition properties, DFT studies and determination of acid dissociation constants
Gemili, Müge | Nural, Yahya
In this paper, five novel 1,4-naphthoquinone N-aroylthiourea derivatives were synthesized, by the reaction of 2,3-diaminonaphthalene-1,4-dione and aroylisothiocyanates, in excellent yield (88-96%) and characterized by using FT-IR, H-1/C-13 NMR and HRMS. In addition, the molecular structure of one of the 1,4-naphthoquinone N-aroylthiourea compounds was characterized by single crystal X-ray diffraction studies. The absorption spectra of the compounds were determined in DMSO and the dyes have absorption in visible region in the range of 464-477 nm. The chemosensing ability of each of the prepared dyes was assessed by titrating them towards the anions; F-, Cl-, Br-, I- AcO-, CN-, CIO4-, H2PO4-, HSO4-, and NO3-, using spectrophotometric and H-1 NMR titration techniques in DMSO, experimentally. ...
A Review on the Design, Synthesis, and Structure-activity Relationships of Benzothiazole Derivatives against Hypoxic Tumors
Nural, Yahya | Ayaz, Furkan
There has been a growing body of studies on benzothiazoles and benzothiazole derivatives as strong and effective anti-tumor agents against lung, liver, pancreas, breast, and brain tumors. Due to the highly proliferative nature of the tumor cells, the oxygen levels get lower than that of normal tissues in the tumor microenvironment. This situation is called hypoxia and has been associated with increased ability for carcinogenesis. For the drug design and development strategies, the hypoxic nature of the tumor tissues has been exploited more aggressively. Hypoxia itself acts as a signal initiating system to activate the pathways that eventually lead to the spread of the tumor cells into the different tissues, increases the rate of DNA damage, and eventually ends up with more mutation levels ...
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, nonlinear optical properties, photophysical, and theoretical studies of azo dye bearing coumarin-thiophene
Nural Yahya
In this study, three azo dyes bearing coumarin thiophene (6a-c) were synthesized, and their photophysical properties were studied via UV-vis spectroscopy in various solvents. Acidochromic properties were also investigated in DMSO/H2O, and all products showed acidochromic properties. The reversibility studies were carried out to investigate the reusability of the prepared compounds. Furthermore, products 6a-c were also investigated for their potential use as hydroxide sensors. The electric field-induced second harmonic generation (EFISH) technique was used to measure the second-order nonlinear optical properties. The thermal properties of the prepared compounds were investigated via thermogravimetric analysis (TGA). The results showed that the samples are thermally stable up to around 200 d...
New naphthoquinone-imidazole hybrids: Synthesis, anion recognition properties, DFT studies and acid dissociation constants
Nural Yahya
The two new naphthoquinone-imidazole based dyes containing indole and pyrene moiety were synthesized and their molecular structures were confirmed by FT-IR, H-1/C-13 NMR, and HRMS. The anion selectivity and sensitivity of dyes were studied with selected TBA salts in DMSO and binary mixture DMSO:Water (1:1, v/v). These interaction mechanisms were verified by spectrophotometric, spectrofluorometric, and H-1 NMR titration methods. While the both dyes interact with F-, AcO-, CN-, and H2PO4- in DMSO, only CN- interact with dyes in the aqueous solution. In addition, the experimental results were explained by DFT calculations. The acid dissociation constants of the dyes were determined in 25.0 +/- 0.1 degrees C, 0.1 M NaCl ionic strength in 40% (v/v) DMSO-Water aqueous solution, and acid dissocia...
Acyl thiourea derivatives: Versatile tools for chemosensing and heavy metal remediation
Selcuk, Ozge | Nangyallai, Azizi | Nural, Yahya
The increasing environmental pollution, particularly from heavy metals and hazardous anions, poses a significant threat to global health and ecosystems. The unique structural features of these compounds, including multiple coordination sites, enhanced electron density, favorable steric effects, and stabilized metal-ligand complexes, enable their effective application in both chemosensing and heavy metal remediation. As chemosensors, acyl thiourea derivatives exhibit high sensitivity and selectivity in detecting various cations, anions, and neutral species, making them valuable tools for in situ environmental analysis. Additionally, their ability to efficiently adsorb heavy metals like Cu2+, Hg2+, Cd2+, U4+, Pb2+, Pt4+, and Pd2+, along with the removal of Cl− from acidic wastewater, demonst...
Recent advances in the nonlinear optical (NLO) properties of phthalocyanines: A review
Nural Yahya
Phthalocyanines (Pcs) are robust macrocycles dyes, exhibiting high thermal, chemical, and photostability due to the extensive x conjugation. This dye class has found a wide application in numerous fields because of its structural flexibility and the possibility of incorporating various organic and inorganic elements into the Pcs framework. The Pcs also offer the possibility to obtain high-performance materials via the tuning of specific properties. The easiness of synthesis, aromaticity, and structural versatility are the advantages that make Pcs a promising material for numerous applications. This review will focus on recent advances of Pcs for NLO applications.