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Öğe 1Kırıkkale Üniversitesi, Eğitim Fakültesi, Matematik ve Fen Bilimleri Eğitimi Bölümü, Kırıkkale, Türkiye 2İstanbul Gelişim Üniversitesi, Sağlık Bilimleri Yüksekokulu, 34315 Avcılar, İstanbul, Türkiye 3Gen Mühendisliği ve Biyoteknoloji Enstitüsü, Tübitak MAM, 41470, Gebze, Kocaeli, Türkiye(2017) Ökten, Salih; Çakmak, Osman; Tekin, ŞabanAmaç: Bu çalışmada, 6,8-disübstitüe kinolin türevlerinin antikanser potansiyelleri, etki mekanizmaları ve farklı sübstituentlerin aktiviteye etkilerinin belirlemesi amaçlanmıştır.Gereç ve Yöntem: Tetrahidrokinolin molekülü (1), moleküler brom (Br2) ile reaksiyonu ve müteakiben aromatlaştırılması ile 6,8-dibromo-1,2,3,4-tetrahidrokinolin (6,8-dibromoTHQ, 2) ve 6,8-dibromokinolin (6,8-diBrQ, 3) elde edildi. Bu moleküller, yer değiştirme ve Suzuki Kenetleme reaksiyonları sonucu ile 6,8-dimetoksikinolin (6,8-diMeOQ, 4), 6,8-disiyanokinolin (6,8-diCNQ, 6) ve 6,8-difenilkinolin'e (6,8-diPhQ, 5) dönüştürüldü. Sentezlenen bileşiklerin antikanser potansiyellerinin ortaya çıkartmak için HeLa (İnsan rahim kanser hücresi), HT29 (Kolon kanseri) ve C6 (Sıçan beyin kanser hücresi) hücre hatlarına karşı BrDU hücre proliferasyonu, LDH sitotoksisite, DNA bantlaşma ve DNA Topoizomeraz I inhibisyon testleri uygulandı.Bulgular: HT29 hücre hatlarında ise, bileşikler 2, 3, 4 ve 5 numaralı bileşikler hücre proliferasyonunu inhibe etmiştir fakat HeLa ve C6 hücre hatlarında sadece 6,8-dibromoTHQ 2 ve 6,8-diPhQ 5 bileşikleri önemli derecede antiproliferatif etki göstermiştir. 6,8-dibromoTHQ 2, tüm hücre hatlarında yüksek inhibisyon gösterirken, sitotoksik etki göstermemiştir. 6,8-dibromoTHQ 2 DNA bantlaştırma ve Topoizomeraz I enziminin inhibe edebilme özelliği ortaya çıkarılmıştır.Sonuçlar: Kinolin halkasının C-6 ve C-8 konumlarında fonksiyonel grupların değiştikçe farklı aktiviteleri gözlenmiştir. 6,8-DiBrTHQ 2 ve 6,8-diPhQ 5 moleküllerinin antiproliferatif ve apoptotik aktivite göstermeleri sebebiyle antikanser ajan olma potansiyelleri belirlenmiştirÖğe 6,8-disübstitüe kinolin analoglarının anti kanser ajanlar olarak yapı aktivite (SAR) çalışması(2017) Ökten, Salih; Çakmak, Osman; Tekin, ŞabanAmaç: Bu çalışmada, 6,8-disübstitüe kinolin türevlerinin antikanser potansiyelleri, etki mekanizmaları ve farklı sübstituentlerin aktiviteye etkilerinin belirlemesi amaçlanmıştır.Gereç ve Yöntem: Tetrahidrokinolin molekülü (1), moleküler brom (Br2) ile reaksiyonu ve müteakiben aromatlaştırılması ile 6,8-dibromo-1,2,3,4-tetrahidrokinolin (6,8-dibromoTHQ, 2) ve 6,8-dibromokinolin (6,8-diBrQ, 3) elde edildi. Bu moleküller, yer değiştirme ve Suzuki Kenetleme reaksiyonları sonucu ile 6,8-dimetoksikinolin (6,8-diMeOQ, 4), 6,8-disiyanokinolin (6,8-diCNQ, 6) ve 6,8-difenilkinolin'e (6,8-diPhQ, 5) dönüştürüldü. Sentezlenen bileşiklerin antikanser potansiyellerinin ortaya çıkartmak için HeLa (İnsan rahim kanser hücresi), HT29 (Kolon kanseri) ve C6 (Sıçan beyin kanser hücresi) hücre hatlarına karşı BrDU hücre proliferasyonu, LDH sitotoksisite, DNA bantlaşma ve DNA Topoizomeraz I inhibisyon testleri uygulandı.Bulgular: HT29 hücre hatlarında ise, bileşikler 2, 3, 4 ve 5 numaralı bileşikler hücre proliferasyonunu inhibe etmiştir fakat HeLa ve C6 hücre hatlarında sadece 6,8-dibromoTHQ 2 ve 6,8-diPhQ 5 bileşikleri önemli derecede antiproliferatif etki göstermiştir. 6,8-dibromoTHQ 2, tüm hücre hatlarında yüksek inhibisyon gösterirken, sitotoksik etki göstermemiştir. 6,8-dibromoTHQ 2 DNA bantlaştırma ve Topoizomeraz I enziminin inhibe edebilme özelliği ortaya çıkarılmıştır.Sonuçlar: Kinolin halkasının C-6 ve C-8 konumlarında fonksiyonel grupların değiştikçe farklı aktiviteleri gözlenmiştir. 6,8-DiBrTHQ 2 ve 6,8-diPhQ 5 moleküllerinin antiproliferatif ve apoptotik aktivite göstermeleri sebebiyle antikanser ajan olma potansiyelleri belirlenmiştirÖğe Activation of 6-bromoquinoline by nitration: synthesis of morpholinyl and piperazinyl quinolines(Arkat Usa Inc, 2018) Çakmak, Osman; Ökten, Salih; Alimli, Dilek; Saddiqa, Aisha; Ersanlı, Cem CüneytQuinoline forms the key skeletal component of a number of important natural products and pharmacologically-active compounds. Despite a tremendous amount of research pertaining to the derivatization of quinoline, very few general synthetic routes are described in the literature starting from quinoline or tetrahydroquinoline. A simple and convenient method for the polyfunctionalization of quinolines via nitration of bromoquinolines has been developed. This method represents a new synthetic approach to convert brominated nitroquinoline derivatives into useful cyclic amines via nucleophilic-substitution (SNAr) reaction. [GRAPHICS] .Öğe Arylated Quinoline and Tetrahydroquinolines: Synthesis, Characterization and Their Metabolic Enzyme Inhibitory and Antimicrobial Activities(Wiley-V C H Verlag Gmbh, 2022) Kocyigit, Ümit Muhammet; Ökten, Salih; Çakmak, Osman; Burhan, Gizem; Ataş, Mehmet; Taslimi, Parham; Gülçin, İlhamiThe aims of this study are to synthesize and characterize some new phenyl quinoline derivatives and to determine the activities of them and the recently prepared substituted phenyl quinolines against Acetylcholinesterase (AChE) and Charbonic anyhydrase (CA) enzymes and some microorganisms. The 6-phenyl- (3a) and 6,8-diphenyl-(4a) tetrahydroquinolines were prepared by treatment of 6-bromo and 6,8-dibromo-1,2,3,4-tetrahydroquinoline with phenylboronic acids in the presence of Pd catalyze in high yields with respect to our reported procedure. Then, bromination of the 6-phenyl- (3a) and 6,8-diphenyl-(4a) tetrahydroquinolines furnished novel 3-bromo phenyl substituted quinolines 14 and 11 and 8-bromo-6-pheyltetrahydroquinoline (13) in excellent yields (91, 99 and 92 %, respectively). Structures of all prepared compounds were characterized by H-1 NMR,C-13 NMR, FTIR spectroscopy and elemental analysis. Both novel prepared and recent synthesized phenyl substituted tetrahydroquinolines and quinolines were screened for human carbonic anhydrase I, II isoenzymes (hCAs I and II) and AChE inhibitory and antimicrobial activities. Results indicated that all the synthetic compounds exhibited potent inhibitory activities against all targets as compared to the standard inhibitors, revealed by IC50 values. K-i values of novel substituted (trifluoromethoxy, thiomethyl and methoxy) phenyl quinolines 3a-d, 4a-c, 8-12, and 14 for hCA I, hCA II and AChE enzymes were obtained in the ranges 0.31-12.44, 0.92-12.45, and 8.56-27.05 mu M, respectively. Moreover, phenyl quinolines 3a-b, 10, 11, 14 displayed antifungal effect against yeasts in the range of 125-15.62 mu g/mL.Öğe Biological activity and molecular docking studies of some new quinolines as potent anticancer agents(Humana Press Inc, 2021) Köprülü, Tuğba Kul; Ökten, Salih; Atalay, Vildan Enisoglu; Tekin, Şaban; Çakmak, OsmanThe objective of this study is to investigate the antiproliferative and cytotoxic properties and the action mechanism of substituted quinoline and tetrahydroquinolines 3, 4, 5, 7, and 8 against rat glioblastoma (C6), human cervical cancer (HeLa), human adenocarcinoma (HT29) cancer cell lines by BrdU Cell Proliferation ELISA, Lactate Dehydrogenase, DNA laddering and Topoisomerase I assays. The results of the study showed that 6,8-dibromotetrahydroquinoline 3 possess in vitro antiproliferative activity against C6, HeLa, and HT29 cell lines while morpholine/piperazine substituted quinoline 7 and 8 showed selective antiproliferative activity on C6 cell line with IC50 values 47.5 and 46.3 mu g/mL, respectively. Moreover, 6,8-dibromoTHQ 3 caused DNA fragmentation while it did not inhibit the Topoisomerase I (Topo I) enzyme. On the other hand, compound 8 did not cause DNA laddering while 8 inhibited the Topo I enzyme. According to these results, 6,8-dibromoTHQ 3 stimulates apoptosis on the C6 cell line while 6,8-dibromo-3-morhonilylquinoline (8) inhibits the Topo I enzyme to cause antiproliferative activity. Graphic abstractÖğe Biological evaluation of some quinoline derivatives with different functional groups as anticancer agents(Wiley, 2019) Köprülü, Tuğba Kul; Ökten, Salih; Tekin, Şaban; Çakmak, OsmanDue to a great deal of biological activities, quinoline derivatives have drawn attention for synthesis and biological activities in the search for new anticancer drug development. In this work, a variety of substituted (phenyl, nitro, cyano, N-oxide, and methoxy) quinoline derivatives (3-13) were tested in vitro for their biological activity against cancer cell lines, including rat glioblastoma (C6), human cervical cancer cells (HeLa), and human adenocarcinoma (HT29). 6-Bromo-5-nitroquinoline (4), and 6,8-diphenylquinoline (compound 13) showed the greatest antiproliferative activity as compared with the reference drug, 5-fluorouracil (5-FU), while the other compounds showed low antiproliferative activity. 6-Bromo-5-nitroquinoline (4) possesses lower cytotoxic activity than 5-FU in HT29 cell line. Due to its the apoptotic activity 6-Bromo-5-nitroquinoline (4) has the potential to cause cancer cell death.Öğe Bromination and conversion of tetrahydro-1H-indene to bisoxirane with a new approach: synthesis, structural characterization by spectroscopic and theoretical methods, and biological analysis supported by DFT and docking(Tubitak Scientific & Technological Research Council Turkey, 2023) Yılmaz, Raşit Fikret; Erkan, Sultan; Ökten, Salih; Tutar, Ahmet; Şahin, ErtanIn this study, a new method for synthesizing diepoxides is proposed. Tetrahydroindene 1 was brominated with NBS in the presence of LiClO4 and acetic acid, resulting in the formation of dibromodiacetate derivatives 2 and 3. Treatment of compounds 2 and 3 with NaOH in methanol produced a mixture of diepoxides 4 and 5. Additionally, direct bromination of tetrahydro-1H-indene yielded tetrabromo octahydroindene isomers 6 and 7. The structures of the compounds were characterized using spectroscopic techniques such as H-1 NMR, C-13 NMR, APT, COSY, and XRD. The new method provides an easy and selective route to access epoxides for the synthesis of various chemicals. This study also highlights the selective formation of endo-exo and exo-exo orientations of the obtained diepoxides, distinguishing it from previous studies. The stability and properties of the stereoisomers were investigated using computational methods, revealing the most stable configurations. Reactive sites in the molecules were identified using contour diagrams and molecular electrostatic potential maps. The anticancer properties of the compounds were evaluated in silico, comparing them to 5-fluorouracil (5-FU) against several cancer cell lines. The compounds exhibited the most effective anticancer activity against MCF-7 cells, with the order of anticancer activities generally determined as 2 > 7 > 3 > 6 > 5 > 4 > 5-FU.Öğe Bromokamfenlerin Etkin Sentezi, Suzuki Kenetlenme ve Yer Değiştirme ReaksiyonlarıiIle Yeni Türevlerin Sentezi(2020) Tutar, Ahmet; Ökten, Salih; Yılmaz, Raşit Fikret; Islam, Md ZahıdulBu projede doğal bir bileşik olan kamfenin yer değiştirme ve Suzuki-Miyaura kenetlenme reaksiyonları ile biyoaktif özelliğe sahip yeni türevlerinin sentezlenmesi amaçlanmıştır. Kamfen türevlerinin sentezi için farklı metotlar geliştirilmiştir. Fakat kamfenin brominasyonu sırasında düzenlenme ürünlerinin oluşması ve reaksiyon verimlerinin düşük olması yeni türevlerin sentezini sınırlamıştır. Grubumuzdaki çalışmalarla, farklı reaksiyon şartları uygulanarak düzenleme durdurulmuş ve yeni kamfen türevlerinin sentezi için yeni bir metodoloji geliştirmiştir. Kenetlenme reaksiyonları ve yer değiştirme reaksiyonları da sentetik kimyada önemli temel reaksiyonlardır. Bu projede, kamfenbromürlerin farklı sübstitüentlerle yer değiştirme reaksiyonları ve farklı boronik asitlerle kenetlenme reaksiyonları incelenmiştir. Bu çalışma ile doğal bileşik olan kamfenin kenetlenme reaksiyonu ilk kez yapılarak yeni potansiyel biyoaktif bileşikler sentezlenmiştir. Hedeflenen bileşiklerin sentezlenmesinde aşağıdaki reaksiyon basamakları uygulanmıştır. (1) (-)-Kamfen ve (+)-kamfenden çıkılarak monobromokamfenler sentezlendi. Bu sentez aşamasında (-)-kamfen, 650 W ışıkta moleküler brom ile muamele edilerek dibromokamfen hazırlandı. Ardından THF içerisinde t-BuOK ile muamele edilerek monobromokamfen karışımı elde edildi. Bu karışıma gerekli saflaştırma işlemleri uygulanarak E- ve Zbromokamfen türevleri elde edildi. (2) E-bromokamfenin, 5 farklı boronik asit ile Suzuki- Miyaura kenetleme reaksiyonları yapıldı. Bu sentezde E-bromokamfen, katalitik miktarda Pd(OAc)2 varlığında toluen içerisinde kaynatıldı. Gerekli saflaştırma işlemlerinden sonra hedeflenen aril sübstitüe kamfen bileşikleri elde edildi. (3) E-bromokamfenin, yer değiştirme reaksiyonları yapıldı. Bu sentezde E-bromokamfen, ayrı ayrı CH3Ona ve CuCN ile DMF içerisinde etkileştirilerek metoksi ve siyano kamfen türevleri elde edildi. (4) Elde edilen bileşiklerin spektroskopik ölçümleri ve yapı analizleri incelenmiştir. Kamfen halkasında düzenlenmenin durdurulabildiği, brominasyon ile fonksiyonel hale getirilerek yeni moleküllerin sentezlenebileceği gösterilmiştir.Öğe Determination of anticancer and antibacterial activities of disubstituted tacrine derivatives(2019) Ökten, Salih; Aydın, Ali; Tutar, AhmetThe present study describes the biological features of disubstituted tacrine derivatives using cell proliferation andcell cytotoxicity assays. The abilities of tacrine derivatives to inhibit microbial growth and to interact with DNA werealso investigated. Here, the tested compounds (1-4) exhibited selective antiproliferative activity against the cancercell lines (IC50 values 1.1 – 38.9 ?g/mL) and showed a similar non-toxic property to cells such as positive control(percent cytotoxicity 7% - 27%). Studies on human pathogenic bacteria showed that the novel tacrine analoguesexhibited significant antimicrobial activities between concentrations of 31.25 ?g/mL and 250 ?g/mL. The data showthat they can bind to DNA with the groove binding mode with Kb range of 7.4 10? - 2.9 10? M?¹. As a result, thepreliminary data showed that disubstituted tacrine derivatives exhibited effective pharmacological properties.Öğe In–Vitro Anticancer and Antibacterial Activities of Brominated Indeno[1,2-b]qinoline Amines Supported with Molecular Docking and MCDM**(John Wiley and Sons Inc, 2021) Aydın, Ali; Ökten, Salih; Erkan, Sultan; Bulut, Merve; Özcan, Evrencan; Tutar, Ahmet; Eren, TamerThe present study describes mono substituted indeno[1,2-b]quinolines (3 a–c and 5) have much more antiproliferative potentials than positive controls against A549, HeLa, MCF7 and Hep3B cell lines (IC50 values 1.1–29.6 ?g/mL) and show similar cytotoxicity (14.3 % to 19.8 %) to cells such as controls. Moreover, the mono substituted indeno[1,2-b]quinoline amines (3 a–c and 5) exhibit significant antimicrobial activity with MIC values between 15.62 ?g/mL and 250 ?g/mL. The compounds can also bind to DNA in the groove binding mode with a binding constant range of 1.1×103–1.1×105 M?1. The anticancer and antibacterial properties of compounds were confirmed with the molecular docking simulation for their pharmacokinetic. As a result, the preliminary experimental data and a multi-criteria decision-making methodology (MCDM) indicated that the mono substituted indeno[1,2-b]quinoline amine derivatives, especially 3 a and 5, exhibit effective pharmacological properties. parameters and their interaction with related cells at the molecular level. © 2021 Wiley-VCH GmbHÖğe N-function Heterocycles as Promising Anticancer Agents: A Case Study with a Decision Model in a Fuzzy Environment(Bentham Science Publ Ltd, 2024) Bulut, Merve; Ökten, Salih; Özcan, Evrencan; Eren, TamerObjective This study aimed to evaluate the data according to five accepted criteria for the effects of twenty promising anticancer agents on five different cancer types and determine the most effective compounds for further in vitro and in vivo studies with a multi-criteria decision-making method (MCDM), which rationalizes decision making in a fuzzy environment to avoid the high cost and time requirements of further preclinical and clinical studies.Methods Within the scope of the study, the weights of the five criteria were evaluated with the Pythagorean Fuzzy Analytic Hierarchy Process (PFAHP), which is one of the multi-criteria decision-making methods, and a comparison was made with the criteria weights obtained as a result of the Complex Proportional Assessment (COPRAS) method. Moreover, the effects of criteria weights calculated with PFAHP on evaluating alternatives were analyzed using different scenarios.Results Experimentally, twenty N-heterocyclic quinoline derivatives with different substituents were identified as promising anticancer agents. In this study, the multi-criteria decision-making (MCDM) model was proposed to identify the most promising anticancer agents against all tested cell lines. Both the experimental and model results indicated that 20, 17, 19, and 7 are the most promising anticancer agents against the A549, HeLa, Hep3B, HT29, and MCF7 cell lines. Moreover, different scenarios were generated and analyzed to prove the consistency of the proposed methodology.Conclusion MCDM strongly suggests that compounds 20, 17, 19, and 7 can be further investigated for in vivo studies.Öğe Novel diarylated tacrine derivatives: Synthesis, characterization, anticancer, antiepileptic, antibacterial, and antifungal activities(Wiley, 2024) Mısır, Büşra A.; Derin, Yavuz; Ökten, Salih; Aydın, Ali; Koçyiğit, Ümit M.; Şahin, Hatice; Tutar, AhmetIn this study, our goal was to synthesize novel aryl tacrine derivatives and assess their potential as anticancer, antibacterial agents, and enzyme inhibitors. We adopted a two-step approach, initiating with the synthesis of dibromotacrine derivatives 3 and 4 through the Friedlander reaction. These intermediates underwent further transformation into diarylated tacrine derivatives 3a-e and 4a-e using a Suzuki-Miyaura cross-coupling reaction. Thorough characterization of these novel diarylated tacrines was achieved using various spectroscopic techniques. Our findings highlighted the potent anticancer effects of these innovative compounds across a range of cancer cell lines, including lung, gynecologic, bone, colon, and breast cancers, while demonstrating low cytotoxicity against normal cells. Notably, these compounds surpassed the control drug, 5-Fluorouracil, in terms of antiproliferative activity in numerous cancer cell lines. Moreover, our investigation included an analysis of the inhibitory properties of these novel compounds against various microorganisms and cytosolic carbonic anhydrase enzymes. The results suggest their potential for further exploration as cancer-specific, enzyme inhibitory, and antibacterial therapeutic agents. Notably, four compounds, namely, 5,7-bis(4-(methylthio)phenyl)tacrine (3d), 5,7-bis(4-(trifluoromethoxy)phenyl)tacrine (3e), 2,4-bis(4-(trifluoromethoxy)phenyl)-7,8,9,10-tetrahydro-6H-cyclohepta[b]quinolin-11-amine (4e), and 6,8-dibromotacrine (3), emerged as the most promising candidates for preclinical studies. The novel aryl substituted tacrine were efficiently synthesized and their anticancer potentials were highlighted in this study. Their inducing apoptosis, cell migration, and mitochondrial membrane potentials were screened. imageÖğe Novel methoxyquinoline derivative: Synthesis, characterization, crystal structure, Hirshfeld surface, thermodynamic properties, and quantum chemical calculation of 3,6,8-trimethoxyquinoline(Taylor & Francis Ltd, 2021) Ökten, Salih; Demircioğlu, Zeynep; Erşanlı, Cem Cüneyt; Çakmak, OsmanIn this study, we describe the synthesis and structural characterization of novel 3,6,8-trimethoxyquinoline (2) by X-ray, FT-IR, NMR analysis, and its computational investigations. The molecular geometry of title coumpound was also optimized by using density functional theory (DFT/B3LYP) and Hartree-Fock (HF) methods with the 6-311 G(d,p) basis set, and geometric parameters were compared with the experimental data. Theoretical calculations are a good way for obtaining comprehensive information about global and local chemical activity, and chemical and molecular properties that reveal the nucleophilic and electrophilic nature. Molecular electrostatic potential (MEP) distribution, thermodynamic parameters, frontier molecular orbitals (FMOs), Fukui functions, and net charge analysis of (2) were also investigated. Also, the interactions between the molecule with DNA bases such as guanine, adenine, thymine, and cytosine were investigated by using the electrophilicity-based charge transfer (ECT) method and charge transfer (Delta N) for investigating the charge transfer, electrophilic, and nucleophilic nature.Öğe Production and characterization of fruit jam with activated pectin using wild hawthorn puree (Crataegus monogyna Jacq.)(Taylor & Francis Ltd, 2023) Farzaliev, Elsevar Babaoglu; Ökten, SalihIn this study, we developed a technology for the production of jelly confiture based on natural hawthorn puree. The use of activated low-esterified hawthorn pectin in the recipe was shown to increase the complexing ability of the product in relation to zinc and lead ions, making it suitable for functional preventive nutrition. The final product was characterised by a bright orange-yellow colour, a distinct hawthorn taste and odour, and a gelatinous consistency. Evaluation of the product based on organoleptic, physicochemical, and microbiological indicators showed that it had high nutritional and physiological value due to its retention of native micronutrients, high content of potassium, magnesium, and calcium, and antioxidant activity. The use of this product in a daily diet can satisfy the daily need for physiologically active substances and food ingredients. Overall, the use of natural puree from wild hawthorn fruit in the technology of jelly confiture allows for the expansion of raw material sources in the production of confectionery products with high nutritional and physiological value. [GRAPHICS]Öğe Production of organic light-emitting diode with fluorescence featured quinoline derivative(2021) Doğan, Mustafa; Erdem, Ümit; Ökten, SalihHigh-priced coating devices limit producing electronic devices and circuit applications widely in laboratories. Simply In this study spin coating technique was used to create surface thin films. Also with this method, an OLED(Organic Light Emitting Diode) device was practically produced. OLED device includes mainly HTL(hole transfer layer), fluorescent layer(light-emitting layer), and an ETL(electron transfer layer). Light-emitting layers in OLED experimental studies are frequently done with commercially produced expensive fluorescence polymers. As an example, MEH-PPV (Poly[2-methoxy-5-(2’-ethyl-hexoxy)-1,4-phenylenevinylene]), Alq3 (Tris-(8-hydroxyquinolinato) aluminum) are mostly known and used fluorescent semiconductor polymers. Alternative to these fluorescent polymers, three different produced quinoline ligand products has fluorescent feature were evaluated. After comparing the fluorescence yields of the produced three complexes, it was seen that 5,7-dibromo-8-hydroxyquinoline has the highest fluorescent response from the others. OLED device production was done with a commercial MEH-PPV(commercial) fluorescent product, and produced (5,7-dibromo-8-hydroxyquinoline). Designed OLED device illumination spectrum was found in the UV(ultraviolet) region. It was concluded that this quoniline product can use as a fluorescent material to produce an OLED device.Öğe Quinoline-based promising anticancer and antibacterial agents, and some metabolic enzyme inhibitors(WILEY-V C H VERLAG GMBH, 2020) Ökten, Salih; Aydın, Ali; Koçyiğit, Ümit M.; Çakmak, Osman; Erkan, Sultan; Andaç, Cenk A.; Taslimi, ParhamA series of substituted quinolines was screened for their antiproliferative, cytotoxic, antibacterial activities, DNA/protein binding affinity, and anticholinergic properties by using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide cell proliferation, lactate dehydrogenase cytotoxicity, and microdilution assays, the Wolfe-Shimmer equality method, the Ellman method, and the esterase assay, respectively. The results of the cytotoxic and anticancer activities of the compounds displayed that 6-bromotetrahydroquinoline (2), 6,8-dibromotetrahydroquinoline (3), 8-bromo-6-cyanoquinoline (10), 5-bromo-6,8-dimethoxyquinoline (12), the novelN-nitrated 6,8-dimethoxyquinoline (13), and 5,7-dibromo-8-hydroxyquinoline (17) showed a significant antiproliferative potency against the A549, HeLa, HT29, Hep3B, and MCF7 cancer cell lines (IC50 = 2-50 mu g/ml) and low cytotoxicity (similar to 7-35%) as the controls, 5-fluorouracil and cisplatin. The compound-DNA linkages are hyperchromic or hypochromic, causing variations in their spectra. This situation shows that they can be bound to DNA with the groove-binding mode, withK(b)value in the range of 2.0 x 10(3)-2.2 x 10(5) M-1. Studies on human Gram(+) and Gram(-) pathogenic bacteria showed that the substituted quinolines exhibited selective antimicrobial activities with MIC values of 62.50-250 mu g/ml. All tested quinoline derivatives were found to be effective inhibitors of acetylcholinesterase (AChE) and the human carbonic anhydrase I and II isoforms (hCA I and II), withK(i)values of 46.04-956.82 nM for hCA I, 54.95-976.93 nM for hCA II, and 5.51-155.22 nM for AChE. As a result, the preliminary data showed that substituted quinolines displayed effective pharmacological features. Molecular docking studies were performed to investigate the binding modes and interaction energies for compounds2-17with AChE (PDB ID: 4EY6), hCA I (PDB ID: 1BMZ), and hCA II (PDB ID: 2ABE).Öğe Regioselective bromination: Synthesis of brominated methoxyquinolines(Pergamon-Elsevier Science Ltd, 2017) Çakmak, Osman; Ökten, SalihSimple synthetic methods are described for the synthesis of valuable polyfunctional brominated methoxyquinolines 10-13, 20-21, and 24-25. Three regioselective routes are described for convenient preparation of brominated methoxyquinolines at the C-2, C-3, and C-5 positions with consecutive reaction steps under mild reaction conditions using molecular bromine. While bromination of 6-bromo-8methoxy-1,2,3,4-tetrahydroquinoline (8) selectively gave 3,6-dibromo-8-methoxyquinoline (10) and 3,5,6-tribromo-8-methoxyquinoline (11), the reaction of 6,8-dimethoxy-1,2,3,4-tetrahydroquinoline (9) resulted in the formation of 3-bromo-6,8-dimethoxyqinoline (12) and tribromide 13. On the other hand, direct bromination of 6-methoxy- 17 and 6,8-dimethoxyquinoline (19) gave 5-bromo derivatives 20 and 21. However, the reaction 3,6-dimethoxyquinoline (8) resulted in dibromination to form 2,5dibromoquinoline (24). This process selectively led to functionalization of the quinoline ring at both the C-2 and C-5 positions. (C)2017 Elsevier Ltd. All rights reserved.Öğe Structural Characterization of 6-Bromo-5-nitroquinoline-1-oxide: A Quantum Chemical Study and XRD Investigations(2018) Ökten, Salih; Ersanlı, Cem Cüneyt; Çakmak, OsmanThe chemical properties of recently synthesized 6-bromo-5-nitroquinoline-1-oxide under a mild reaction condition by regioselective nitration of 6-bromoquinoline-1-oxide at C5 on going our research were investigated as theoretical. The crystal structure of 6-bromo-5-nitroquinoline-1-oxide, C9H5BrN2O3, was determined by X-ray analysis. Crystallized in Pmc21 in the orthorhombic space group with a 13.6694 (13) Å, b 9.6036 (10) Å, c 14.1177 (16) Å, Z 8, Dx 1.929 mg/m3. In this study, theoretical calculations were performed using the GaussView 4.1 molecular imaging program and the Gaussian03W packet program. In the ground state, stable structures of the wholes molecule in the gaseous phase are investigated based on Density Functional Theory (DFT). Molecularly optimized geometries, dipole moments, charge density, thermodynamic properties (heat capacity, enthalpy, entropy), chemical shift values (1H NMR and 13C NMR), energies, molecular electrostatic potentials and frontier orbitals (HOMO and LUMO) B3LYP/6-311G(d,p) base set. Thus, the results obtained by the X-ray diffraction method are supported by theoretical foundations. Finally, the distribution of interactions between molecules in the crystal structure of 6-bromo-5-nitroquinoline-1-oxide (3) was investigated by analysis using Hirshfeld surface production and two-dimensional fingerprinting.Öğe Synthesis and spectral properties of symmetrically arylated BODIPY dyes: Experimental and computational approach(Elsevier, 2023) Yilmaz, Rasit Fikret; Derin, Yavuz; Mısır, Büşra Albayrak; Atalay, Vildan Enisoglu; Tutar, Ömer Faruk; Ökten, Salih; Tutar, AhmetIn this study, a series of symmetrically arylated BODIPY dyes were synthesized using a pre-functionalization method, and their structures were characterized by several spectroscopic methods. The relationship between the aryl substitution pattern and the photophysical and electrochemical properties of the dyes was investigated using experimental and computational methods. It was found that electron-donating & pi;-conjugated groups at the meso position and electron-accepting & pi;-conjugated groups at the C3/C5 position led to blue-shifted spectra, while the opposite substitution pattern resulted in red-shifted spectra. Additionally, inductive electron-donating alkyl groups at the meso position produced a blue spectral shift and an alkyl group at the meso position significantly increased the fluorescence quantum yield compared to the arylated counterparts. Computational investigations revealed that a thioanisyl group at the C3/C5 position resulted in a significantly narrow band gap. These results provide valuable insights into the design and development of new BODIPY dyes with tailored properties for various applications.Öğe Synthesis of aryl-substituted quinolines and tetrahydroquinolines through Suzuki-Miyaura coupling reactions(Sage Publications Ltd, 2019) Ökten, SalihThe synthesis and characterization of substituted (trifluoromethoxy, thiomethyl, and methoxy) phenyl quinolines is described. Dichlorobis(triphenylphosphine)palladiunn(II)-catalyzed Suzuki-Miyaura cross-coupling of 6-bromo- and 6,8-dibronno-1,2,3,4-tetrahydroquinolines, 5-bromo-8-methoxyquinoline, and 5,7-dibromo-8-methoxyquinoline with substituted phenylboronic acids affords the corresponding 6-aryl- (13a-d), 6,8-diaryl- (14a-c), 5-aryl- (15), and 5,7-diaryl- (16b, c) tetrahydroquinolines and quinolines in high yields (68%-82%). The structures of all the products are characterized by H-1 NMR, C-13 NMR, F-1(9) NMR, and Fourier transform infrared spectroscopy and by elemental analysis.
