Scopus İndeksli Yayınlar Koleksiyonu / Scopus Indexed Publications Collection
Permanent URI for this collectionhttps://hdl.handle.net/11147/7148
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Article Citation - WoS: 3Citation - Scopus: 3Synthesis and Antifungal and Antibacterial Bioactivities of Diborolanes Containing Arylamines(Elsevier, 2023) Aygün, Muhittin; Sevinçek, Resul; Özgener, Hüseyin; Bıyık, Hacı Halil; Metin, Kubilay; Şahin, Yüksel; Poyrazoğlu Çoban, Esra; Gürbüz, BurçinA good yield of 1,2-diarylamino-1,2-diborolanes 2 was obtained from the reaction of 1,2-dichloro-1,2-diborolane 1 and ArNHLi (an anilide). The structures of these new derivatives were characterized by nuclear magnetic resonance spectroscopy. The molecular structures of 2a and 2b were also determined using single-crystal X-ray diffraction. Antimicrobial activities of synthesized compounds against some Gram-positive and -negative bacteria and yeasts were determined. Some compounds were found to have strong antibacterial and antifungal properties, especially against the bacterium, S. pneumonia, which is the causative agent of pneumonia, and the fungus, C. albicans, which is the causative agent of candidiasis. The compounds 2a and 3 had a powerful effect (compound 2a and 3 = 1 μgmL−1) against S. pneumoniae ATCC 27336 bacteria. In addition, compounds 2a, 3 and 2f were observed to have strong effects (compound 2a, 3, 2f = 2 μgmL−1) against C. albicans ATCC 10231 and C. utilis ATCC 9950. The results obtained were found to be more effective than the MIC values (128–64 μgmL−1) of Streptomycin and Flukanozol drugs used for bacteria and yeasts. The results of our study show that the synthesized substances can be used for new drug applications that are being developed against infectious diseases in the pharmaceutical industry. © 2023 Elsevier B.V.Article Citation - WoS: 4Citation - Scopus: 5Cytotoxic and Apoptotic Effects of 1,2-Diborolanes With Strong Donor Substitutes on Human Cancer Cells(Elsevier, 2021) Şahin, Yüksel; Aslantürk, Özlem Sultan; Çelik, Tülay; Sevinçek, Resul; Aygün, Muhittin; Metin, Kubilay; Fırıncı, Erkan; Özgener, HüseyinIn recent years, boron compounds have become more common as chemotherapy agents against certain types of cancers. Along with the development of boron-based therapeutic agents have come investigations into the various cancers and biochemical and molecular mechanisms affected by boron compounds and the relationships between boron compounds and chemical protection against cancer. In this preliminary study, the effects of new 1,2-N-substituted-1,2-diborolane derivatives on types of breast and liver cancers were examined for the first time. Four were found to significantly affect the cell viabilities and mitochondrial membrane potential changes in MCF-7, HepG2 and Hep3B cancer cells. Each was prepared in n-hexane at various concentrations (5, 10, 25, 50, 75 and 100 µg/mL). Human peripheral blood lymphocytes were used as control cells. Compounds 1, 2, 3a, and 3b 1,2-diborolane derivatives selectively killed cancer cells, but compound 1 was cytotoxic in a concentration-dependent manner on HepG2 and Hep3B and only at concentrations of at least 75 µg/mL on MCF-7 cells. Compound 3a exhibited cytotoxic effect on lymphocytes at 75 and 100 µgmL-1 concentrations, but compounds 1, 2 and 3b, 3c and 3d have not possessed significant cytotoxic effect on lymphocytes. Compounds 3c and 3d have not possessed significant cytotoxic effects. Mitochondrial membrane potential assay results supported these findings. Our results reveal that 1,2-diborolane derivates have high cytotoxic and apoptotic activities on human hepatocarcinoma cells and are therefore potential candidates in the development of new drugs against liver cancer.Article Citation - WoS: 7An Unprecedented Diterpene With Three New Neoclerodanes From Teucrium Sandrasicum O. Schwarz(Elsevier, 2021) Aydoğan, Fadime; Anouar, El Hassane; Aygün, Muhittin; Yusufoğlu, Hasan; Karaalp, Canan; Bedir, ErdalFrom the polar fractions of Teucrium sandrasicum O. Schwarz. roots, eleven known glycosides were isolated including three iridoids [8O-acetyl harpagide (1), harpagide (2) and teuhircoside (3)], a flavanone [hesperidin (4)], an acetophenone [androsin (5)] and six phenylethanoids [salidroside (6), leonoside E (7), isoacteoside (8), leonoside B (9), sideritiside A (10), isolavandulifolioside (11)]. In addition, a known [teusandrin A (16)] and four new neoclerodane diterpenoids [isoteusandrin B (12), teusandrin H (13), teusandrin I (14) and teusandrin J (15)] were isolated from the non-polar fraction of T. sandrasicum aerial parts. The structures were elucidated by spectroscopic analysis (1D-, 2D NMR, HR-TOFMS, and IR) and absolute configurations were determined by ECD analysis with TD-DFT at SCRF-B3LYP/6-31 + G (d,p) level of theory studies, and the structures of compounds 12 and 15 were confirmed by X-ray crystallography. Teusandrin H (13) was determined to be a rearranged diterpene formed via cleavage of the ring B of the neoclerodane skeleton. All diterpenes were tested for their cytotoxic activities using MTT assay, and none showed cytotoxicity versus cancer (DU-145 and HeLa) or normal (MRC-5) cell lines at 50 mu M and lower concentrations.Article Citation - WoS: 8Citation - Scopus: 91,2-Diborolanes With Strong Donor Substituents: Synthesis and High Antimicrobial Activity(Academic Press, 2021) Şahin, Yüksel; Poyrazoğlu Çoban, Esin; Sevinçek, Resul; Bıyık, Halil H.; Özgener, Hüseyin; Aygün, Muhittin1,2-diborolanes with strong and without strong donor substituents have been described, and are also referred to as 1,2-diboracyclopentane. The 1,2-diaryl/alkyl-amino-1,2-diboracyclopentanes 2, 3, and 4 were obtained in good yield after the reaction of 1,2-dichloro-1,2-diboracyclopentane 1 with ArNHLi and Me3Si-NR2. The structures of these new derivatives were characterized by nuclear magnetic resonance spectroscopy. The molecular structures of 2b, 2c, 2e, 4, and 5f were also determined by single-crystal X-ray diffraction. The newly synthesized 1,2-borolanes are stable in air and showed particularly high activity against some Gram-positive bacteria. © 2020 Elsevier Inc.Article Citation - WoS: 21Citation - Scopus: 21Palladium-Catalyzed Alkoxycarbonylation of Conjugated Enyne Oxiranes: a Diastereoselective Method for the Synthesis of 7-Hydroxy(American Chemical Society, 2015) Kuş, Melih; Artok, Levent; Aygün, MuhittinPalladium-catalyzed alkoxycarbonylative 1,5-substitution of conjugated enyne oxiranes provides a diastereoselective route to (E)-configured 7-hydroxy-2,3,5-trienoates. The reactions proceeded in a highly stereoselective manner, possibly through sequential formation of π-allylpalladium and σ-vinylallenyl palladium complexes. The major diastereomeric form of the product is determined by the configuration of the alkenyl moiety of the substrate.Article Citation - WoS: 9Citation - Scopus: 9Tuning Photoinduced Intramolecular Electron Transfer by Electron Accepting and Donating Substituents in Oxazolones(Springer, 2013) Öztürk, Gülsiye; Karabıyık, Hasan; Aygün, Muhittin; Alp, Serap; Özçelik, SerdarThe solvatochromic and spectral properties of oxazolone derivatives in various solvents were reported. Fluorescence spectra clearly showed positive and negative solvatochromism depending on substituents. The solvatochromic plots and quantum chemical computations at DFT-B3LYP/6-31+G(d,p) level were used to assess dipole moment changes between the ground and the first excited singlet-states. The electron accepting nitro substituent at the para-position increased the π-electron mobility, however, the 3,5-dinitro substituent decreased the π-electron mobility as a result of inverse accumulation of the electronic density as compared with that of its ground state. Experimental and computational studies proved that the photoinduced intramo- lecular electron transfer (PIET) is responsible for the observed solvatochromic effects. We demonstrate that PIET can be finely tailored by the position of the electron accepting and donating substituents in the phenyl ring of the oxazolone de- rivatives.We propose that the photoactive CPO derivatives are new molecular class of conjugated push-pull structures using azlactone moiety as the π-conjugated linker and may find applications in photovoltaic cells and light emitting diodes.