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    Spectroscopic and structural aspects of the reactions of 1,4-quinones with sulfur and nitrogen nucleophiles
    (Elsevier France-Editions Scientifiques Medicales Elsevier, 2014) Bayrak, Nilufer; Tuyun, Amac Fatih; Yildirim, Hatice; Onul, Nihal
    A series of 1,4-benzoquinone derivatives from 2,5-dichloro-3,6-diethoxy-1,4-benzoquinone and 2,6-dichloro-3,5-diethoxy-1,4-benzoquinone were prepared by nucleophilic substitution reactions of sulfur and nitrogen nucleophiles. Spectral techniques (H-1 NMR, C-13 NMR, FT-IR, and LC-MS) were employed to structurally characterize the reaction products of alkoxy, chloro substituted-1,4-benzoquinones with thiols and amines in the presence of sodium carbonate in ethanol at room temperature. The orientations and the regioselectivity of the reactions of alkoxy, chloro substituted-1,4-benzoquinones with various thiol and amine nucleophiles are discussed. (C) 2013 Academie des sciences. Published by Elsevier Masson SAS. All rights reserved.
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    Synthesis and In Vitro Biological Evaluation of Aminonaphthoquinones and Benzo[b]phenazine-6,11-dione Derivatives as Potential Antibacterial and Antifungal Compounds
    (Hindawi, 2015) Tuyun, Amaç Fatih; Bayrak, Nilüfer; Yıldırım, Hatice; Onul, Nihal; Mataracı Kara, Emel; Özbek Çelik, Berna
    A series of 2-arylamino-3-chloro-1,4-naphthoquinone derivatives (3a–h) by the reaction of 2,3-dichloro-1,4-naphthoquinone with aryl amines (2a–h) and benzo[b]phenazine-6,11-dione derivatives (4a–c) by the treatment of 2-arylamino-3-chloro-1,4-naphthoquinone derivatives (3a–h) with sodium azide were synthesized and tested for their in vitro antibacterial and antifungal activities. The results suggest that compounds 3d and 3g had potent antifungal activity against Candida albicans (MIC = 78.12??g/mL). All synthesized compounds (3a–h, 4a–c) possessed activity against E. faecalis with MIC values of between 312.5 and 1250??g/mL. Benzo[b]phenazine-6,11-dione derivatives (4a–c) were mostly active against Gram-positive bacteria. The structures of the new members of the series were established on the basis of their spectral properties (IR, 1H NMR, 13C NMR, and mass spectrometry).