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    Inhibitory effects of sulfenimides on human and bovine carbonic anhydrase enzymes
    (Taylor & Francis Ltd, 2023) Yakan, Hasan; Bilir, Gurkan; Cakmak, Sukriye; Tas, Omer; Karakullukcu, Nalan Turkoz; Soydan, Ercan; Kutuk, Halil
    A series of sulfenimide derivatives (1a-i) were investigated as inhibitors of human (hCA-I, hCA-II) and bovine (bCA) carbonic anhydrase enzymes. The compounds were synthesised by the reaction of substituted thiophenols with phthalimide by means of an effective, simple and eco-friendly method and the structures were confirmed by IR, H-1 NMR, C-13 NMR, MS and elemental analysis. All derivatives except for the methyl derivative (1b) exhibited effective inhibitory action at low micromolar concentrations on human isoforms, but only four derivatives (1e, 1f, 1h, 1i) inhibited the bovine enzyme. The bromo derivative (1f) was found to be strongest inhibitor of all three enzymes with KI values of 0.023, 0.044 and 20.57 mu M for hCA-I, hCA-II and bCA, respectively. Results of our study will make valuable contributions to carbonic anhydrase inhibition studies for further investigations since inhibitors of this enzyme are important molecules for medicinal chemistry.
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    New 5-methylisatin including thiocarbohydrazones: preparation, structure elucidation and antimicrobial activity
    (Springer, 2022) Yakan, Hasan; Cakmak, Sukriye; Buruk, Osman; Veyisoglu, Aysel; Muglu, Halit; Karakullukcu, Nalan Turkoz
    New 5-methylisatin including thiocarbohydrazones (1-5) have been synthesized. The chemical structure of synthesized compounds was elucidated with IR, H-1 NMR, C-13 NMR spectroscopic methods, and elemental analysis. Moreover, the synthesized compounds have been screened for antimicrobial activity. Their antibacterial activities were tested against Gram-positive (Bacillus subtilis ATCC 6623, Staphylococcus aureus ATCC 25923, Enterococcus faecalis ATCC 29212), Gram-negative (Escherichia coli ATCC 25922, Klebsiella pneumoniae ATCC 70060, Pseudomonas aeruginosa ATCC 27853), and fungal (Candida albicans ATCC 10231, Aspergillus niger ATCC 16404) microbial strains using the microdilution method. In the isatin series, particularly the compound 2 showed the best antimicrobial activity against E. faecalis strain with MIC values of 64 mu g/mL compared to other compounds. This high activity of compound 2 is due to the presence of two electron-donating methoxy groups in its structure. The remaining substituted compounds have shown good and moderate antimicrobial activity compared to standard drugs. The results may provide insights into the target compounds' structure-activity relationships, which may facilitate the development of pharmacological and biological applications for the target compounds. Graphical abstract New isatins bearing thiocarbohydrazone were synthesized. Structures of all com- pounds were elucidated with spectroscopic approaches. The antimicrobial activities of the tested compounds presented promising antimicrobial activity against the eight tested microorganisms.
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    Synthesis of some symmetric disulfides from thiophthalimides and amines under microwave irradiation
    (World Research Association, 2018) Yakan, Hasan; Karakullukcu, Nalan Turkoz; Cakmak, Sukriye; Kutuk, Halil
    Some symmetric disulfides have been astonishingly prepared from thiophthalimides (sulfenimides) and amines in the presence of 2-ethoxyethanol (β-ee, neat) at microwave irradiation under free catalyst and ligand. The products were obtained in good to excellent yields ranging from 62% to 92%. When only thiophthalimides were exposed to microwave irradiation, disulfides were not obtained. Also, disulfides were not obtained from thiophthalimides in the presence of 2-ethoxyethanol (neat) under microwave irradiation. We compared the microwave-assisted synthesis method with the classical method. The products obtained were purified with chromatographic method and the analysis of them was performed with IR, 1H NMR, 13C NMR spectroscopic and elemental methods. © 2018 World Research Association. All rights reserved.