Yazar "Onaran, Abdurrahman" seçeneğine göre listele

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    An integrated approach towards the development of novel antifungal agents containing thiadiazole: synthesis and a combined similarity search, homology modelling, molecular dynamics and molecular docking study
    (Springeropen, 2018) Er, Mustafa; Abounakhla, Abdulati Miftah; Tahtaci, Hakan; Bawah, Ali Hasin; Cinaroglu, Suleyman Selim; Onaran, Abdurrahman; Ece, Abdulilah
    BackgroundThis study aims to synthesise and characterise novel compounds containing 2-amino-1,3,4-thiadiazole and their acyl derivatives and to investigate antifungal activities. Similarity search, molecular dynamics and molecular docking were also studied to find out a potential target and enlighten the inhibition mechanism.ResultsAs a first step, 2-amino-1,3,4-thiadiazole derivatives (compounds 3 and 4) were synthesised with high yields (81 and 84%). The target compounds (6a-n and 7a-n) were then synthesised with moderate to high yields (56-87%) by reacting 3 and 4 with various acyl chloride derivatives (5a-n). The synthesized compounds were characterized using the IR, H-1-NMR, C-13-NMR, Mass, X-ray (compound 7n) and elemental analysis techniques. Later, the in vitro antifungal activities of the synthesised compounds were determined. The inhibition zones exhibited by the compounds against the tested fungi, their minimum fungicidal activities, minimum inhibitory concentration and the lethal dose values (LD50) were determined. The compounds exhibited moderate to high levels of activity against all tested pathogens. Finally, in silico modelling was used to enlighten inhibition mechanism using ligand and structure-based methods. As an initial step, similarity search was carried out and the resulting proteins that belong to Homo sapiens were used as reference in sequence similarity search to find the corresponding amino acid sequences in target organisms. Homology modelling was used to construct the protein structure. The stabilised protein structure obtained from molecular dynamics simulation was used in molecular docking.ConclusionThe overall results presented here might be a good starting point for the identification of novel and more active compounds as antifungal agents.
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    Novel Substituted Imidazo[2,1-b][1,3,4]Thiadiazole Derivatives: Synthesis, Characterization, Molecular Docking Study, and Investigation of Their In Vitro Antifungal Activities
    (Wiley, 2019) Er, Mustafa; Tahtaci, Hakan; Karakurt, Tuncay; Onaran, Abdurrahman
    In this study, a new series of substituted imidazo[2,1-b][1,3,4]thiadiazole derivatives were synthesized. To this end, first 2-amino-1,3,4-thiadiazole derivatives (compounds 2a and 2b), the starting materials, were synthesized with high yields (82% and 79%, respectively). Then imidazo[2,1-b][1,3,4]thiadiazole derivatives (4-16), the target compounds, were synthesized from reactions of 2-amino-1,3,4-thiadiazole derivatives (2a and 2b) with 2-bromoacetophenone derivatives (3a-3i) (in yields of 52% to 71%). All of the synthesized compounds were characterized by H-1 NMR, C-13 NMR, Fourier transform infrared, elemental analysis, mass spectroscopy, and X-ray diffraction analysis (compounds 4-12, 14, and 15) techniques. In vitro antifungal activity tests were performed for all of the synthesized compounds. Inhibition zones, percentage of inhibition, minimum fungicidal activity, minimum inhibitory concentration, and lethal dose values of the target compounds were determined against some plant pathogens. According to the results of the biological activity tests, all of the synthesized compounds showed moderate to high levels of antifungal activity. Theoretical calculations were performed to support the experimental results. The geometric parameters of selected compounds (5, 6, and 8) were optimized using the density functional theory B3LYP/6-31G(d) method in the Gaussian 09W package program, and the frontier molecular orbitals (highest occupied molecular orbital-lowest unoccupied molecular orbital) were calculated theoretically. Finally, molecular docking studies were performed for antifungal activity studies of the selected compounds and to determine whether or not these compounds could be inhibitor agents for the 2RKV protein structure.
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    Synthesis, Characterization, Antimicrobial Evaluation, and Computational Investigation of Substituted Imidazo[2,1-b][1,3,4]Thiadiazole Derivatives
    (Wiley-V C H Verlag Gmbh, 2020) Dagli, Meltem; Er, Mustafa; Karakurt, Tuncay; Onaran, Abdurrahman; Alici, Hakan; Tahtaci, Hakan
    In this study, a novel series of 2,6-disubstituted and 2,5,6-trisubstituted imidazo[2,1-b][1,3,4]thiadiazole derivatives were synthesized starting from 2-amino-1,3,4-thiadiazole derivatives. Structures of the synthesized compounds were characterized using various analysis techniques. Then, in vitro biological activity tests were carried out for all synthesized compounds and they were found to show moderate to good activity against all bacteria and fungi tested. Next, molecular docking simulations were performed to observe the inhibition effect of the synthesized compounds on the 3R9C receptor and support their biological activity results. Finally, the pharmacokinetic, ADME and toxicity properties of all compounds were examined using FAF-Drugs and ProTox webservers and it was concluded that they had acceptable toxicity and ADME properties.
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    Synthesis, characterization, preliminary SAR and molecular docking study of some novel substituted imidazo[2,1-b][1,3,4]thiadiazole derivatives as antifungal agents
    (Springer Birkhauser, 2017) Er, Mustafa; Erguven, Bugracan; Tahtaci, Hakan; Onaran, Abdurrahman; Karakurt, Tuncay; Ece, Abdulilah
    The aim of this study was to synthesize imidazo[2,1-b][1,3,4]thiadiazole derivatives, characterize them with various spectroscopic methods and investigate their antifungal activities. 2-Imino-1,3,4-thiadiazole derivatives 2a, b were synthesized by reacting nitrile compounds 1a, b with thiosemicarbazide (yields 75 and 88%). We then synthesized imidazo[2,1-b][1,3,4]thiadiazole derivatives 4-21, the target compounds, from the reactions of 2-amino-1,3,4-thiadiazole derivatives 2a, b with phenacyl bromide derivatives 3 (yields 52-69%). The structures of all synthesized compounds were characterized by infrared, H-1 nuclear magnetic resonance, C-13 nuclear magnetic resonance, elemental analysis and mass spectroscopy and X-ray diffraction analysis was also used for the compounds 7, 8, 10, and 17. Subsequently, in vitro antifungal activity tests were applied to all synthesized compounds. Inhibition zones, percentages of inhibition and LD50 doses were determined. Most of the synthesized compounds exhibited good antifungal activity against plant pathogens. Molecular docking and electronic properties calculations were carried out in order to see the potential binding conformations of the ligands and the effect of the substituents on the activities. Docking score successfully reflects the activity of the most active compound 10, which was found to have the lowest octanol/water partition coefficient and high HOMO energy value. The combination of experimental and computational work show that all the synthesized compounds have promising activities and might serve as novel drug candidates.
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    Synthesis, Structural Characterization, and Biological Evaluation of Novel Substituted 1,3-Thiazole Derivatives Containing Schiff Bases
    (Wiley, 2017) Tahtaci, Hakan; Er, Mustafa; Karakurt, Tuncay; Onaran, Abdurrahman
    In this study, thiazole derivatives containing Schiff bases (7-9 a-f) were synthesized in moderate to high yields (49-94%) using the Hantzsch reaction with thiosemicarbazone derivatives (5a-c) and 2bromo- 1-phenylethanone derivatives (6a-f). The structures of synthesized compounds were elucidated by IR, H-1 NMR, C-13 NMR, elemental analyses, mass spectroscopy and X-ray diffraction analysis techniques. Moreover, the synthesized compounds were tested for their in vitro antifungal activity and most of them exhibited moderate to good activity against Fusariumoxysporumf.sp. lycopersici.
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    Synthesis, structural characterization, biological activity, and theoretical studies of some novel thioether-bridged 2,6-disubstituted imidazothiadiazole analogues
    (Wiley, 2021) Tunel, Hasan; Er, Mustafa; Alici, Hakan; Onaran, Abdurrahman; Karakurt, Tuncay; Tahtaci, Hakan
    In this study, thioether-bridged imidazo[2,1-b][1,3,4]thiadiazole derivatives that contained both imidazole and 1,3,4-thiadiazole (compounds 7a-7i and 8a-8i) were synthesized from the reactions of 2-amino-1,3,4-thiadiazole with phenacyl bromide (6a-6i) (at yields of 59% to 74%). The structure of the synthesized compounds was characterized using H-1 NMR, C-13 NMR, Fourier-transform infrared spectroscopy, elemental analysis, mass spectroscopy, and X-ray diffraction analysis. Mycelial growth, mycelial growth inhibition, minimum inhibitory concentration, minimum fungicidal concentration, and lethal dose values against various plant pathogenic fungi were determined for all of the target compounds synthesized in the study. The test results showed that most of the compounds had moderate to good antifungal activity. In addition, the absorption, distribution, metabolism, excretion (ADME) parameters of the compounds were calculated, and it was observed that all of the compounds met the drug-likeness rules in general. Finally, using docking simulations, it was found that compounds 7h, 7i, 8h, and 8i showed high affinity to PDB ID:5TZ1, which is an CYP51 antifungal target structure.