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Benzotiyazol ve 1,3,4-tiyadiazol içeren tek kristalin sentezi ve teorik olarak incelenmesi
(2019) Karakurt, Tuncay; Tahtacı, Hakan; Er, Mustafa
Bu çalışmada tiyadiazol ve benzotiyazol halkası içeren 3-((5-amino-1,3,4-tiyadiazol-2- il)metil)benzo[d]tiyazol-2(3H)-on bileşiğinin yapısı, X-ışını kırınım yöntemi ve IR, NMR spektroskopik yöntemler kullanılarak aydınlatılmıştır. Deneysel çalışmalara destek olması amacı ile de B3LYP metodu ve 6-31G(d,p) temel seti kullanılarak teorik çalışmalar yapılarak bazı yapısal parametreler hesaplanmıştır. Özellikle kristalin reaktif bölgelerini incelemek için kısmi atom yükü ve moleküler elektrostatik potansiyel (MEP) ve Hirshfeld yüzey analizleri yapıldı. Son olarak da AIM yük analizi kullanılarak moleküller arası etkileşimlerin özellikleri incelenmiştir. Hesaplanan sonuçların, X-ışını verileriyle uyumlu olduğu görülmüştür.
Novel 2-amino-1,3,4-thiadiazoles and their acyl derivatives: Synthesis, structural characterization, molecular docking studies and comparison of experimental and computational results
(Elsevier Science Bv, 2016) Er, Mustafa; Isildak, Gamze; Tahtaci, Hakan; Karakurt, Tuncay
This study aims to synthesize and characterize compounds containing 2-amino-1,3,4-thiadiazole and compare experimental results to theoretical results. For this purpose, firstly mono, di and tetra 2-amino-1,3,4-thiadiazole compounds (2a-c, 14, 20 and 25) were synthesized in relatively high yields (74-87%). The target compounds (3-11, 15-17, 21-23 and 26-28) were then synthesized in moderate to high yields (65-85%) from the reactions of 2-amino-1,3,4-thiadiazole compounds with various acyl chloride derivatives. The structures of all synthesized compounds were elucidated by IR, H-1 NMR, C-13 NMR, elemental analyses and mass spectroscopy techniques. The structures of 2b (C9H8N4O2S) and 2c (C11H13N3O2S) were also elucidated by X-ray diffraction analysis. Lastly, IR spectrum, H-1 NMR and C-13 NMR chemical shift values, frontier molecular orbital (FMO) values of these molecules containing heteroatoms were examined using the Becke-3- Lee-Yang-Parr (B3LYP) method with the 6-31G(d) basis set. Two different molecular structures containing 2-amino-1,3,4-thiadiazole (2b, 2c) were used in our study to examine these properties. Also, compounds 2b and 2c form a stable complex with beta-Lactamase as can be understood from the binding affinity values and the results show that the compound might inhibit the beta-Lactamase enzyme. It was found that theoretical and experimental results obtained in the experiment were compatible with each other and with the values found in the literature. (C) 2016 Elsevier B.V. All rights reserved.
Novel aldehyde and thiosemicarbazone derivatives: Synthesis, spectroscopic characterization, structural studies and molecular docking studies
(Elsevier, 2016) Karakurt, Tuncay; Tahtaci, Hakan; Subasi, Nuriye Tuna; Er, Mustafa; Agar, Erbil
In this study our purpose is that, synthesis and characterization of compounds containing the aldehyde and thiosemicarbazone groups and comparison of the theoretical results with the experimental results. The structures of all synthesized compounds were elucidated by IR, H-1 NMR, C-13 NMR, elemental analyses techniques. The structure of compound (4) (C9H8N4O2S) was also elucidated by X-ray diffraction analysis. In addition, the theoretical IR spectrum, H-1 NMR and C-13 NMR chemical shift values, frontier molecular orbital values (FMO) of these molecules were analyzed by using Becke-3- Lee-Yang-Parr (B3LYP) method with LanL2DZ basis set. Finally, molecular docking studies were performed on synthesized compounds using the 4DKI beta-lactam protein structure to determine the potential binding mode of inhibitors. (C) 2016 Elsevier B.V. All rights reserved.
A Novel Class Substituted Imidazo[2,1-b][1,3,4]thiadiazole Derivatives: Synthesis, Characterization, In Vitro Biological Activity, and Potential Inhibitors Design Studies
(Wiley-V C H Verlag Gmbh, 2019) Er, Mustafa; Ahmadov, Farid; Karakurt, Tuncay; Direkel, Sahin; Tahtaci, Hakan
In this study, imidazo[2,1-b][1,3,4]thiadiazole derivatives were designed and synthesized. All of the synthesized compounds were characterized by H-1 and C-13 nuclear magnetic resonance (H-1 NMR and C-13 NMR), fourier-transform infrared spectroscopy (FT-IR), elemental analysis, mass spectrometry, and X-ray diffraction. The synthesized compounds were tested for antileishmanial activity against two Leishmania species and antibacterial activity against nine bacterial species in the study. It was observed that 2-(4-Fluorobenzylthio)-6-(4-fluorophenyl)imidazo[2,1-b][1,3,4]thiadiazole (5) had the highest antileishmanial activity (MIC: 625 mu g/mL). Also, 4-(2-(4-fluorobenzylthio)imidazo[2,1-b][1,3,4]thiadiazol-6-yl)benzonitrile (10), 2-(4-fluorobenzylthio)-6-(4-phenylphenyl)imidazo[2,1-b][1,3,4]thiadiazole (11), and 4-(2-(4-methoxybenzyl)imidazo[2,1-b][1,3,4]thiadiazol-6-yl)benzonitrile (25) were found to be effective at different studied concentrations. PyRx software, which uses a Lamarckian genetics algorithm, was utilized to find the affinity values of all compounds in molecular docking simulations. Pharmacokinetic properties and toxicities of the ligands were then researched using PROTOX (a webserver for the prediction of oral toxicities of small molecules) and FAF-Drugs (free adsorption distribution, metabolism, excretion (ADME) tox filtering tool). The study showed that the ligands had acceptable toxicity and ADME properties for the inhibition of the 3JUS receptor.
Novel substituted benzothiazole and Imidazo[2,1b][1,3,4]Thiadiazole derivatives: Synthesis, characterization, molecular docking study, and investigation of their in vitro antileishmanial and antibacterial activities
(Elsevier, 2019) Er, Mustafa; Ozer, Arif; Direkel, Sahin; Karakurt, Tuncay; Tahtaci, Hakan
In this study, we synthesized new imidazo[2,1-b][1,3,4]thiadiazole derivatives containing benzothiazole group. To this end, we firstly obtained the benzo[d]thiazol-2-ylthio/oxy acetonitrile compounds (3a,b), the starting materials, in high yields (82% and 87%, respectively). Then, we synthesized the 2-amino-1,3,4-thiadiazole derivatives (4a,b) from the reaction of these nitrile derivatives (3a,b) with thio-semicarbazide in trifluoroacetic acid (TFA) (in yields of 83% and 84%). Finally, we synthesized the imidazo [2,1-b][1,3,4]thiadiazole derivatives (5-24) containing benzothiazole group, which are the target compounds, from reactions of 2-amino-1,3,4-thiadiazole derivatives (4a,b) with phenacyl bromide derivatives (in yields of 53%-73%). All of the compounds synthesized were characterized with H-1 NMR, C-13 NMR, FT-IR, elemental analysis, and mass spectroscopy. Antileishmanial and antibacterial activity tests were applied to the compounds synthesized in the study. It was observed that compound 8 had the highest antileishmanial activity (MIC = 10 000 mu g/mL). Also, compounds 7 and 17 were found to be effective at the highest concentration studied (MIC = 20 000 mu g/mL). In terms of antibacterial activity, compounds 4b and 7 were found to be the most effective compounds against Escherichia coli (MIC = 625 mu g/mL). Theoretical calculations were performed to support the experimental results. To this end, we performed Molecular Docking studies to determine whether or not the compounds (4a, 4b, 7 and 13) optimized with Gaussian09 using the DET/B3LYP/6-31G(d,p) theory, which is a quantum chemical calculation, could be an inhibitor agent for the 2eg7 Escherichia coli protein structure. Also, we investigated the relationship between the calculated HOMO values of these four ligands and docking studies. (C) 2019 Elsevier B.V. All rights reserved.
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.
Synthesis of 1,3,4-thiadiazol-2(3H)-one derivatives via an unexpected intramolecular addition-elimination reaction of 1,3,4-thiadiazoles
(Pergamon-Elsevier Science Ltd, 2017) Tahtaci, Hakan; Er, Mustafa; Karakurt, Tuncay; Sancak, Kemal
A new synthesis was developed for 1,3,4-thiadiazol-2(3H)-one derivatives, based on a new arrangement on the thiadiazole ring with an intramolecular addition-elimination reaction. To this end, starting from 5-methyl-1,3,4-thiadiazole-2-thiol (1), derivatives of 3-((un)substituted benzyl)-5-methyl-1,3,4-thiadiazol-2(3H)-one (7a-g) and ((un)substituted phenyl)-2-oxoethyl)-5-methyl,3,4-thiadiazol-2(3H)-one (10-15) were synthesized (in yields of 81-88% and 63-71%, respectively). The structures of all synthesized compounds were characterized using IR, H-1 NMR, and C-13 NMR spectroscopy, and elemental analysis, mass spectroscopy and X-ray diffraction analysis (compounds 3c, 7b-f and 10) techniques. This study presents a new and effective reaction path for the synthesis of 1,3,4-thiadiazol-2(3H)-one derivatives. (C) 2017 Elsevier Ltd. All rights reserved.
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.
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.
Synthesis, molecular docking, and preliminary cytotoxicity study of some novel 2-(naphthalen-1-yl)-methylimidazo[2,1-b][1,3,4] thiadiazoles
(Elsevier, 2021) Choodamani, B.; Kumar, Sujeet; Gupta, Alok Kumar; Schols, Dominique; Tahtaci, Hakan; Karakurt, Tuncay; Kotha, Satvik
A series of 2-(naphthalen-1-yl)-methyl-6-arylimidazo[2,1-b][1,3,4]thiadiazole derivatives was prepared and studied for cytotoxicity against murine leukemia L1210, human cervix carcinoma HeLa, and human T lymphocyte CEM cell lines. The preliminary study showed that compounds 5g, 6g, 7a-c, 7e, and 8e were more potent among the tested compounds. The pharmacokinetic properties of all compounds were then investigated with FAF-Drugs, a tool for prediction of ADME and toxicity. Finally, in order to support in vitro studies, molecular docking studies were performed by using AutoDock Vina with a Lamarckian genetic algorithm to determine whether or not the synthesized compounds could be used as inhibitors for the protein structure 1m17 (EGFR). The docking scores of many compounds were found to be higher than [6,7-bis(2-methoxy-ethoxy)quinazoline-4-yl]-(3-ethynyl phenyl)amine, an inhibitor of the 1m17 EGFR receptor. Among the selected compounds 7b, 7c, 7e, 7f, 7g, and 8g showed better stability in the molecular dynamics simulation study. (C) 2021 Elsevier B.V. All rights reserved.
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.
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.

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