Synthesis, characterization, preliminary SAR and molecular docking study of some novel substituted imidazo[2,1-b][1,3,4]thiadiazole derivatives as antifungal agents

Er, Mustafa; Ergüven, Buğracan; Tahtacı, Hakan; Onaran, Abdurrahman; Karakurt, Tuncay; Ece, Abdulilah

doi:10.1007/s00044-017-1782-4

Cited by 38 publications

(33 citation statements)

References 38 publications

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“…In conclusion, it is possible to say that ligands 5 , 6 , and 8 could be candidate inhibitor molecules for the 2RKV target structure. Also, as seen in Table and stated in the literature , high HOMO energy values resulted in high docking scores. The findings obtained in this study suggest that these compounds could be new potential inhibitors with biological activity for the 2RKV protein structure and used in in vitro studies.…”

Section: Resultssupporting

confidence: 58%

“…2‐Amino‐1,3,4‐thiadiazole derivatives ( 2a and 2b ) were obtained from reactions of nitrile compounds ( 1a and 1b ) with thiosemicarbazide in trifluoroacetic acid with high yields (82% and 79%, respectively). The nitrile derivatives ( 1a and 1b ) used as starting materials to synthesize imidazo[2,1‐ b ][1,3,4]thiadiazole derivatives ( 4 – 16 ) were commercially obtained, while 2‐amino‐1,3,4‐thiadiazole derivatives ( 2a and 2b ) were obtained as specified in the literature .…”

Section: Resultsmentioning

confidence: 99%

“…In the positive control, 50% Manep (2000 μg/mL), 80% Thiram (3000 μg/mL), and 80% Captan (2000 μg/mL) were used against the test fungi at the recommended doses. All antifungal activity values were determined by measuring the inhibition zone distance between the pathogen and paper disc .…”

Section: Methodsmentioning

confidence: 99%

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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

Tahtacı

Karakurt

et al. 2019

Journal of Heterocyclic Chem

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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 1H NMR, 13C 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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Section: Resultssupporting

confidence: 58%

Section: Resultsmentioning

confidence: 99%

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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

Tahtacı

Karakurt

et al. 2019

Journal of Heterocyclic Chem

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“…One of the main aim of the molecular docking is to map the ligand/target interactions to assist the rational drug design. The commonly used docking software available at the market are able to accurately and reliably predict the binding pose of the ligands in many cases, however, the scoring functions have a lower success rate in discriminating between active and inactive compounds ,,. Docking scores of the compounds 5 – 28 together with that of the reference compound, Chloramphenicol are given in Table .…”

Section: Resultsmentioning

confidence: 99%

“…Owing to the fact that imidazo[2,1‐ b ][1,3,4]thiadiazoles and their derivatives exhibit many biological activities such as antimicrobial,, antifungal, antibacterial, anti‐inflammatory, antituberculosis, analgesic, diuretic activities, the synthesis of these compounds and their derivatives increases gradually ,…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, SAR and Molecular Modeling Studies of Novel Imidazo[2,1‐b][1,3,4]Thiadiazole Derivatives as Highly Potent Antimicrobial Agents

Tahtacı

Karacık

Ece

et al. 2017

Molecular Informatics

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In this study, a novel series of phenyl substituted imidazo[2,1-b][1,3,4]thiadiazole derivatives were synthesized, characterized and explored for antibacterial activity against Gram-negative Escherichia coli, Gram-positive Staphylococcus aureus and Bacillus subtilis and antifungal activity against Candida albicans. Most of the synthesized compounds exhibited remarkable antimicrobial activities, some of which being ten times more potent than positive controls. The most promising compound showed excellent activity with MIC value of 0.03 μg/ml against both S. aureus and B. subtilis (MIC values of positive compound Chloramphenicol are 0.4 μg/ml and 0.85 μg/ml, respectively). Furthermore, structure-activity relationship was also investigated with the help of computational tools. Some physicochemical and ADME properties of the compounds were calculated too. The combination of electronic structure calculations performed at PM6 level and molecular docking simulations using Glide extra-precision mode showed that the hydrophobic nature of keto aryl ring with no electron withdrawing substituents at para position enhances activity while electron-donating substituents at the second aryl ring is detrimental to activity.

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The effects of morin and methotrexate on pentose phosphate pathway enzymes and GR/GST/TrxR enzyme activities: An in vivo and in silico study

Caglayan,

Temel,

Türkeş

et al. 2023

Archiv der Pharmazie

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In this study, the mechanisms by which the enzymes glucose‐6‐phosphate dehydrogenase (G6PD), 6‐phosphogluconate dehydrogenase (6PGD), glutathione reductase (GR), glutathione‐S‐transferase (GST), and thioredoxin reductase (TrxR) are inhibited by methotrexate (MTX) were investigated, as well as whether the antioxidant morin can mitigate or prevent these adverse effects in vivo and in silico. For 10 days, rats received oral doses of morin (50 and 100 mg/kg body weight). On the fifth day, a single intraperitoneal injection of MTX (20 mg/kg body weight) was administered to generate toxicity. Decreased activities of G6PD, 6PGD, GR, GST, and TrxR were associated with MTX‐related toxicity while morin treatment increased the activity of the enzymes. The docking analysis indicated that H‐bonds, pi–pi stacking, and pi–cation interactions were the dominant interactions in these enzyme‐binding pockets. Furthermore, the docked poses of morin and MTX against GST were subjected to molecular dynamic simulations for 200 ns, to assess the stability of both complexes and also to predict key amino acid residues in the binding pockets throughout the simulation. The results of this study suggest that morin may be a viable means of alleviating the enzyme activities of important regulatory enzymes against MTX‐induced toxicity.

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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

Cited by 38 publications

References 38 publications

Novel Substituted Imidazo[2,1‐b][1,3,4]Thiadiazole Derivatives: Synthesis, Characterization, Molecular Docking Study, and Investigation of Their In Vitro Antifungal Activities

Novel Substituted Imidazo[2,1‐b][1,3,4]Thiadiazole Derivatives: Synthesis, Characterization, Molecular Docking Study, and Investigation of Their In Vitro Antifungal Activities

Design, Synthesis, SAR and Molecular Modeling Studies of Novel Imidazo[2,1‐b][1,3,4]Thiadiazole Derivatives as Highly Potent Antimicrobial Agents

The effects of morin and methotrexate on pentose phosphate pathway enzymes and GR/GST/TrxR enzyme activities: An in vivo and in silico study

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