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

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dc.authoridTAHTACI, HAKAN/0000-0002-1557-6315
dc.authoridkarakurt, tuncay/0000-0001-6944-9883
dc.contributor.authorEr, Mustafa
dc.contributor.authorTahtaci, Hakan
dc.contributor.authorKarakurt, Tuncay
dc.contributor.authorOnaran, Abdurrahman
dc.date.accessioned2024-09-29T15:50:44Z
dc.date.available2024-09-29T15:50:44Z
dc.date.issued2019
dc.departmentKarabük Üniversitesien_US
dc.description.abstractIn 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.en_US
dc.description.sponsorshipAhi Evran University [MMF.A4.18.011]en_US
dc.description.sponsorshipThe financial support by the Ahi Evran University (project ID number: MMF.A4.18.011) is gratefully acknowledged.en_US
dc.identifier.doi10.1002/jhet.3653
dc.identifier.endpage2570en_US
dc.identifier.issn0022-152X
dc.identifier.issn1943-5193
dc.identifier.issue9en_US
dc.identifier.scopus2-s2.0-85070772409en_US
dc.identifier.scopusqualityQ3en_US
dc.identifier.startpage2555en_US
dc.identifier.urihttps://doi.org/10.1002/jhet.3653
dc.identifier.urihttps://hdl.handle.net/20.500.14619/3706
dc.identifier.volume56en_US
dc.identifier.wosWOS:000481214000001en_US
dc.identifier.wosqualityQ3en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherWileyen_US
dc.relation.ispartofJournal of Heterocyclic Chemistryen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectGrowth-Factor-Betaen_US
dc.subjectBiological Evaluationen_US
dc.subjectDesignen_US
dc.subject1,3,4-Thiadiazoleen_US
dc.subjectAntibacterialen_US
dc.subjectKinasesen_US
dc.subjectPathwayen_US
dc.subjectHybridsen_US
dc.subjectCanceren_US
dc.titleNovel Substituted Imidazo[2,1-b][1,3,4]Thiadiazole Derivatives: Synthesis, Characterization, Molecular Docking Study, and Investigation of Their In Vitro Antifungal Activitiesen_US
dc.typeArticleen_US

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