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

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dc.authoridkarakurt, tuncay/0000-0001-6944-9883
dc.authoridTAHTACI, HAKAN/0000-0002-1557-6315
dc.authoridEce, Abdulilah/0000-0002-3087-5145
dc.contributor.authorEr, Mustafa
dc.contributor.authorErguven, Bugracan
dc.contributor.authorTahtaci, Hakan
dc.contributor.authorOnaran, Abdurrahman
dc.contributor.authorKarakurt, Tuncay
dc.contributor.authorEce, Abdulilah
dc.date.accessioned2024-09-29T15:50:54Z
dc.date.available2024-09-29T15:50:54Z
dc.date.issued2017
dc.departmentKarabük Üniversitesien_US
dc.description.abstractThe 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.en_US
dc.description.sponsorshipKarabuk University [KBU-BAP-15/2-YL-017]en_US
dc.description.sponsorshipThe financial support under the contract (KBU-BAP-15/2-YL-017) from Karabuk University is gratefully acknowledged.en_US
dc.identifier.doi10.1007/s00044-017-1782-4
dc.identifier.endpage630en_US
dc.identifier.issn1054-2523
dc.identifier.issn1554-8120
dc.identifier.issue3en_US
dc.identifier.scopus2-s2.0-85009292299en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.startpage615en_US
dc.identifier.urihttps://doi.org/10.1007/s00044-017-1782-4
dc.identifier.urihttps://hdl.handle.net/20.500.14619/3793
dc.identifier.volume26en_US
dc.identifier.wosWOS:000394322200009en_US
dc.identifier.wosqualityQ4en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherSpringer Birkhauseren_US
dc.relation.ispartofMedicinal Chemistry Researchen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subject2-Amino-[1,3,4]thiadiazoleen_US
dc.subjectImidazo[2,1-b][1,3,4]thiadiazoleen_US
dc.subjectPhenacyl bromideen_US
dc.subjectMolecular dockingen_US
dc.subjectAntifungal activityen_US
dc.subjectSARen_US
dc.titleSynthesis, characterization, preliminary SAR and molecular docking study of some novel substituted imidazo[2,1-b][1,3,4]thiadiazole derivatives as antifungal agentsen_US
dc.typeArticleen_US

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