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

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dc.authoridkarakurt, tuncay/0000-0001-6944-9883
dc.authoridTAHTACI, HAKAN/0000-0002-1557-6315
dc.contributor.authorEr, Mustafa
dc.contributor.authorOzer, Arif
dc.contributor.authorDirekel, Sahin
dc.contributor.authorKarakurt, Tuncay
dc.contributor.authorTahtaci, Hakan
dc.date.accessioned2024-09-29T16:00:26Z
dc.date.available2024-09-29T16:00:26Z
dc.date.issued2019
dc.departmentKarabük Üniversitesien_US
dc.description.abstractIn 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.en_US
dc.description.sponsorshipKarabuk University [KBUBAP-17-YL-038]en_US
dc.description.sponsorshipThe financial support by the Karabuk University (Project ID Number: KBUBAP-17-YL-038) is gratefully acknowledged.en_US
dc.identifier.doi10.1016/j.molstruc.2019.05.104
dc.identifier.endpage296en_US
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.scopus2-s2.0-85066997421en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.startpage284en_US
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2019.05.104
dc.identifier.urihttps://hdl.handle.net/20.500.14619/5132
dc.identifier.volume1194en_US
dc.identifier.wosWOS:000471778600031en_US
dc.identifier.wosqualityQ3en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherElsevieren_US
dc.relation.ispartofJournal of Molecular Structureen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectBenzothiazoleen_US
dc.subjectImidazo[2,1-b][1,3,4]thiadiazoleen_US
dc.subjectBiological activityen_US
dc.subjectMolecular dockingen_US
dc.subjectHOMOen_US
dc.titleNovel 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 activitiesen_US
dc.typeArticleen_US

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