Novel 2-amino-1,3,4-thiadiazoles and their acyl derivatives: Synthesis, structural characterization, molecular docking studies and comparison of experimental and computational results

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dc.authoridkarakurt, tuncay/0000-0001-6944-9883
dc.authoridTAHTACI, HAKAN/0000-0002-1557-6315
dc.contributor.authorEr, Mustafa
dc.contributor.authorIsildak, Gamze
dc.contributor.authorTahtaci, Hakan
dc.contributor.authorKarakurt, Tuncay
dc.date.accessioned2024-09-29T16:00:26Z
dc.date.available2024-09-29T16:00:26Z
dc.date.issued2016
dc.departmentKarabük Üniversitesien_US
dc.description.abstractThis 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.en_US
dc.description.sponsorshipKarabtik University [KBU-BAP-14/1-YL-012]; National Center for High Performance Computing of Turkey (UHeM) [1002742013]en_US
dc.description.sponsorshipThe financial support under the contract (KBU-BAP-14/1-YL-012) from the Karabtik University is gratefully acknowledged. In addition, computing resources used in this work were provided by the National Center for High Performance Computing of Turkey (UHeM) under grant number 1002742013.en_US
dc.identifier.doi10.1016/j.molstruc.2016.01.045
dc.identifier.endpage113en_US
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.scopus2-s2.0-84955285098en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.startpage102en_US
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2016.01.045
dc.identifier.urihttps://hdl.handle.net/20.500.14619/5125
dc.identifier.volume1110en_US
dc.identifier.wosWOS:000371652900013en_US
dc.identifier.wosqualityQ3en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherElsevier Science Bven_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.subject2-amino-1,3,4-thiadiazoleen_US
dc.subjectCrystal structureen_US
dc.subjectNMRen_US
dc.subjectB3LYPen_US
dc.titleNovel 2-amino-1,3,4-thiadiazoles and their acyl derivatives: Synthesis, structural characterization, molecular docking studies and comparison of experimental and computational resultsen_US
dc.typeArticleen_US

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