Bromination and conversion of tetrahydro-1H-indene to bisoxirane with a new approach: synthesis, structural characterization by spectroscopic and theoretical methods, and biological analysis supported by DFT and docking

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dc.authoridÖkten, Salih/0000-0001-9656-1803
dc.contributor.authorYılmaz, Raşit Fikret
dc.contributor.authorErkan, Sultan
dc.contributor.authorÖkten, Salih
dc.contributor.authorTutar, Ahmet
dc.contributor.authorŞahin, Ertan
dc.date.accessioned2025-01-21T16:33:45Z
dc.date.available2025-01-21T16:33:45Z
dc.date.issued2023
dc.departmentKırıkkale Üniversitesi
dc.description.abstractIn this study, a new method for synthesizing diepoxides is proposed. Tetrahydroindene 1 was brominated with NBS in the presence of LiClO4 and acetic acid, resulting in the formation of dibromodiacetate derivatives 2 and 3. Treatment of compounds 2 and 3 with NaOH in methanol produced a mixture of diepoxides 4 and 5. Additionally, direct bromination of tetrahydro-1H-indene yielded tetrabromo octahydroindene isomers 6 and 7. The structures of the compounds were characterized using spectroscopic techniques such as H-1 NMR, C-13 NMR, APT, COSY, and XRD. The new method provides an easy and selective route to access epoxides for the synthesis of various chemicals. This study also highlights the selective formation of endo-exo and exo-exo orientations of the obtained diepoxides, distinguishing it from previous studies. The stability and properties of the stereoisomers were investigated using computational methods, revealing the most stable configurations. Reactive sites in the molecules were identified using contour diagrams and molecular electrostatic potential maps. The anticancer properties of the compounds were evaluated in silico, comparing them to 5-fluorouracil (5-FU) against several cancer cell lines. The compounds exhibited the most effective anticancer activity against MCF-7 cells, with the order of anticancer activities generally determined as 2 > 7 > 3 > 6 > 5 > 4 > 5-FU.
dc.description.sponsorshipSakarya University Scientific Research Projects Coordination Unit [FBYLTEZ 2014-50-01-035]
dc.description.sponsorshipFunding This work was supported by the Sakarya University Scientific Research Projects Coordination Unit (Project Number: FBYLTEZ 2014-50-01-035) .
dc.identifier.doi10.55730/1300-0527.3628
dc.identifier.issn1300-0527
dc.identifier.issue6
dc.identifier.pmid38544714
dc.identifier.scopus2-s2.0-85183100291
dc.identifier.scopusqualityQ3
dc.identifier.trdizinid1220854
dc.identifier.urihttps://doi.org/10.55730/1300-0527.3628
dc.identifier.urihttps://search.trdizin.gov.tr/tr/yayin/detay1220854
dc.identifier.urihttps://hdl.handle.net/20.500.12587/23851
dc.identifier.volume27
dc.identifier.wosWOS:001144116100015
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakTR-Dizin
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherTubitak Scientific & Technological Research Council Turkey
dc.relation.ispartofTurkish Journal of Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/openAccess
dc.snmzKA_20241229
dc.subjectOctahydroindene; dibromodiacetate; diepoxide; tetrabromo octahydroindene; density functional theory; molecular docking
dc.titleBromination and conversion of tetrahydro-1H-indene to bisoxirane with a new approach: synthesis, structural characterization by spectroscopic and theoretical methods, and biological analysis supported by DFT and docking
dc.typeArticle

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