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

Basit Öğe Kaydı
dc.authorid0000-0001-6744-929Xtr
dc.contributor.authorYILMAZ, R. F.
dc.contributor.authorErkan Sultan
dc.contributor.authorÖKTEN, S.
dc.contributor.authorTutar, A.
dc.contributor.authorŞAHİN, E.
dc.date.accessioned2024-03-07T10:10:25Z
dc.date.available2024-03-07T10:10:25Z
dc.date.issued2023tr
dc.departmentFen Fakültesitr
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 1H NMR, 13C 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.tr
dc.identifier.citationYILMAZ, R. F., Erkan, S., ÖKTEN, S., Tutar, A., & ŞAHİN, E. (2023). 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. Turkish Journal of Chemistry, 47(6), 1459-1478.tr
dc.identifier.doi10.55730/1300-0527.3628en_US
dc.identifier.issue6tr
dc.identifier.pmid38544714en_US
dc.identifier.scopus2-s2.0-85183100291en_US
dc.identifier.scopusqualityN/A
dc.identifier.trdizinid1220854en_US
dc.identifier.urihttps://journals.tubitak.gov.tr/chem/vol47/iss6/15/
dc.identifier.urihttps://hdl.handle.net/20.500.12418/14893
dc.identifier.volume47tr
dc.identifier.wosWOS:001144116100015en_US
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.indekslendigikaynakTR-Dizinen_US
dc.indekslendigikaynakPubMeden_US
dc.language.isoenen_US
dc.publisherTÜBİTAKtr
dc.relation.ispartofTurkish Journal of Chemistryen_US
dc.relation.publicationcategoryUluslararası Hakemli Dergide Makale - Başka Kurum Yazarıtr
dc.rightsinfo:eu-repo/semantics/openAccesstr
dc.subjectOctahydroindene, dibromodiacetate, diepoxide, tetrabromo octahydroindene, density functional theory, molecular dockingtr
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 dockingen_US
dc.typeArticleen_US

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