Gabriel-Cromwell aziridination of amino sugars; chiral ferrocenoyl-aziridinyl sugar synthesis and their biological evaluation

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dc.authoridISILAR, OZER/0000-0001-7547-2537
dc.authoridBulut, Adnan/0000-0001-9322-0325
dc.contributor.authorSert, Mustafa
dc.contributor.authorIsilar, Ozer
dc.contributor.authorYaglioglu, Ayse Sahin
dc.contributor.authorBulut, Adnan
dc.date.accessioned2025-01-21T16:41:16Z
dc.date.available2025-01-21T16:41:16Z
dc.date.issued2021
dc.departmentKırıkkale Üniversitesi
dc.description.abstractN-sugar substituted chiral aziridines were synthesized via Gabriel-Cromwell reaction. Novel pure diastereomers of aziridine derivatives (4 diastereomers) were readily obtained in high yields and their structures were confirmed by means of 1H NMR, 13C NMR, FT-IR, Mass and optical rotations. This is, to the best of our knowledge, the unique example of N-sugar aziridine synthesis. Diastereomeric effects for prostate (PC3) and cervix (HeLa) cancers were screened and it has been observed that the epimers bearing the same sugars showed different results against PC3 and HeLa cancer cells. The novel sugar aziridines were investigated as promising prodrug candidates for prostate cancer (PC3) therapy. Moreover, the drug likeness calculations (Lipinski's rule, physicochemical properties, lipophilicity, solubility, pharmacokinetics and bioavailability radar) have indicated that the sugar aziridines can be good candidates as oral drugs.
dc.description.sponsorshipScientific Research Projects Coordina-tion Unit of Krkkale University [2018/032]
dc.description.sponsorshipThis work was supported by Scientific Research Projects Coordina-tion Unit of Krkkale University. Project number: 2018/032.
dc.identifier.doi10.1016/j.carres.2021.108430
dc.identifier.issn0008-6215
dc.identifier.issn1873-426X
dc.identifier.pmid34488002
dc.identifier.scopus2-s2.0-85114184747
dc.identifier.scopusqualityQ2
dc.identifier.urihttps://doi.org/10.1016/j.carres.2021.108430
dc.identifier.urihttps://hdl.handle.net/20.500.12587/24854
dc.identifier.volume509
dc.identifier.wosWOS:000701954000010
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherElsevier Sci Ltd
dc.relation.ispartofCarbohydrate Research
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_20241229
dc.subjectAmino sugar; Aziridine; Ferrocene; PC3; HeLa; Drug likeness
dc.titleGabriel-Cromwell aziridination of amino sugars; chiral ferrocenoyl-aziridinyl sugar synthesis and their biological evaluation
dc.typeArticle

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