Urea-sugar and thiourea-sugar diastereomers: synthesis, crystal structure and biological activities

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dc.contributor.authorIsilar, Ozer
dc.contributor.authorBulut, Adnan
dc.contributor.authorTombul, Mustafa
dc.contributor.authorGuner, Adem
dc.contributor.authorSahin, Onur
dc.date.accessioned2026-04-25T14:20:08Z
dc.date.available2026-04-25T14:20:08Z
dc.date.issued2025
dc.departmentSinop Üniversitesi
dc.description.abstractAimsThe principal objective of the conducted study is to synthesize enantiomerically pure a class of sugar-based (thio)ureas (9-12) and to investigate their antiproliferative activities against the A549 (lung cancer), MCF-7 (breast cancer), and PANC1 (human pancreatic cancer) cell lines.Materials and methodsThe synthesis of (thio)urea sugars was performed by two stage procedure. First, the amino sugars (4 and 8) were obtained in three steps (tosylation, substitution and reduction). And secondly, the reaction of 3,5-bis(trifluoromethyl)phenyliso(thio)cyanate with the corresponding amines gave chiral (thio)urea derivatives (9-12). Cell viability was determined in human A549, MCF-7, PANC-1 and noncancer human embryonic kidney (HEK-293) cell lines.ResultsFour chiral sugar (thio)ureas (9-12) were synthesized and screened against the A549, MCF-7, and PANC1 cell lines. Of the four chiral sugar derivatives, the compound 9 not only showed the best anticancer activity in the A549 cell line but also provided the highest normal cell (HEK-293) viability.ConclusionFrom chiral sugar-derived (thio)ureas obtained, the compound 9 was found to be shown the highest activity against A549 cancer cell line. The compound 9, therefore, gave more promising results for future researches as anti-cancer agents. X-ray studies revealed that amide type hydrogens are playing important roles in anti-cancer activities.
dc.description.sponsorshipScientific Research Projects Coordination Unit of Kimath;rimath;kkale University [2021/057]
dc.description.sponsorshipThis work was supported by Scientific Research Projects Coordination Unit of K & imath;r & imath;kkale University. Project number: [2021/057].
dc.identifier.doi10.1080/17568919.2025.2504328
dc.identifier.endpage997
dc.identifier.issn1756-8919
dc.identifier.issn1756-8927
dc.identifier.issue9
dc.identifier.orcid0000-0001-7547-2537
dc.identifier.orcid0000-0001-9322-0325
dc.identifier.orcid0000-0003-3295-3538
dc.identifier.pmid40366764
dc.identifier.scopus2-s2.0-105005416372
dc.identifier.scopusqualityQ2
dc.identifier.startpage991
dc.identifier.urihttps://doi.org/10.1080/17568919.2025.2504328
dc.identifier.urihttps://hdl.handle.net/11486/8394
dc.identifier.volume17
dc.identifier.wosWOS:001487964600001
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherTaylor & Francis Ltd
dc.relation.ispartofFuture Medicinal Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WOS_20260420
dc.subjectUrea
dc.subjectthiourea
dc.subjectsugar
dc.subjectcarbohydrate
dc.subjectcytotoxicity
dc.titleUrea-sugar and thiourea-sugar diastereomers: synthesis, crystal structure and biological activities
dc.typeArticle

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