Regio- and stereospecific synthesis of rac-carbasugar-based cyclohexane pentols; Investigations of their α- and β-glucosidase inhibitions

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dc.authoridCOL, Sumeyye/0000-0003-2932-9718
dc.contributor.authorKarakilic, Emel
dc.contributor.authorDurmus, Sumeyye
dc.contributor.authorSevmezler, Sedat
dc.contributor.authorSahin, Onur
dc.contributor.authorBaran, Arif
dc.date.accessioned2025-03-23T19:41:55Z
dc.date.available2025-03-23T19:41:55Z
dc.date.issued2018
dc.departmentSinop Üniversitesi
dc.description.abstractIn the present study, (3aR,7aS)-1,3,3a,4,7,7a-hexahydroisobenzofuran was submitted to photooxygenation and two isomeric hydroperoxides were successfully obtained. Without any further purification, reduction of the hydroperoxides with titanium tetraisopropoxide catalyzed by dimethyl sulfide gave two alcohol isomers in high yields. After acetylation of alcohol with Ac2O in pyridine, epoxidation reaction of formed monoacetates with mCPBA, then chromatographed and followed by hydrolysis of the acetate groups with NH3 in CH3OH resulted in the formation of epoxy alcohol isomers respectively. These epoxy alcohol isomers were subjected to trans-dihydroxylation reaction with acid (H2SO4) in the presence of water to afford triols. Acetylation of the free hydroxyl groups produced benzofuran triacetates in high yields. Ring-opening reaction of furan triacetates with sulfamic acid catalyzed in the presence of acetic acid/acetic anhydrate and subsequently hydrolysis of the acetate groups with ammonia gave the targeted cyclohexane carbasugar-based pentols. All products were separated and purified by chromatographic and crystallographic methods. Structural analyses of all compounds were conducted by spectral techniques including NMR and X-ray analyses. The biological inhibition activity of the target compounds was tested against glycosidase enzymes, alpha- and beta-glucosidase.
dc.description.sponsorshipScientific and Technological Research Council of Turkey - Turkey (TUBITAK) [TBAG-113Z699, KBAG-115Z446]; Unit of Scientific Research Projects of Sakarya University - Turkey (SAU-BAP) [2014-02-03-003]
dc.description.sponsorshipThe authors are grateful to the Scientific and Technological Research Council of Turkey - Turkey (TUBITAK, Grand No. TBAG-113Z699 and KBAG-115Z446) and the Unit of Scientific Research Projects of Sakarya University - Turkey (SAU-BAP, Grand No. 2014-02-03-003) for financial support of this work and Scientific and Technological Research Application and Research Center, Sinop University, Turkey, for the use of the Bruker D8 QUEST diffractometer. This work conducted at Organic Chemistry Research Laboratory at Sakarya University.
dc.identifier.doi10.1016/j.bmc.2018.07.021
dc.identifier.endpage4287
dc.identifier.issn0968-0896
dc.identifier.issn1464-3391
dc.identifier.issue14
dc.identifier.pmid30031655
dc.identifier.scopus2-s2.0-85049966152
dc.identifier.scopusqualityQ1
dc.identifier.startpage4276
dc.identifier.urihttps://doi.org/10.1016/j.bmc.2018.07.021
dc.identifier.urihttps://hdl.handle.net/11486/6682
dc.identifier.volume26
dc.identifier.wosWOS:000440942100045
dc.identifier.wosqualityQ1
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherPergamon-Elsevier Science Ltd
dc.relation.ispartofBioorganic & Medicinal Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WOS_20250323
dc.subjectene Reaction
dc.subjectCyclitol
dc.subjectCarbasugar
dc.subjectBiological activity
dc.titleRegio- and stereospecific synthesis of rac-carbasugar-based cyclohexane pentols; Investigations of their α- and β-glucosidase inhibitions
dc.typeArticle

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