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rac- and meso-Cyclohexanoids: Their alpha-, beta-glycosidases, antibacterial, antifungal activities, and molecular docking studies

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dc.contributor.authorKarakilic, Emel
dc.contributor.authorBaran, Sule
dc.contributor.authorOgutcu, Hatice
dc.contributor.authorAKDEMİR, ATİLLA
dc.contributor.authorBaran, Arif
dc.contributor.institutionauthorAKDEMİR, ATİLLA
dc.date.accessioned2020-01-20T20:59:25Z
dc.date.available2020-01-20T20:59:25Z
dc.date.issued2020-01-10T00:00:00Z
dc.description.abstractAn efficient and versatile synthesis method has been postulated for hydroxymethylated rac- and meso-cyclohexanoid derivatives. The synthesis of these stereoisomers was achieved easily with traditional methods using hexahydroisobenzofuran 6, prepared from commercially available cis-hydrophthalic anhydride. The study, involving diastereoselective epoxidation and cis-hydroxylation, was conducted to obtain epoxy-, cis-, and trans-diol-furans 7, 8, and 9. After sulfamic acid-catalyzed ring-opening reaction of the epoxide and furan rings, rac- and meso-tetraacetates 14, 15, and 16 were afforded. Hydrolysis of acetate groups with ammonia in absolute methanol yielded the desired tetrols rac-17, meso-18, and meso-19. All structures, after purification by chromatographic methods and elucidation by spectral techniques, were screened against alpha- and beta-glucosidases. Compounds 7, 8, 10, 17, 18, and 19 were also evaluated for their antibacterial and antifungal activity against some selected synthesized compounds with varying degrees of inhibitory effects on the growth of different pathogenic microorganisms by the well-diffusion method. In addition, Saccharomyces cerevisiae alpha-glucosidase molecular modeling studies were performed for all rac- and meso-compounds 7, 8, 10, 17, 18, and 19.
dc.description.sponsorshipTürkiye Bilimsel Ve Teknolojik Araştırma Kurumu ( Tübitak )
dc.identifier.citationKarakilic E., Baran S., Ogutcu H., AKDEMİR A., Baran A., -rac- and meso-Cyclohexanoids: Their alpha-, beta-glycosidases, antibacterial, antifungal activities, and molecular docking studies-, ARCHIV DER PHARMAZIE, 2020
dc.identifier.doi10.1002/ardp.201900267
dc.identifier.pubmed31922281
dc.identifier.urihttps://openaccess.bezmialem.edu.tr/handle/20.500.12645/13440
dc.identifier.wosWOS:000506452400001
dc.language.isoen
dc.titlerac- and meso-Cyclohexanoids: Their alpha-, beta-glycosidases, antibacterial, antifungal activities, and molecular docking studies
dc.typeArticle
dspace.entity.typePublication
local.avesis.idb36c2fbb-44ac-4ab2-9523-34afdfc7c38f
local.publication.isinternational1
relation.isAuthorOfPublication19bc513a-c695-4e72-ba1d-83b8d6c574c8
relation.isAuthorOfPublication.latestForDiscovery19bc513a-c695-4e72-ba1d-83b8d6c574c8
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