Stereoselective Synthesis of Axially Chiral 5,5′-Linked bis-1-Arylisochromans with Antibacterial Activity

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dc.contributor.authorCzenke, Zoltán
dc.contributor.authorMándi, Attila
dc.contributor.authorFedics, Gergely Miklós
dc.contributor.authorBarta, Roland Albert
dc.contributor.authorKiss-Szikszai, Attila
dc.contributor.authorKurucz-Szabados, Anna
dc.contributor.authorTimári, István
dc.contributor.authorBényei, Attila
dc.contributor.authorKirály, Sándor Balázs
dc.contributor.authorOstorházi, Eszter
dc.contributor.authorZhang, Changsheng
dc.contributor.authorKicsák, Máté
dc.contributor.authorKurtán, Tibor
dc.contributor.authorCzenke Zoltán (1993-) (okleves vegyészmérnök, középiskolai kémiatanár)
dc.contributor.authorKurtán Tibor (1973-) (vegyész, angol szakfordító)
dc.contributor.submitterdepKémiai Intézet -- 724
dc.contributor.submitterdepSzerves Kémiai Tanszék -- 729
dc.contributor.submitterdepTTK
dc.contributor.submitterdepDebreceni Egyetem
dc.date.accessioned2025-08-16T10:59:26Z
dc.date.available2025-08-16T10:59:26Z
dc.date.oa2025-08-17
dc.date.updated2025-08-16T10:59:26Z
dc.description.abstractInspired by naturally occurring bis-isochromans such as penicisteckins, we envisaged the first synthesis of biaryl-type bis-1-arylisochromans containing a stereogenic ortho-trisubstituted biaryl axis. We achieved the stereoselective synthesis of 5,5′-linked heterodimeric bis-isochromans containing both central and axial chirality elements by performing diastereoselective Suzuki–Miyaura biaryl coupling reactions on two optically active 1-arylpropan-2-ol derivatives, followed by two oxa-Pictet–Spengler cyclizations with aryl aldehydes or methoxymethyl chloride. We studied the diastereoselectivity of the cyclization step, separated the stereoisomeric products with chiral preparative HPLC and determined the absolute configuration through a combination of vibrational circular dichroism (VCD), NMR and single-crystal X-ray diffraction analysis. We demonstrated that different aryl groups could be introduced into the two isochroman subunits, since the dimethoxyaryl subunit reacted faster, enabling the two oxa-Pictet–Spengler cyclizations to be performed separately with different aryl aldehydes. We also explored the acid-catalyzed isomerization and oxidation to axially chiral ortho-quinones in order to produce stereoisomeric and oxidized analogs, respectively. We identified the antibacterial activity of our target bis-isochromans against Bacillus subtilis and Enterococcus faecalis with minimum inhibitory concentrations down to 4.0 and 0.5 μg/mL, respectively, which depend on the stereochemistry and substitution pattern of the bis-isochroman skeleton.
dc.description.correctorSZKM
dc.identifier.citationInternational Journal Of Molecular Sciences. -26 : 16 (2025), p. 7777-. -Int. J. Mol. Sci. -1661-6596. -1422-0067
dc.identifier.doi10.3390/ijms26167777
dc.identifier.issn1661-6596. -
dc.identifier.issn1422-0067
dc.identifier.opachttps://ebib.lib.unideb.hu/ebib/CorvinaWeb?action=cclfind&resultview=long&ccltext=idno+BIBFORM131915
dc.identifier.urihttps://hdl.handle.net/2437/396887
dc.identifier.urlhttps://www.mdpi.com/1422-0067/26/16/7777
dc.languageeng
dc.rights.accessopen access article
dc.rights.ownerSzerző
dc.subject.otheridegen nyelvű folyóiratközlemény külföldi lapban
dc.subject.otherheterodimeric biaryl-type axially chiral bis-isochromans
dc.subject.otherstereoselective Suzuki–Miyaura cross-coupling
dc.subject.otherantibacterial
dc.subject.othervibrational circular dichroism
dc.subject.otherchiral induction from central to axial
dc.subject.otherstereoisomeric isochromans with central and axial chirality
dc.subject.otheraxially chiral ortho-quinones
dc.tenderNKFI (K138672) -- Egyéb
dc.tenderDebreceni Egyetem Tudományos Kutatási Alap -- Egyéb
dc.titleStereoselective Synthesis of Axially Chiral 5,5′-Linked bis-1-Arylisochromans with Antibacterial Activity
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