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Indole Derivatives Bearing Imidazole, Benzothiazole-2-Thione or Benzoxazole-2-Thione Moieties—Synthesis, Structure and Evaluation of Their Cytoprotective, Antioxidant, Antibacterial and Fungicidal Activities

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cris.virtual.author-orcid0000-0002-8295-5980
cris.virtual.author-orcid0000-0002-5472-6128
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cris.virtualsource.author-orcid1e124447-5576-474f-b662-b24f9118c42d
cris.virtualsource.author-orcid62b18ab5-eecf-4f1a-8afd-5cf500b29bf9
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dc.abstract.enIn the search for new bioactive compounds, a methodology based on combining two molecules with biological properties into a new hybrid molecule was used to design and synthesize of a series of ten indole derivatives bearing imidazole, benzothiazole-2-thione, or benzoxazole-2-thione moieties at the C-3 position. The compounds were spectroscopically characterized and tested for their antioxidant, antibacterial, and fungicidal activities. The crystal structures were determined for five of them. Comparison of the closely related structures containing either benzothiazole-2-thione or benzoxazole-2-thione clearly shows that the replacement of -S- and -O- ring atoms modify molecular conformation in the crystal, changes intermolecular interactions, and has a severe impact on biological activity. The results indicate that indole-imidazole derivatives with alkyl substituent exhibit an excellent cytoprotective effect against AAPH-induced oxidative hemolysis and act as effective ferrous ion chelating agents. The indole-imidazole compound with chlorine atoms inhibited the growth of fungal strains: Coriolus versicolor (Cv), Poria placenta (Pp), Coniophora puteana (Cp), and Gloeophyllum trabeum (Gt). The indole-imidazole derivatives showed the highest antibacterial activity, for which the largest growth-inhibition zones were noted in M. luteus and P. fluorescens cultures. The obtained results may be helpful in the development of selective indole derivatives as effective antioxidants and/or antimicrobial agents.
dc.affiliationWydział Rolnictwa, Ogrodnictwa i Bioinżynierii
dc.affiliationWydział Leśny i Technologii Drewna
dc.affiliation.instituteKatedra Gleboznawstwa i Mikrobiologii
dc.affiliation.instituteKatedra Chemicznej Technologii Drewna
dc.contributor.authorJasiewicz, Beata
dc.contributor.authorBabijczuk, Karolina
dc.contributor.authorWarżajtis, Beata
dc.contributor.authorRychlewska, Urszula
dc.contributor.authorStarzyk, Justyna
dc.contributor.authorCofta, Grzegorz
dc.contributor.authorMrówczyńska, Lucyna
dc.date.access2026-04-13
dc.date.accessioned2026-04-13T09:39:55Z
dc.date.available2026-04-13T09:39:55Z
dc.date.copyright2023-01-10
dc.date.issued2023
dc.description.abstract<jats:p>In the search for new bioactive compounds, a methodology based on combining two molecules with biological properties into a new hybrid molecule was used to design and synthesize of a series of ten indole derivatives bearing imidazole, benzothiazole-2-thione, or benzoxazole-2-thione moieties at the C-3 position. The compounds were spectroscopically characterized and tested for their antioxidant, antibacterial, and fungicidal activities. The crystal structures were determined for five of them. Comparison of the closely related structures containing either benzothiazole-2-thione or benzoxazole-2-thione clearly shows that the replacement of -S- and -O- ring atoms modify molecular conformation in the crystal, changes intermolecular interactions, and has a severe impact on biological activity. The results indicate that indole-imidazole derivatives with alkyl substituent exhibit an excellent cytoprotective effect against AAPH-induced oxidative hemolysis and act as effective ferrous ion chelating agents. The indole-imidazole compound with chlorine atoms inhibited the growth of fungal strains: Coriolus versicolor (Cv), Poria placenta (Pp), Coniophora puteana (Cp), and Gloeophyllum trabeum (Gt). The indole-imidazole derivatives showed the highest antibacterial activity, for which the largest growth-inhibition zones were noted in M. luteus and P. fluorescens cultures. The obtained results may be helpful in the development of selective indole derivatives as effective antioxidants and/or antimicrobial agents.</jats:p>
dc.description.accesstimeat_publication
dc.description.bibliographyil., bibliogr.
dc.description.financepublication_nocost
dc.description.financecost0,00
dc.description.if4,2
dc.description.number2
dc.description.points140
dc.description.versionfinal_published
dc.description.volume28
dc.identifier.doi10.3390/molecules28020708
dc.identifier.issn1420-3049
dc.identifier.urihttps://sciencerep.up.poznan.pl/handle/item/8072
dc.identifier.weblinkhttps://www.mdpi.com/1420-3049/28/2/708
dc.languageen
dc.relation.ispartofMolecules
dc.relation.pagesart. 708
dc.rightsCC-BY
dc.sciencecloudnosend
dc.share.typeOPEN_JOURNAL
dc.subject.engramine
dc.subject.enindole derivatives
dc.subject.enantioxidant properties
dc.subject.enantibacterial activity
dc.subject.enfungicidal properties
dc.subject.enchalcogen replacement
dc.subject.enS/O equivalence
dc.titleIndole Derivatives Bearing Imidazole, Benzothiazole-2-Thione or Benzoxazole-2-Thione Moieties—Synthesis, Structure and Evaluation of Their Cytoprotective, Antioxidant, Antibacterial and Fungicidal Activities
dc.title.volumeSpecial Issue Recent Advances in Indole Derivatives in Medicinal and Synthetic Organic Chemistry
dc.typeJournalArticle
dspace.entity.typePublication
oaire.citation.issue2
oaire.citation.volume28