Indole Derivatives Bearing Imidazole, Benzothiazole-2-Thione or Benzoxazole-2-Thione Moieties—Synthesis, Structure and Evaluation of Their Cytoprotective, Antioxidant, Antibacterial and Fungicidal Activities
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...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-01-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/2/708 |
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| author | Beata Jasiewicz Karolina Babijczuk Beata Warżajtis Urszula Rychlewska Justyna Starzyk Grzegorz Cofta Lucyna Mrówczyńska |
| author_facet | Beata Jasiewicz Karolina Babijczuk Beata Warżajtis Urszula Rychlewska Justyna Starzyk Grzegorz Cofta Lucyna Mrówczyńska |
| author_sort | Beata Jasiewicz |
| collection | DOAJ |
| description | 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: <i>Coriolus versicolor (Cv), Poria placenta (Pp), Coniophora puteana (Cp),</i> and <i>Gloeophyllum trabeum (Gt)</i>. The indole-imidazole derivatives showed the highest antibacterial activity, for which the largest growth-inhibition zones were noted in <i>M. luteus</i> and <i>P. fluorescens</i> cultures. The obtained results may be helpful in the development of selective indole derivatives as effective antioxidants and/or antimicrobial agents. |
| first_indexed | 2024-03-09T11:34:54Z |
| format | Article |
| id | doaj.art-606e4e951abf47e79eb14293132f3663 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T11:34:54Z |
| publishDate | 2023-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-606e4e951abf47e79eb14293132f36632023-11-30T23:43:40ZengMDPI AGMolecules1420-30492023-01-0128270810.3390/molecules28020708Indole Derivatives Bearing Imidazole, Benzothiazole-2-Thione or Benzoxazole-2-Thione Moieties—Synthesis, Structure and Evaluation of Their Cytoprotective, Antioxidant, Antibacterial and Fungicidal ActivitiesBeata Jasiewicz0Karolina Babijczuk1Beata Warżajtis2Urszula Rychlewska3Justyna Starzyk4Grzegorz Cofta5Lucyna Mrówczyńska6Department of Bioactive Products, Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Poznańskiego 8, 61-614 Poznań, PolandDepartment of Bioactive Products, Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Poznańskiego 8, 61-614 Poznań, PolandDepartment of Crystallography, Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Poznańskiego 8, 61-614 Poznań, PolandDepartment of Crystallography, Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Poznańskiego 8, 61-614 Poznań, PolandDepartment of Soil Science and Microbiology, Faculty of Agronomy, Horticulture, and Bioengineering, University of Life Science, Szydłowska 50, 60-656 Poznań, PolandDepartment of Wood Chemical Technology, Faculty of Forest and Wood Technology, University of Life Science, Wojska Polskiego 28, 60-637 Poznań, PolandDepartment of Cell Biology, Faculty of Biology, Adam Mickiewicz University, Uniwersytetu Poznańskiego 6, 61-614 Poznań, PolandIn 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: <i>Coriolus versicolor (Cv), Poria placenta (Pp), Coniophora puteana (Cp),</i> and <i>Gloeophyllum trabeum (Gt)</i>. The indole-imidazole derivatives showed the highest antibacterial activity, for which the largest growth-inhibition zones were noted in <i>M. luteus</i> and <i>P. fluorescens</i> cultures. The obtained results may be helpful in the development of selective indole derivatives as effective antioxidants and/or antimicrobial agents.https://www.mdpi.com/1420-3049/28/2/708gramineindole derivativesantioxidant propertiesantibacterial activityfungicidal propertieschalcogen replacement |
| spellingShingle | Beata Jasiewicz Karolina Babijczuk Beata Warżajtis Urszula Rychlewska Justyna Starzyk Grzegorz Cofta Lucyna Mrówczyńska Indole Derivatives Bearing Imidazole, Benzothiazole-2-Thione or Benzoxazole-2-Thione Moieties—Synthesis, Structure and Evaluation of Their Cytoprotective, Antioxidant, Antibacterial and Fungicidal Activities Molecules gramine indole derivatives antioxidant properties antibacterial activity fungicidal properties chalcogen replacement |
| title | Indole Derivatives Bearing Imidazole, Benzothiazole-2-Thione or Benzoxazole-2-Thione Moieties—Synthesis, Structure and Evaluation of Their Cytoprotective, Antioxidant, Antibacterial and Fungicidal Activities |
| title_full | Indole Derivatives Bearing Imidazole, Benzothiazole-2-Thione or Benzoxazole-2-Thione Moieties—Synthesis, Structure and Evaluation of Their Cytoprotective, Antioxidant, Antibacterial and Fungicidal Activities |
| title_fullStr | Indole Derivatives Bearing Imidazole, Benzothiazole-2-Thione or Benzoxazole-2-Thione Moieties—Synthesis, Structure and Evaluation of Their Cytoprotective, Antioxidant, Antibacterial and Fungicidal Activities |
| title_full_unstemmed | Indole Derivatives Bearing Imidazole, Benzothiazole-2-Thione or Benzoxazole-2-Thione Moieties—Synthesis, Structure and Evaluation of Their Cytoprotective, Antioxidant, Antibacterial and Fungicidal Activities |
| title_short | Indole Derivatives Bearing Imidazole, Benzothiazole-2-Thione or Benzoxazole-2-Thione Moieties—Synthesis, Structure and Evaluation of Their Cytoprotective, Antioxidant, Antibacterial and Fungicidal Activities |
| title_sort | indole derivatives bearing imidazole benzothiazole 2 thione or benzoxazole 2 thione moieties synthesis structure and evaluation of their cytoprotective antioxidant antibacterial and fungicidal activities |
| topic | gramine indole derivatives antioxidant properties antibacterial activity fungicidal properties chalcogen replacement |
| url | https://www.mdpi.com/1420-3049/28/2/708 |
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