Next Article in Journal
Thermal and Electrochemical Properties of Ionic Liquids Bearing Allyl Group with Sulfonate-Based Anions—Application Potential in Epoxy Resin Curing Process
Next Article in Special Issue
Approved Small-Molecule ATP-Competitive Kinases Drugs Containing Indole/Azaindole/Oxindole Scaffolds: R&D and Binding Patterns Profiling
Previous Article in Journal
Bioavailability of Phenolic Compounds in Californian-Style Table Olives with Tunisian Aqueous Olive Leaf Extracts
Previous Article in Special Issue
Spirooxindole: A Versatile Biologically Active Heterocyclic Scaffold
 
 
Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 
Journals
Molecules
Volume 28
Issue 2
10.3390/molecules28020708
molecules-logo
Submit to this Journal Review for this Journal Propose a Special Issue
► Article Menu

Article Menu

share Share announcement Help format_quote Cite question_answer Discuss in SciProfiles
first_page
settings
Order Article Reprints
Font Type:
Arial Georgia Verdana
Font Size:
Aa Aa Aa
Line Spacing:
Column Width:
Background:
Article

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

by
Beata Jasiewicz
1,*,
Karolina Babijczuk
1,
Beata Warżajtis
2,
Urszula Rychlewska
2,
Justyna Starzyk
3,
Grzegorz Cofta
4 and
Lucyna Mrówczyńska
5,*
1
Department of Bioactive Products, Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Poznańskiego 8, 61-614 Poznań, Poland
2
Department of Crystallography, Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Poznańskiego 8, 61-614 Poznań, Poland
3
Department of Soil Science and Microbiology, Faculty of Agronomy, Horticulture, and Bioengineering, University of Life Science, Szydłowska 50, 60-656 Poznań, Poland
4
Department of Wood Chemical Technology, Faculty of Forest and Wood Technology, University of Life Science, Wojska Polskiego 28, 60-637 Poznań, Poland
5
Department of Cell Biology, Faculty of Biology, Adam Mickiewicz University, Uniwersytetu Poznańskiego 6, 61-614 Poznań, Poland
*
Authors to whom correspondence should be addressed.
Molecules 2023, 28(2), 708; https://doi.org/10.3390/molecules28020708
Submission received: 1 December 2022 / Revised: 4 January 2023 / Accepted: 7 January 2023 / Published: 10 January 2023
(This article belongs to the Special Issue Recent Advances in Indole Derivatives in Medicinal and Synthetic Organic Chemistry)
Browse Figures
Versions Notes

Abstract

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.
Keywords: gramine; indole derivatives; antioxidant properties; antibacterial activity; fungicidal properties; chalcogen replacement; S/O equivalence gramine; indole derivatives; antioxidant properties; antibacterial activity; fungicidal properties; chalcogen replacement; S/O equivalence

Share and Cite

MDPI and ACS Style

Jasiewicz, B.; Babijczuk, K.; Warżajtis, B.; Rychlewska, U.; Starzyk, J.; Cofta, G.; Mrówczyńska, L. 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 2023, 28, 708. https://doi.org/10.3390/molecules28020708

AMA Style

Jasiewicz B, Babijczuk K, Warżajtis B, Rychlewska U, Starzyk J, Cofta G, Mrówczyńska L. 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. 2023; 28(2):708. https://doi.org/10.3390/molecules28020708

Chicago/Turabian Style

Jasiewicz, Beata, Karolina Babijczuk, Beata Warżajtis, Urszula Rychlewska, Justyna Starzyk, Grzegorz Cofta, and Lucyna Mrówczyńska. 2023. "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 28, no. 2: 708. https://doi.org/10.3390/molecules28020708

APA Style

Jasiewicz, B., Babijczuk, K., Warżajtis, B., Rychlewska, U., Starzyk, J., Cofta, G., & Mrówczyńska, L. (2023). 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, 28(2), 708. https://doi.org/10.3390/molecules28020708

Article Metrics

Back to TopTop