Skin Damages—Structure Activity Relationship of Benzimidazole Derivatives Bearing a 5-Membered Ring System
In the search for scaffolds for multifunctional compounds we investigated the structure activity relationship of a class of benzimidazole derivatives bearing 5-membered ring. The newly synthesized and the already known compounds were divided into three classes that present different substituent at 5...
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MDPI AG
2020-09-01
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author | Ernestine Nicaise Djuidje Elisa Durini Sabrina Sciabica Elena Serra Jan Balzarini Sandra Liekens Stefano Manfredini Silvia Vertuani Anna Baldisserotto |
author_facet | Ernestine Nicaise Djuidje Elisa Durini Sabrina Sciabica Elena Serra Jan Balzarini Sandra Liekens Stefano Manfredini Silvia Vertuani Anna Baldisserotto |
author_sort | Ernestine Nicaise Djuidje |
collection | DOAJ |
description | In the search for scaffolds for multifunctional compounds we investigated the structure activity relationship of a class of benzimidazole derivatives bearing 5-membered ring. The newly synthesized and the already known compounds were divided into three classes that present different substituent at 5 position of the benzimidazole ring (-H, -COOH or –SO<sub>3</sub>H) and different heterocycle at position 2 (thiophene, furan or pyrrole). All the derivatives were synthesized and tested to determine their photoprotective profile against UV rays, in vitro antioxidant capacity against different radicals (DPPH and FRAP test), antifungal inhibitory activity (dermatophytes and <i>Candida albicans</i>), antiviral and antiproliferative activity. A Structure-Activity Relationship study indicated compound <b>10</b>, bearing a pyrrole heterocycle on the benzimidazole ring, as the best multifunctional derivative of the series and as potential candidate for the development of drugs especially in case of melanoma. |
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format | Article |
id | doaj.art-79ce588d2ec24ee8bfeb47fe1bba81d1 |
institution | Directory Open Access Journal |
issn | 1420-3049 |
language | English |
last_indexed | 2024-03-10T16:10:42Z |
publishDate | 2020-09-01 |
publisher | MDPI AG |
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series | Molecules |
spelling | doaj.art-79ce588d2ec24ee8bfeb47fe1bba81d12023-11-20T14:29:38ZengMDPI AGMolecules1420-30492020-09-012518432410.3390/molecules25184324Skin Damages—Structure Activity Relationship of Benzimidazole Derivatives Bearing a 5-Membered Ring SystemErnestine Nicaise Djuidje0Elisa Durini1Sabrina Sciabica2Elena Serra3Jan Balzarini4Sandra Liekens5Stefano Manfredini6Silvia Vertuani7Anna Baldisserotto8Department of Life Sciences and Biotechnology, Master Course in Cosmetic Science and Technologies, University of Ferrara, 44121 Ferrara, ItalyDepartment of Life Sciences and Biotechnology, Master Course in Cosmetic Science and Technologies, University of Ferrara, 44121 Ferrara, ItalyDepartment of Chemical and Pharmaceutical Sciences, University of Ferrara, 44121 Ferrara, ItalyAptuit, An Evotec Company, 37135 Verona, ItalyDepartment of Microbiology and Immunology, KU Leuven, University of Leuven, Rega Institute for Medical Research, Laboratory of Virology and Chemotherapy, B-3000 Leuven, BelgiumDepartment of Microbiology and Immunology, KU Leuven, University of Leuven, Rega Institute for Medical Research, Laboratory of Virology and Chemotherapy, B-3000 Leuven, BelgiumDepartment of Life Sciences and Biotechnology, Master Course in Cosmetic Science and Technologies, University of Ferrara, 44121 Ferrara, ItalyDepartment of Life Sciences and Biotechnology, Master Course in Cosmetic Science and Technologies, University of Ferrara, 44121 Ferrara, ItalyDepartment of Life Sciences and Biotechnology, Master Course in Cosmetic Science and Technologies, University of Ferrara, 44121 Ferrara, ItalyIn the search for scaffolds for multifunctional compounds we investigated the structure activity relationship of a class of benzimidazole derivatives bearing 5-membered ring. The newly synthesized and the already known compounds were divided into three classes that present different substituent at 5 position of the benzimidazole ring (-H, -COOH or –SO<sub>3</sub>H) and different heterocycle at position 2 (thiophene, furan or pyrrole). All the derivatives were synthesized and tested to determine their photoprotective profile against UV rays, in vitro antioxidant capacity against different radicals (DPPH and FRAP test), antifungal inhibitory activity (dermatophytes and <i>Candida albicans</i>), antiviral and antiproliferative activity. A Structure-Activity Relationship study indicated compound <b>10</b>, bearing a pyrrole heterocycle on the benzimidazole ring, as the best multifunctional derivative of the series and as potential candidate for the development of drugs especially in case of melanoma.https://www.mdpi.com/1420-3049/25/18/4324benzimidazoleUV-filtermelanoma |
spellingShingle | Ernestine Nicaise Djuidje Elisa Durini Sabrina Sciabica Elena Serra Jan Balzarini Sandra Liekens Stefano Manfredini Silvia Vertuani Anna Baldisserotto Skin Damages—Structure Activity Relationship of Benzimidazole Derivatives Bearing a 5-Membered Ring System Molecules benzimidazole UV-filter melanoma |
title | Skin Damages—Structure Activity Relationship of Benzimidazole Derivatives Bearing a 5-Membered Ring System |
title_full | Skin Damages—Structure Activity Relationship of Benzimidazole Derivatives Bearing a 5-Membered Ring System |
title_fullStr | Skin Damages—Structure Activity Relationship of Benzimidazole Derivatives Bearing a 5-Membered Ring System |
title_full_unstemmed | Skin Damages—Structure Activity Relationship of Benzimidazole Derivatives Bearing a 5-Membered Ring System |
title_short | Skin Damages—Structure Activity Relationship of Benzimidazole Derivatives Bearing a 5-Membered Ring System |
title_sort | skin damages structure activity relationship of benzimidazole derivatives bearing a 5 membered ring system |
topic | benzimidazole UV-filter melanoma |
url | https://www.mdpi.com/1420-3049/25/18/4324 |
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