Cargando…
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...
Autores principales: | , , , , , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2020
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7570844/ https://www.ncbi.nlm.nih.gov/pubmed/32967192 http://dx.doi.org/10.3390/molecules25184324 |
_version_ | 1783597040800890880 |
---|---|
author | Djuidje, Ernestine Nicaise Durini, Elisa Sciabica, Sabrina Serra, Elena Balzarini, Jan Liekens, Sandra Manfredini, Stefano Vertuani, Silvia Baldisserotto, Anna |
author_facet | Djuidje, Ernestine Nicaise Durini, Elisa Sciabica, Sabrina Serra, Elena Balzarini, Jan Liekens, Sandra Manfredini, Stefano Vertuani, Silvia Baldisserotto, Anna |
author_sort | Djuidje, Ernestine Nicaise |
collection | PubMed |
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(3)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 Candida albicans), antiviral and antiproliferative activity. A Structure-Activity Relationship study indicated compound 10, 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. |
format | Online Article Text |
id | pubmed-7570844 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-75708442020-10-28 Skin Damages—Structure Activity Relationship of Benzimidazole Derivatives Bearing a 5-Membered Ring System Djuidje, Ernestine Nicaise Durini, Elisa Sciabica, Sabrina Serra, Elena Balzarini, Jan Liekens, Sandra Manfredini, Stefano Vertuani, Silvia Baldisserotto, Anna Molecules Article 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(3)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 Candida albicans), antiviral and antiproliferative activity. A Structure-Activity Relationship study indicated compound 10, 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. MDPI 2020-09-21 /pmc/articles/PMC7570844/ /pubmed/32967192 http://dx.doi.org/10.3390/molecules25184324 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Djuidje, Ernestine Nicaise Durini, Elisa Sciabica, Sabrina Serra, Elena Balzarini, Jan Liekens, Sandra Manfredini, Stefano Vertuani, Silvia Baldisserotto, Anna Skin Damages—Structure Activity Relationship of Benzimidazole Derivatives Bearing a 5-Membered Ring System |
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 | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7570844/ https://www.ncbi.nlm.nih.gov/pubmed/32967192 http://dx.doi.org/10.3390/molecules25184324 |
work_keys_str_mv | AT djuidjeernestinenicaise skindamagesstructureactivityrelationshipofbenzimidazolederivativesbearinga5memberedringsystem AT durinielisa skindamagesstructureactivityrelationshipofbenzimidazolederivativesbearinga5memberedringsystem AT sciabicasabrina skindamagesstructureactivityrelationshipofbenzimidazolederivativesbearinga5memberedringsystem AT serraelena skindamagesstructureactivityrelationshipofbenzimidazolederivativesbearinga5memberedringsystem AT balzarinijan skindamagesstructureactivityrelationshipofbenzimidazolederivativesbearinga5memberedringsystem AT liekenssandra skindamagesstructureactivityrelationshipofbenzimidazolederivativesbearinga5memberedringsystem AT manfredinistefano skindamagesstructureactivityrelationshipofbenzimidazolederivativesbearinga5memberedringsystem AT vertuanisilvia skindamagesstructureactivityrelationshipofbenzimidazolederivativesbearinga5memberedringsystem AT baldisserottoanna skindamagesstructureactivityrelationshipofbenzimidazolederivativesbearinga5memberedringsystem |