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Design and Synthesis of New 1,3,5‐Trisubstituted Triazines for the Treatment of Cancer and Inflammation
Low‐molecular‐weight synthetic molecules 1 with the general 2‐(fluorophenylamino)‐4,6‐disubstituted 1,3,5‐triazine structure and showing anti‐inflammatory and anticancer activities were explored. Structure–activity relationship studies demonstrated the importance of the aminopentyl chain, the 3‐ or...
Autores principales: | , , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6148406/ https://www.ncbi.nlm.nih.gov/pubmed/30258746 http://dx.doi.org/10.1002/open.201800136 |
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author | Zacharie, Boulos Abbott, Shaun D. Duceppe, Jean‐Simon Gagnon, Lyne Grouix, Brigitte Geerts, Lilianne Gervais, Liette Sarra‐Bournet, François Perron, Valérie Wilb, Nicole Penney, Christopher L. Laurin, Pierre |
author_facet | Zacharie, Boulos Abbott, Shaun D. Duceppe, Jean‐Simon Gagnon, Lyne Grouix, Brigitte Geerts, Lilianne Gervais, Liette Sarra‐Bournet, François Perron, Valérie Wilb, Nicole Penney, Christopher L. Laurin, Pierre |
author_sort | Zacharie, Boulos |
collection | PubMed |
description | Low‐molecular‐weight synthetic molecules 1 with the general 2‐(fluorophenylamino)‐4,6‐disubstituted 1,3,5‐triazine structure and showing anti‐inflammatory and anticancer activities were explored. Structure–activity relationship studies demonstrated the importance of the aminopentyl chain, the 3‐ or 4‐fluorophenylaniline component, and the presence of at least one substituent, such as a tyramine moiety, attached directly to the triazine ring as essential for good activity. These compounds, represented by leads 4‐{2‐[4‐(5‐Aminopentylamino)‐6‐(3‐fluorophenylamino)‐1,3,5‐triazin‐2‐ylamino]ethyl}phenol (6) and 4‐{2‐[4‐(5‐Aminopentylamino)‐6‐(4‐fluorophenylamino)‐1,3,5‐triazin‐2‐ylamino]ethyl}phenol (10), displayed moderate and significant in vitro and in vivo dual activities, respectively, and address the molecular link between inflammation and cancer. Compound 10 demonstrated significant antitumor efficacy upon administration by the oral and intravenous routes in several animal models. This class of triazine compounds is new, safe, and nontoxic and offers a novel approach to the treatment of inflammation and cancer. |
format | Online Article Text |
id | pubmed-6148406 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-61484062018-09-26 Design and Synthesis of New 1,3,5‐Trisubstituted Triazines for the Treatment of Cancer and Inflammation Zacharie, Boulos Abbott, Shaun D. Duceppe, Jean‐Simon Gagnon, Lyne Grouix, Brigitte Geerts, Lilianne Gervais, Liette Sarra‐Bournet, François Perron, Valérie Wilb, Nicole Penney, Christopher L. Laurin, Pierre ChemistryOpen Full Papers Low‐molecular‐weight synthetic molecules 1 with the general 2‐(fluorophenylamino)‐4,6‐disubstituted 1,3,5‐triazine structure and showing anti‐inflammatory and anticancer activities were explored. Structure–activity relationship studies demonstrated the importance of the aminopentyl chain, the 3‐ or 4‐fluorophenylaniline component, and the presence of at least one substituent, such as a tyramine moiety, attached directly to the triazine ring as essential for good activity. These compounds, represented by leads 4‐{2‐[4‐(5‐Aminopentylamino)‐6‐(3‐fluorophenylamino)‐1,3,5‐triazin‐2‐ylamino]ethyl}phenol (6) and 4‐{2‐[4‐(5‐Aminopentylamino)‐6‐(4‐fluorophenylamino)‐1,3,5‐triazin‐2‐ylamino]ethyl}phenol (10), displayed moderate and significant in vitro and in vivo dual activities, respectively, and address the molecular link between inflammation and cancer. Compound 10 demonstrated significant antitumor efficacy upon administration by the oral and intravenous routes in several animal models. This class of triazine compounds is new, safe, and nontoxic and offers a novel approach to the treatment of inflammation and cancer. John Wiley and Sons Inc. 2018-09-21 /pmc/articles/PMC6148406/ /pubmed/30258746 http://dx.doi.org/10.1002/open.201800136 Text en © 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made. |
spellingShingle | Full Papers Zacharie, Boulos Abbott, Shaun D. Duceppe, Jean‐Simon Gagnon, Lyne Grouix, Brigitte Geerts, Lilianne Gervais, Liette Sarra‐Bournet, François Perron, Valérie Wilb, Nicole Penney, Christopher L. Laurin, Pierre Design and Synthesis of New 1,3,5‐Trisubstituted Triazines for the Treatment of Cancer and Inflammation |
title | Design and Synthesis of New 1,3,5‐Trisubstituted Triazines for the Treatment of Cancer and Inflammation |
title_full | Design and Synthesis of New 1,3,5‐Trisubstituted Triazines for the Treatment of Cancer and Inflammation |
title_fullStr | Design and Synthesis of New 1,3,5‐Trisubstituted Triazines for the Treatment of Cancer and Inflammation |
title_full_unstemmed | Design and Synthesis of New 1,3,5‐Trisubstituted Triazines for the Treatment of Cancer and Inflammation |
title_short | Design and Synthesis of New 1,3,5‐Trisubstituted Triazines for the Treatment of Cancer and Inflammation |
title_sort | design and synthesis of new 1,3,5‐trisubstituted triazines for the treatment of cancer and inflammation |
topic | Full Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6148406/ https://www.ncbi.nlm.nih.gov/pubmed/30258746 http://dx.doi.org/10.1002/open.201800136 |
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