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Biaryl Sulfonamides Based on the 2-Azabicycloalkane Skeleton—Synthesis and Antiproliferative Activity
In a search for new, selective antitumor agents, we prepared a series of sulfonamides built on bicyclic scaffolds of 2-azabicyclo(2.2.1)heptane and 2-azabicyclo(3.2.1)octane. To this end, aza-Diels–Alder cycloadducts were converted into amines bearing 2-azanorbornane or a bridged azepane skeleton; t...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7664408/ https://www.ncbi.nlm.nih.gov/pubmed/33172089 http://dx.doi.org/10.3390/ma13215010 |
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author | Iwan, Dominika Kamińska, Karolina Wojaczyńska, Elżbieta Psurski, Mateusz Wietrzyk, Joanna Daszkiewicz, Marek |
author_facet | Iwan, Dominika Kamińska, Karolina Wojaczyńska, Elżbieta Psurski, Mateusz Wietrzyk, Joanna Daszkiewicz, Marek |
author_sort | Iwan, Dominika |
collection | PubMed |
description | In a search for new, selective antitumor agents, we prepared a series of sulfonamides built on bicyclic scaffolds of 2-azabicyclo(2.2.1)heptane and 2-azabicyclo(3.2.1)octane. To this end, aza-Diels–Alder cycloadducts were converted into amines bearing 2-azanorbornane or a bridged azepane skeleton; their treatment with sulfonyl chlorides containing biaryl moieties led to the title compounds. The study of antiproliferative activity of the new agents showed that some of them inhibited the growth of chosen cell lines with the IC(50) values comparable with cisplatin, and some derivatives were found considerably less toxic for nonmalignant cells. |
format | Online Article Text |
id | pubmed-7664408 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-76644082020-11-14 Biaryl Sulfonamides Based on the 2-Azabicycloalkane Skeleton—Synthesis and Antiproliferative Activity Iwan, Dominika Kamińska, Karolina Wojaczyńska, Elżbieta Psurski, Mateusz Wietrzyk, Joanna Daszkiewicz, Marek Materials (Basel) Article In a search for new, selective antitumor agents, we prepared a series of sulfonamides built on bicyclic scaffolds of 2-azabicyclo(2.2.1)heptane and 2-azabicyclo(3.2.1)octane. To this end, aza-Diels–Alder cycloadducts were converted into amines bearing 2-azanorbornane or a bridged azepane skeleton; their treatment with sulfonyl chlorides containing biaryl moieties led to the title compounds. The study of antiproliferative activity of the new agents showed that some of them inhibited the growth of chosen cell lines with the IC(50) values comparable with cisplatin, and some derivatives were found considerably less toxic for nonmalignant cells. MDPI 2020-11-06 /pmc/articles/PMC7664408/ /pubmed/33172089 http://dx.doi.org/10.3390/ma13215010 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 Iwan, Dominika Kamińska, Karolina Wojaczyńska, Elżbieta Psurski, Mateusz Wietrzyk, Joanna Daszkiewicz, Marek Biaryl Sulfonamides Based on the 2-Azabicycloalkane Skeleton—Synthesis and Antiproliferative Activity |
title | Biaryl Sulfonamides Based on the 2-Azabicycloalkane Skeleton—Synthesis and Antiproliferative Activity |
title_full | Biaryl Sulfonamides Based on the 2-Azabicycloalkane Skeleton—Synthesis and Antiproliferative Activity |
title_fullStr | Biaryl Sulfonamides Based on the 2-Azabicycloalkane Skeleton—Synthesis and Antiproliferative Activity |
title_full_unstemmed | Biaryl Sulfonamides Based on the 2-Azabicycloalkane Skeleton—Synthesis and Antiproliferative Activity |
title_short | Biaryl Sulfonamides Based on the 2-Azabicycloalkane Skeleton—Synthesis and Antiproliferative Activity |
title_sort | biaryl sulfonamides based on the 2-azabicycloalkane skeleton—synthesis and antiproliferative activity |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7664408/ https://www.ncbi.nlm.nih.gov/pubmed/33172089 http://dx.doi.org/10.3390/ma13215010 |
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