Cargando…

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...

Descripción completa

Detalles Bibliográficos
Autores principales: Iwan, Dominika, Kamińska, Karolina, Wojaczyńska, Elżbieta, Psurski, Mateusz, Wietrzyk, Joanna, Daszkiewicz, Marek
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
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
_version_ 1783609840854106112
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
work_keys_str_mv AT iwandominika biarylsulfonamidesbasedonthe2azabicycloalkaneskeletonsynthesisandantiproliferativeactivity
AT kaminskakarolina biarylsulfonamidesbasedonthe2azabicycloalkaneskeletonsynthesisandantiproliferativeactivity
AT wojaczynskaelzbieta biarylsulfonamidesbasedonthe2azabicycloalkaneskeletonsynthesisandantiproliferativeactivity
AT psurskimateusz biarylsulfonamidesbasedonthe2azabicycloalkaneskeletonsynthesisandantiproliferativeactivity
AT wietrzykjoanna biarylsulfonamidesbasedonthe2azabicycloalkaneskeletonsynthesisandantiproliferativeactivity
AT daszkiewiczmarek biarylsulfonamidesbasedonthe2azabicycloalkaneskeletonsynthesisandantiproliferativeactivity