Biaryl Sulfonamides Based on the 2-Azabicycloalkane Skeleton-Synthesis and Antiproliferative Activity

Dominika Iwan; Karolina Kamińska; Elżbieta Wojaczyńska; Mateusz Psurski; Joanna Wietrzyk; Marek Daszkiewicz

doi:10.3390/ma13215010

Biaryl Sulfonamides Based on the 2-Azabicycloalkane Skeleton-Synthesis and Antiproliferative Activity

Materials (Basel). 2020 Nov 6;13(21):5010. doi: 10.3390/ma13215010.

Authors

Dominika Iwan¹, Karolina Kamińska¹, Elżbieta Wojaczyńska¹, Mateusz Psurski², Joanna Wietrzyk², Marek Daszkiewicz³

Affiliations

¹ Faculty of Chemistry, Wrocław University of Science and Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland.
² Department of Experimental Oncology, Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Rudolfa Weigla 12, 53-114 Wrocław, Poland.
³ Institute of Low Temperature and Structure Research, Polish Academy of Sciences, Okólna St. 2, 50-422 Wrocław, Poland.

Abstract

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 IC₅₀ values comparable with cisplatin, and some derivatives were found considerably less toxic for nonmalignant cells.

Keywords: antiproliferative activity; azanorbornane derivatives; bicyclic compounds; sulfonamide.