Georg, MatsMatsGeorgLaping, Lina AlexandraLina AlexandraLapingBillo, VeronicaVeronicaBilloGatto, BarbaraBarbaraGattoFriedhoff, PeterPeterFriedhoffGöttlich, RichardRichardGöttlich2024-02-282024-02-282023https://jlupub.ub.uni-giessen.de/handle/jlupub/19046http://dx.doi.org/10.22029/jlupub-18407In previous works, we demonstrated that tertiary 3-chloropiperidines are potent chemotherapeutics, alkylating the DNA through the formation of bicyclic aziridinium ions. Herein, we report the synthesis of novel secondary 3-chloropiperidine analogues. The synthesis incorporates a new procedure to monochlorinate unsaturated primary amines utilizing N-chlorosuccinimide, while carefully monitoring the temperature to prevent dichlorination. Furthermore, we successfully isolated highly strained bicyclic aziridines by treating the secondary 3-chloropiperidines with a sufficient amount of base. We conclude this work with a DNA cleavage assay as a proof of principle, comparing our previously known substrates to the novel compounds. In this, the secondary 3-chloropiperidine as well as the isolated bicyclic aziridine, proved to be more effective than their tertiary counterpart.enNamensnennung 4.0 Internationalddc:540