Secondary 3-Chloropiperidines: Powerful Alkylating Agents

dc.contributor.authorGeorg, Mats
dc.contributor.authorLaping, Lina Alexandra
dc.contributor.authorBillo, Veronica
dc.contributor.authorGatto, Barbara
dc.contributor.authorFriedhoff, Peter
dc.contributor.authorGöttlich, Richard
dc.date.accessioned2024-02-28T12:13:18Z
dc.date.available2024-02-28T12:13:18Z
dc.date.issued2023
dc.description.abstractIn 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.
dc.identifier.urihttps://jlupub.ub.uni-giessen.de//handle/jlupub/19046
dc.identifier.urihttp://dx.doi.org/10.22029/jlupub-18407
dc.language.isoen
dc.rightsNamensnennung 4.0 International
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/
dc.subject.ddcddc:540
dc.titleSecondary 3-Chloropiperidines: Powerful Alkylating Agents
dc.typearticle
local.affiliationFB 08 - Biologie und Chemie
local.source.articlenumbere202300181
local.source.epage9
local.source.journaltitleChemistryOpen
local.source.spage1
local.source.urihttps://doi.org/10.1002/open.202300181

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