Secondary 3-Chloropiperidines: Powerful Alkylating Agents
dc.contributor.author | Georg, Mats | |
dc.contributor.author | Laping, Lina Alexandra | |
dc.contributor.author | Billo, Veronica | |
dc.contributor.author | Gatto, Barbara | |
dc.contributor.author | Friedhoff, Peter | |
dc.contributor.author | Göttlich, Richard | |
dc.date.accessioned | 2024-02-28T12:13:18Z | |
dc.date.available | 2024-02-28T12:13:18Z | |
dc.date.issued | 2023 | |
dc.description.abstract | In 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.uri | https://jlupub.ub.uni-giessen.de//handle/jlupub/19046 | |
dc.identifier.uri | http://dx.doi.org/10.22029/jlupub-18407 | |
dc.language.iso | en | |
dc.rights | Namensnennung 4.0 International | |
dc.rights.uri | https://creativecommons.org/licenses/by/4.0/ | |
dc.subject.ddc | ddc:540 | |
dc.title | Secondary 3-Chloropiperidines: Powerful Alkylating Agents | |
dc.type | article | |
local.affiliation | FB 08 - Biologie und Chemie | |
local.source.articlenumber | e202300181 | |
local.source.epage | 9 | |
local.source.journaltitle | ChemistryOpen | |
local.source.spage | 1 | |
local.source.uri | https://doi.org/10.1002/open.202300181 |
Dateien
Originalbündel
1 - 1 von 1
Lade...
- Name:
- 10.1002_open.202300181.pdf
- Größe:
- 2.15 MB
- Format:
- Adobe Portable Document Format
- Beschreibung: