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The synthesis incorporates a new procedure to monochlorinate unsaturated primary amines utilizing <jats:italic>N<\/jats:italic>\u2010chlorosuccinimide, while carefully monitoring the temperature to prevent dichlorination. Furthermore, we successfully isolated highly strained bicyclic aziridines by treating the secondary 3\u2010chloropiperidines 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\u2010chloropiperidine as well as the isolated bicyclic aziridine, proved to be more effective than their tertiary counterpart.<\/jats:p>","DOI":"10.1002\/open.202300181","type":"journal-article","created":{"date-parts":[[2023,12,13]],"date-time":"2023-12-13T08:56:15Z","timestamp":1702457775000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Secondary 3\u2010Chloropiperidines: Powerful Alkylating Agents"],"prefix":"10.1002","volume":"13","author":[{"given":"Mats","family":"Georg","sequence":"first","affiliation":[{"name":"Institute of Organic Chemistry Justus Liebig University Giessen  Heinrich-Buff-Ring 17 35392 Giessen Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Lina Alexandra","family":"Laping","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry Justus Liebig University Giessen  Heinrich-Buff-Ring 17 35392 Giessen Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Veronica","family":"Billo","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry Justus Liebig University Giessen  Heinrich-Buff-Ring 17 35392 Giessen Germany"},{"name":"Department of Pharmaceutical and Pharmacological Sciences University of Padova  Padova Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Barbara","family":"Gatto","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical and Pharmacological Sciences University of Padova  Padova Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Peter","family":"Friedhoff","sequence":"additional","affiliation":[{"name":"Institute of Biochemistry Justus Liebig University Giessen  Heinrich-Buff-Ring 17 35392 Giessen Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1424-3084","authenticated-orcid":false,"given":"Richard","family":"G\u00f6ttlich","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry Justus Liebig University Giessen  Heinrich-Buff-Ring 17 35392 Giessen Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2023,12,13]]},"reference":[{"volume-title":"The cancer handbook","year":"2002","author":"Alison M. 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