Enantioselective synthesis of tranylcypromine analogues as lysine demethylase (LSD1) inhibitors

Hanae Benelkebir, Christopher Hodgkinson, Patrick J. Duriez, Annette L. Hayden, Rosemary A. Bulleid, Simon J. Crabb, Graham Packham, A Ganesan

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Asymmetric cyclopropanation of styrenes by tert-butyl diazoacetate followed by ester hydrolysis and Curtius rearrangement gave a series of tranylcypromine analogues as single enantiomers. The o,- m- and p-bromo analogues were all more active than tranylcypromine in a LSD1 enzyme assay. The m- and p-bromo analogues were micromolar growth inhibitors of the LNCaP prostate cancer cell line as were the corresponding biphenyl analogues prepared from the bromide by Suzuki crosscoupling.
Original languageEnglish
Pages (from-to)3709-3716
Number of pages8
JournalBioorganic & Medicinal Chemistry
Issue number12
Publication statusPublished - 15 Jun 2011

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