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

Benelkebir, Hanae, Hodgkinson, Christopher, Duriez, Patrick J., Hayden, Annette L., Bulleid, Rosemary A., Crabb, Simon J., Packham, Graham and Ganesan, A (2011) Enantioselective synthesis of tranylcypromine analogues as lysine demethylase (LSD1) inhibitors. Bioorganic & Medicinal Chemistry, 19 (12). pp. 3709-3716.

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Abstract

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.

Item Type: Article
Faculty \ School: Faculty of Science > School of Pharmacy
Depositing User: Users 2731 not found.
Date Deposited: 20 Oct 2011 10:36
Last Modified: 07 Nov 2019 16:30
URI: https://ueaeprints.uea.ac.uk/id/eprint/35102
DOI: 10.1016/j.bmc.2011.02.017

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