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
Uncontrolled Keywords:	sdg 3 - good health and well-being ,/dk/atira/pure/sustainabledevelopmentgoals/good_health_and_well_being
Faculty \ School:	Faculty of Science > School of Pharmacy (former - to 2024)
UEA Research Groups:	Faculty of Science > Research Groups > Medicinal Chemistry (former - to 2017) Faculty of Science > Research Groups > Chemical Biology and Medicinal Chemistry (former - to 2021)
Depositing User:	Users 2731 not found.
Date Deposited:	20 Oct 2011 10:36
Last Modified:	28 Mar 2025 02:44
URI:	https://ueaeprints.uea.ac.uk/id/eprint/35102
DOI:	10.1016/j.bmc.2011.02.017

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