2. Academic Validation
  3. Enantioselective synthesis of tranylcypromine analogues as lysine demethylase (LSD1) inhibitors

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

  • Bioorg Med Chem. 2011 Jun 15;19(12):3709-16. doi: 10.1016/j.bmc.2011.02.017.
Hanae Benelkebir 1,  Christopher Hodgkinson,  Patrick J Duriez,  Annette L Hayden,  Rosemary A Bulleid,  Simon J Crabb,  Graham Packham,  A Ganesan
Affiliations

Affiliation

  • 1 School of Chemistry, University of Southampton, Southampton SO17 1BJ, United Kingdom.
PMID: 21382717 DOI: 10.1016/j.bmc.2011.02.017
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.

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