TY - JOUR
T1 - Enantioselective synthesis of tranylcypromine analogues as lysine demethylase (LSD1) inhibitors
AU - Benelkebir, Hanae
AU - Hodgkinson, Christopher
AU - Duriez, Patrick J.
AU - Hayden, Annette L.
AU - Bulleid, Rosemary A.
AU - Crabb, Simon J.
AU - Packham, Graham
AU - Ganesan, A
PY - 2011/6/15
Y1 - 2011/6/15
N2 - 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.
AB - 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.
U2 - 10.1016/j.bmc.2011.02.017
DO - 10.1016/j.bmc.2011.02.017
M3 - Article
VL - 19
SP - 3709
EP - 3716
JO - Bioorganic & Medicinal Chemistry
JF - Bioorganic & Medicinal Chemistry
SN - 0968-0896
IS - 12
ER -
