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.
Copyright © 2011. Published by Elsevier Ltd.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Antineoplastic Agents / chemical synthesis*
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Antineoplastic Agents / chemistry
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Antineoplastic Agents / pharmacology*
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Bromine / chemistry
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Cell Line, Tumor
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Cell Proliferation / drug effects
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Enzyme Inhibitors / chemical synthesis*
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Enzyme Inhibitors / chemistry
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Enzyme Inhibitors / pharmacology*
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Histone Demethylases / antagonists & inhibitors*
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Humans
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Inhibitory Concentration 50
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Molecular Structure
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Stereoisomerism
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Tranylcypromine / chemical synthesis*
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Tranylcypromine / chemistry
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Tranylcypromine / pharmacology*
Substances
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Antineoplastic Agents
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Enzyme Inhibitors
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Tranylcypromine
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Histone Demethylases
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Bromine