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Issue 4, 2013
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Investigation of a tetrahydroisoquinoline scaffold as dual-action steroid sulfatase inhibitors generated by parallel solid-phase synthesis

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Abstract

Various derivatives of the tetrahydroisoquinoline core were designed as non-steroidal dual-action inhibitors of steroid sulfatase (STS). Sulfamate derivatives and their corresponding phenol derivatives were both synthesized by parallel solid-phase chemistry. The sulfamate compounds were tested for their ability to inhibit STS activity, whereas the phenol compounds were tested for their ability or non-ability to induce the proliferation of estrogen-dependent MCF-7 and Saos-2 cells. Interestingly, many sulfamate derivatives showed good inhibitory activity toward the enzyme (80–90% of inhibition at 0.1 μM), whereas four phenol derivatives did not present unwanted estrogenic activity on MCF-7 cells but induced a proliferation of Saos-2 cells, thus suggesting a selective-estrogen receptor modulator potential.

Graphical abstract: Investigation of a tetrahydroisoquinoline scaffold as dual-action steroid sulfatase inhibitors generated by parallel solid-phase synthesis

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Supplementary files

Article information


Submitted
28 Aug 2012
Accepted
04 Feb 2013
First published
05 Feb 2013

Med. Chem. Commun., 2013,4, 681-692
Article type
Concise Article

Investigation of a tetrahydroisoquinoline scaffold as dual-action steroid sulfatase inhibitors generated by parallel solid-phase synthesis

É. Ouellet, R. Maltais, C. Ouellet and D. Poirier, Med. Chem. Commun., 2013, 4, 681
DOI: 10.1039/C3MD20354A

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