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Structure Confirmation and Evaluation of a Nonsteroidal Inhibitor of 17β-Hydroxysteroid Dehydrogenase Type 10

Endocrinology and Nephrology Unit, Laboratory of Medicinal Chemistry, CHU de Québec—Research Center, Québec, QC G1V 4G2, Canada
Department of Molecular Medicine, Faculty of Medicine, Université Laval, Québec, QC G1V 4G2, Canada
Author to whom correspondence should be addressed.
Magnetochemistry 2018, 4(3), 32;
Received: 30 April 2018 / Revised: 13 July 2018 / Accepted: 16 July 2018 / Published: 23 July 2018
PDF [1580 KB, uploaded 23 July 2018]


17β-Hydroxysteroid dehydrogenase type 10 (17β-HSD10) is a steroidogenesis enzyme known for its potential role in Alzheimer’s disease. For comparison purposes between steroidal and nonsteroidal 17β-HSD10 inhibitors 1 and 2, respectively, we attempted the chemical synthesis of benzothiazole phosphonate derivative 2. Instead of a one-pot synthesis, we report a two-step synthesis with characterization of both imine intermediate 5 and final compound 2. Furthermore, complete assignation of 1H and 13C nuclear magnetic resonance (NMR) signals of 2 is provided, as we observed a divergence of NMR data with those published previously. Finally, biological assays showed that 1 and 2 inhibited the oxidation of estradiol (E2) into estrone (E1) by the 17β-HSD10 recombinant protein. However, in human embryonic kidney (HEK)-293 intact cells transfected with 17β-HSD10, only the steroidal inhibitor 1 induced a dose-dependent inhibition of E2 to E1 transformation. View Full-Text
Keywords: NMR; chemical synthesis; enzyme inhibitor; 17β-HSD10; Alzheimer’s NMR; chemical synthesis; enzyme inhibitor; 17β-HSD10; Alzheimer’s

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Boutin, S.; Poirier, D. Structure Confirmation and Evaluation of a Nonsteroidal Inhibitor of 17β-Hydroxysteroid Dehydrogenase Type 10. Magnetochemistry 2018, 4, 32.

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