Structure-activity study in the class of 6-(3'-hydroxyphenyl)naphthalenes leading to an optimization of a pharmacophore model for 17beta-hydroxysteroid dehydrogenase type 1 (17beta-HSD1) inhibitors

Sandrine Marchais-Oberwinkler, Martin Frotscher, Erika Ziegler, Ruth Werth, Patricia Kruchten, Josef Messinger, Hubert Thole, Rolf W Hartmann
Molecular and cellular endocrinology · 2009 · doi:10.1016/j.mce.2008.09.024 · PMID:18950679
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This study developed a pharmacophore model and designed a new class of non-steroidal 17beta-HSD1 inhibitors, optimizing a 6-(3'-hydroxyphenyl)-2-naphthol scaffold to find compound 18 with nanomolar potency and good selectivity.

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I can’t access the paper content because the provided text is blocked by an anti-bot “Anubis” challenge page, so I don’t have the study’s methods, results, or stated limitations to summarize. The title indicates a structure-activity relationship effort to optimize a pharmacophore model and improve 17β-hydroxysteroid dehydrogenase type 1 (17β-HSD1) inhibitor candidates, but no specific findings are available here. The paper does not explicitly discuss endometriosis or adenomyosis; it was included in the corpus via a keyword match in the upstream search index.

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Abstract

17beta-Hydroxysteroid dehydrogenase type 1 (17beta-HSD1) catalyzes the transformation of estrone (E1) into the most potent estrogen, estradiol (E2), which stimulates cell proliferation and decreases apoptosis. 17beta-HSD1 is often strongly overexpressed in estrogen-dependent diseases (like breast cancer and endometriosis). Thus, this over expressed enzyme is a promising novel target for the development of selective inhibitors, which could be used as drugs for the treatment of these diseases. Using a structure- and ligand-based approach, a pharmacophore model was proposed and a new class of non-steroidal inhibitors of 17beta-HSD1 was designed. Enzyme inhibition was evaluated in vitro using the human enzyme. After identification of the 6-(3'-hydroxyphenyl)-2-naphthol scaffold 1, the potency of this class of inhibitors was further improved by substitution of the 1-position of the naphthalene ring by a phenyl group (compound 18, IC(50)=20nM). Compound 18 also showed a good selectivity toward 17beta-HSD2 and the estrogen receptors alpha and beta.
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Condition tags

endometriosis

MeSH descriptors

Enzyme Inhibitors Enzyme Inhibitors Estradiol Dehydrogenases Models, Molecular Naphthalenes Naphthalenes Enzyme Inhibitors Estradiol Dehydrogenases Humans Inhibitory Concentration 50 Naphthalenes Structure-Activity Relationship

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europepmc
last seen: 2026-06-11T06:19:48.454388+00:00
pubmed
last seen: 2026-05-13T22:14:24.299271+00:00
unpaywall
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Courtesy of the U.S. National Library of Medicine