PuSH - Publikationsserver des Helmholtz Zentrums München: Structural optimization of 2,5-tiophene amides as highly potent and selective 17<em>β</em>-hydroxysteroid dehydrogenase type 2 inhibitors for the treatment of osteoporosis.

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Marchais-Oberwinkler, S.* ; Xu, K.* ; Wetzel, M.* ; Perspicace, E.* ; Negri, M.* ; Odermatt, A.* ; Möller, G. ; Adamski, J. ; Hartmann, R.W.*

Structural optimization of 2,5-tiophene amides as highly potent and selective 17β-hydroxysteroid dehydrogenase type 2 inhibitors for the treatment of osteoporosis.

J. Med. Chem. 56, 167-181 (2013)

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Open Access Green möglich sobald Postprint bei der ZB eingereicht worden ist.

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Inhibition of 17β-HSD2 is an attractive mechanism for the treatment of osteoporosis. We report here the optimization of human 17β-HSD2 inhibitors in the 2,5-thiophene amide class by varying the size of the linker (n equals 0 and 2) between the amide moiety and the phenyl group. While none of the phenethylamides (n = 2) were active, most of the anilides (n = 0) turned out to moderately or strongly inhibit 17β-HSD2. The four most active compounds showed an IC(50) of around 60 nM and a very good selectivity toward 17β-HSD1, 17β-HSD4, 17β-HSD5, 11β-HSD1, 11β-HSD2 and the estrogen receptors α and β. The investigated compounds inhibited monkey 17β-HSD2 moderately, and one of them showed good inhibitory activity on mouse 17β-HSD2. SAR studies allowed a first characterization of the human 17β-HSD2 active site, which is predicted to be considerably larger than that of 17β-HSD1.

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