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ID: ALA4052631

Journal: Eur J Med Chem

Title: Synthesis of selective 11β-HSD1 inhibitors based on dammarane scaffold.

Authors: Shao LD, Bao Y, Shen Y, Su J, Leng Y, Zhao QS.

Abstract: Inspired by natural 11β-HSD1 inhibitors hupehenols A - E, a ring-focused strategy was applied for the synthesis of 35 structurally diverse dammarane-type derivatives. These derivatives were effectively prepared from protopanaxadiol based on the modification of rings A and D. Among these compounds, ten were identified as selective 11β-HSD1 inhibitors (IC50 range: 101-1047 nM, SI range: 8-169) which exhibited inhibitory activities against human or mouse 11β-HSD1. Otherwise, we found 23a could selectively inhibit both human and mouse 11β-HSD1 with IC50 value of 994 and 213 nM (SI > 10 and > 47), respectively. Additionally, the molecular modelling results of 23a docking into the human and mouse 11β-HSD1 were in good agreement with the results from the enzyme inhibitory experiment. Moreover, valuable structural-activity relationship (SAR) information of dammarane-type 11β-HSD1 inhibitor was summarized.

CiteXplore: 28458137

DOI: 10.1016/j.ejmech.2017.04.059