Synthesis and structure–activity relationships of 2- and/or 4-halogenated 13β- and 13α-estrone derivatives as enzyme inhibitors of estrogen biosynthesis

Ildikó Bacsa, Bianka Edina Herman, Rebeka Jójárt, Kevin Stefán Herman, J. Wölfling, G. Schneider, Mónika Varga, C. Tömböly, Tea Lanišnik Rižner, Mihály Szécsi, E. Mernyák

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Ring A halogenated 13α-, 13β-, and 17-deoxy-13α-estrone derivatives were synthesised with N-halosuccinimides as electrophile triggers. Substitutions occurred at positions C-2 and/or C-4. The potential inhibitory action of the halogenated estrones on human aromatase, steroid sulfatase, or 17β-hydroxysteroid dehydrogenase 1 activity was investigated via in vitro radiosubstrate incubation. Potent submicromolar or low micromolar inhibitors were identified with occasional dual or multiple inhibitory properties. Valuable structure–activity relationships were established from the comparison of the inhibitory data obtained. Kinetic experiments performed with selected compounds revealed competitive reversible inhibition mechanisms against 17β-hydroxysteroid dehydrogenase 1 and competitive irreversible manner in the inhibition of the steroid sulfatase enzyme.

Original languageEnglish
Pages (from-to)1271-1282
Number of pages12
JournalJournal of Enzyme Inhibition and Medicinal Chemistry
Issue number1
Publication statusPublished - Jan 1 2018



  • 17β-HSD1
  • aromatase
  • Estrone
  • halogenations
  • STS

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery

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