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Flavonoids and cinnamic acid esters as inhibitors of fungal 17ß-hydroxysteroid dehydrogenase : a synthesis, QSAR and modelling study
Sova, Matej, 1979- ...
The 17ß-hydroxysteroid dehydrogenases (17ß-HSDs) modulate the biological potency of estrogens and androgens by interconversion of inactive 17-keto-steroids and their active 17ß-hydroxy- counterparts. ...We have shown previously that flavonoids are potentially useful lead compounds for developing inhibitors of 17ß-HSDs. In this paper, we describe the synthesis and biochemical evaluation of structurally analogous inhibitors, the traps-cinnamic acid esters and related compounds. Additionally, quantitative structure-activity relationship (QSAR) and modelling studies were performed torationalize the results and to suggest further optimization. The results stress the importance of a hydrogen bond with Asn154 and hydrophobic interactions with the aromatic side chain of Tyr212 for optimal molecular recognition.
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