Cinnamic acid esters as potent inhibitors of fungal 17beta-hydroxysteroid dehydrogenase--a model enzyme of the short-chain dehydrogenase/reductase superfamily.

Bioorganic & Medicinal Chemistry Letters
Stanislav GobecTea Lanisnik Rizner

Abstract

We present the synthesis of a new family of nonsteroidal inhibitors of 17beta-hydroxysteroid dehydrogenase, designed from flavones and chalcones. Their inhibitory potential was screened on 17beta-hydroxysteroid dehydrogenase from the fungus Cochliobolus lunatus (17beta-HSDcl), a model enzyme of the short-chain dehydrogenase/reductase superfamily. In a series of cinnamates and related coumarin-3-carboxylates, a number of compounds proved to be potent inhibitors of both the oxidative and reductive reactions catalyzed by 17beta-HSDcl, with IC(50) values in the low micromolar range.

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Citations

Jun 2, 2005·Steroids·Katja KristanTea Lanisnik Rizner
Jun 7, 2005·Steroids·Katja KristanTea Lanisnik Rizner
Dec 13, 2005·Molecular and Cellular Endocrinology·Katja KristanStanislav Gobec
Dec 13, 2005·Molecular and Cellular Endocrinology·Petra BrozicStanislav Gobec
May 13, 2017·Biomolecules·Liudmila G KorkinaChiara de Luca
Mar 22, 2007·Journal of Enzyme Inhibition and Medicinal Chemistry·Matej ZivecStanislav Gobec
Jan 12, 2021·The Journal of Organic Chemistry·Tanmayee NandaPonneri Chandrababu Ravikumar
Jun 28, 2008·The Journal of Organic Chemistry·Christophe PardinJeffrey W Keillor
Nov 4, 2008·Chemico-biological Interactions·Katja KristanUros Urleb

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