Regioselective synthesis and estrogenicity of (±)-8-alkyl-5,7-dihydroxy-4-(4-hydroxyphenyl)-3,4-dihydrocoumarins

Nine new (±)-8-alkyl-5,7-dihydroxy-4-(4-hydroxyphenyl)-3,4-dihydrocoumarins have been synthesized from 2,4,6-trimethoxybenzaldehyde via a short, efficient, and regioselective pathway, together with the unsubstituted analogue (±)-5,7-dihydroxy-4-(4-hydroxyphenyl)-3,4-dihydrocoumarin. The compounds we...

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Veröffentlicht in:	European journal of medicinal chemistry 2005-10, Vol.40 (10), p.1042-1051
Hauptverfasser:	Roelens, Frederik, Huvaere, Kevin, Dhooge, Willem, Van Cleemput, Marjan, Comhaire, Frank, De Keukeleire, Denis
Format:	Artikel
Sprache:	eng
Schlagworte:	Biological and medical sciences Coumarins - chemical synthesis Coumarins - chemistry Coumarins - pharmacology Estrogens - pharmacology Hormones. Endocrine system Medical sciences Molecular Structure Neoflavanones Pharmacology. Drug treatments Phytoestrogens Recombinant yeast estrogen screen Saccharomyces cerevisiae - drug effects Structure-Activity Relationship
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Beschreibung
Zusammenfassung:	Nine new (±)-8-alkyl-5,7-dihydroxy-4-(4-hydroxyphenyl)-3,4-dihydrocoumarins have been synthesized from 2,4,6-trimethoxybenzaldehyde via a short, efficient, and regioselective pathway, together with the unsubstituted analogue (±)-5,7-dihydroxy-4-(4-hydroxyphenyl)-3,4-dihydrocoumarin. The compounds were tested for estrogenic activity using a yeast-based estrogen screen. Weak estrogenicity was determined for seven members of the series.
ISSN:	0223-5234 1768-3254
DOI:	10.1016/j.ejmech.2005.04.010