Synthesis of enterolactone and enterodiol precursors as potential inhibitors of human estrogen synthetase (aromatase).
A series of variably substituted derivatives of lignan lactones and diols were prepared using tandem conjugate addition reaction as a key step. These theoretical precursors of the mammalian lignans enterolactone 1 and enterodiol 3 are moderate or weak inhibitors of human aromatase activity.
Organic Chemistry Laboratory, Department of Chemistry, P.O. Box 55 (A.I. Virtasen aukio 1), FIN-00014 University of Helsinki, Helsinki, Finland. taru.makela@helsinki.fi
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D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D047072:Aromatase Inhibitors; D002396:Catechols / Q000138:chemical synthesis* / Q000494:pharmacology*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*; D006801:Humans; D017705:Lignans / Q000737:chemistry; D010636:Phenols / Q000138:chemical synthesis* / Q000494:pharmacology*
C413893:3'-demethoxysecoisolariciresinol; C413892:3-demethoxy-3'-O-demethylmatairesinol; D047072:Aromatase Inhibitors; D002396:Catechols; D004791:Enzyme Inhibitors; D017705:Lignans; D010636:Phenols; C029498:2,3-bis(3'-hydroxybenzyl)butane-1,4-diol; D015107:4-Butyrolactone; C029497:2,3-bis(3'-hydroxybenzyl)butyrolactone