New aromatase inhibitors. Synthesis and inhibitory activity of pyridinyl-substituted flavanone derivatives.
Two (E)-pyridinyl-substituted flavanone derivatives were synthesized and UV irradiation of these compounds afforded a Z-enriched mixture. These products were tested for their ability to inhibit the cytochrome P450 aromatase. It was observed that the introduction of a pyridinylmethylene group at carbon 3 on flavanone nucleus led to a significant increase of aromatase inhibitory effect. Moreover, configuration had a substantial influence on the aromatase inhibitory activity since (E)-isomers were found to be more active than (Z)-isomers.
Pouget
Christelle
C
UPRES EA 1085, Biomolécules et cibles cellulaires tumorales, Faculté de Pharmacie, 2 rue du Docteur Marcland, 87025 Limoges cedex, France.
Fagnere
Catherine
C
Basly
Jean-Philippe
JP
Habrioux
Gerard
G
Chulia
Albert-José
AJ
D000735:Androstenedione / Q000737:chemistry / Q000378:metabolism; D047072:Aromatase Inhibitors; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D044950:Flavanones; D005419:Flavonoids / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D006801:Humans; D066298:In Vitro Techniques; D008297:Male; D008861:Microsomes / Q000187:drug effects / Q000201:enzymology; D008958:Models, Molecular; D010920:Placenta / Q000378:metabolism; D011725:Pyridines / Q000737:chemistry*; D013329:Structure-Activity Relationship
D047072:Aromatase Inhibitors; D004791:Enzyme Inhibitors; D044950:Flavanones; D005419:Flavonoids; D011725:Pyridines; D000735:Androstenedione; C023666:pyridine; C028610:flavanone