Investigation of fluorinated and bifunctionalized 3-phenylchroman-4-one (isoflavanone) aromatase inhibitors

Fluorinated isoflavanones and bifunctionalized isoflavanones were synthesized through a one-step gold(I)-catalyzed annulation reaction. These compounds were evaluated for their in vitro inhibitory activities against aromatase in a fluorescence-based enzymatic assay. Selected compounds were tested fo...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2014-01, Vol.22 (1), p.126-134
Main Authors: Amato, Erica, Bankemper, Tony, Kidney, Rebecca, Do, Thuy, Onate, Alma, Thowfeik, Fathima Shazna, Merino, Edward J., Paula, Stefan, Ma, Lili
Format: Article
Language:English
Subjects:
Aromatase inhibitors
Aromatase Inhibitors - pharmacology
Breast cancer
Breast Neoplasms - drug therapy
Breast Neoplasms - metabolism
Cell Line, Tumor
Estrogen
Female
Fluorine
Functional groups
Humans
Isoflavanones
Isoflavones - pharmacology
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Summary:Fluorinated isoflavanones and bifunctionalized isoflavanones were synthesized through a one-step gold(I)-catalyzed annulation reaction. These compounds were evaluated for their in vitro inhibitory activities against aromatase in a fluorescence-based enzymatic assay. Selected compounds were tested for their anti-proliferative effects on human breast cancer cell line MCF-7. Compounds 6-methoxy-3-(pyridin-3-yl)chroman-4-one (3c) and 6-fluoro-3-(pyridin-3-yl)chroman-4-one (3e) were identified as the most potent aromatase inhibitors with IC50 values of 2.5μM and 0.8μM. Therefore, these compounds have great potential for the development of pharmaceutical agents against breast cancer.
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2013.11.045