2. Academic Validation
  3. Investigation of fluorinated and bifunctionalized 3-phenylchroman-4-one (isoflavanone) aromatase inhibitors

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

  • Bioorg Med Chem. 2014 Jan 1;22(1):126-34. doi: 10.1016/j.bmc.2013.11.045.
Erica Amato 1,  Tony Bankemper 1,  Rebecca Kidney 1,  Thuy Do 1,  Alma Onate 1,  Fathima Shazna Thowfeik 2,  Edward J Merino 2,  Stefan Paula 1,  Lili Ma 3
Affiliations

Affiliations

  • 1 Department of Chemistry, Northern Kentucky University, Nunn Drive, Highland Heights, KY 41099, United States.
  • 2 Department of Chemistry, University of Cincinnati, Cincinnati, OH 45221, United States.
  • 3 Department of Chemistry, Northern Kentucky University, Nunn Drive, Highland Heights, KY 41099, United States. Electronic address: mal1@nku.edu.
PMID: 24345481 DOI: 10.1016/j.bmc.2013.11.045
Abstract

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 2.5 μM and 0.8 μM. Therefore, these compounds have great potential for the development of pharmaceutical agents against breast Cancer.

Keywords

AIs; Arg 115; Aromatase inhibitors; Asp 309; Breast cancer; CYP19; Estrogen; Fluorine; Functional groups; HPLC; Ile 133; Isoflavanones; Leu 477; MS; NMR; NSAIs; Phe 221; SERMs; Thr 310; Trp 224; Val 370; arginine 115; aromatase inhibitors; aspartic acid 309; cytochrome P450 aromatase; high performance liquid chromatography; isoleucine 133; leucine 477; mass spectrometry; non-steroidal aromatase inhibitors; nuclear magnetic resonance; phenylalanine 221; selective estrogen receptor modulators; threonine 310; tryptophan 224; valine 370.

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