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Literature DB >> 24345481

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

Erica Amato¹, Tony Bankemper¹, Rebecca Kidney¹, Thuy Do¹, Alma Onate¹, Fathima Shazna Thowfeik², Edward J Merino², Stefan Paula¹, Lili Ma³.

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.

Entities: CellLine Chemical Disease Gene Species

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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Year: 2013 PMID： 24345481 PMCID： PMC3933948 DOI： 10.1016/j.bmc.2013.11.045

Source DB: PubMed Journal: Bioorg Med Chem ISSN： 0968-0896 Impact factor: 3.641

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References

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