@article{
 title = {Development of a new class of aromatase inhibitors: Design, synthesis and inhibitory activity of 3-phenylchroman-4-one (isoflavanone) derivatives.},
 type = {article},
 year = {2012},
 identifiers = {[object Object]},
 keywords = {Antitumor agents,Cyclization (microwave-assisted, gold-catalyzed,Drug targets,Human,Hydrogen bond,Mammary gland,Molecular association,Molecular modeling,SAR,Structure-activity relationship (phenylchromanones,aromatase,breast,cancer,inhibitors,phenylchromanone,phenylchromanones as aromatase inhibitors),prepn},
 pages = {2603-2613},
 volume = {20},
 city = {Department of Chemistry, Northern Kentucky University, Highland Heights, KY, USA.},
 id = {7956160d-7679-3fb7-b463-1413dac84e14},
 created = {2016-06-29T14:03:59.000Z},
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 group_id = {29d6b3c5-c367-360f-ab93-7112ec5bf183},
 last_modified = {2017-03-14T11:59:07.894Z},
 read = {false},
 starred = {false},
 authored = {false},
 confirmed = {true},
 hidden = {false},
 citation_key = {Bonfield2012a},
 source_type = {JOUR},
 notes = {Copyright (C) 2012 American Chemical Society (ACS). All Rights Reserved.; Section Code: 1-3; CA Section Cross-references: 26; CODEN: BMECEP; CAS Registry Numbers: 14875-96-8 (Heme) Role: BSU (Biological study, unclassified), BIOL (Biological study) (phenylchromanones as aromatase inhibitors); 506-65-0 (Gold cyanide) Role: CAT (Catalyst use), USES (Uses) (phenylchromanones as aromatase inhibitors); 5128-69-8P; 42327-60-6P; 42327-62-8P; 42327-64-0P; 42383-45-9P; 124093-45-4P; 140870-50-4P; 140870-51-5P; 934550-24-0P; 1143863-71-1P; 1370604-83-3P; 1370604-84-4P; 1370604-85-5P; 1370604-86-6P; 1370604-87-7P; 1370604-88-8P; 1370604-90-2P; 1370604-91-3P; 1370604-92-4P; 1370604-93-5P; 1370604-94-6P; 1370604-95-7P Role: PAC (Pharmacological activity), SPN (Synthetic preparation), THU (Therapeutic use), BIOL (Biological study), PREP (Preparation), USES (Uses) (phenylchromanones as aromatase inhibitors); 4737-27-3 Role: PAC (Pharmacological activity), THU (Therapeutic use), BIOL (Biological study), USES (Uses) (phenylchromanones as aromatase inhibitors); 90-02-8; 148-53-8; 347-54-6; 536-74-3; 613-84-3; 635-93-8; 672-13-9; 673-22-3; 698-27-1; 708-06-5; 766-82-5; 766-97-2; 767-91-9; 768-60-5; 768-70-7; 824-42-0; 1761-61-1; 2510-23-8; 2725-53-3; 4200-06-0; 29079-00-3; 32870-98-7; 67237-53-0; 171290-52-1 Role: RCT (Reactant), RACT (Reactant or reagent) (phenylchromanones as aromatase inhibitors)},
 private_publication = {false},
 abstract = {Aromatase (CYP19) catalyzes the aromatization reaction of androgen substrates to estrogens, the last and rate-limiting step in estrogen biosynthesis. Inhibition of aromatase is a new and promising approach to treat hormone-dependent breast cancer. We present here the design and development of isoflavanone derivs. as potential aromatase inhibitors. Structural modifications were performed on the A and B rings of isoflavanones via microwave-assisted, gold-catalyzed annulation reactions of hydroxyaldehydes and alkynes. The in vitro aromatase inhibition of these compds. was detd. by fluorescence-based assays utilizing recombinant human aromatase (baculovirus/insect cell-expressed). The compds. 3-(4-phenoxyphenyl)chroman-4-one (1h), 6-methoxy-3-phenylchroman-4-one (2a) and 3-(pyridin-3-yl)chroman-4-one (3b) exhibited potent inhibitory effects against aromatase with IC50 values of 2.4 μM, 0.26 μM and 5.8 μM, resp. Docking simulations were employed to investigate crucial enzyme/inhibitor interactions such as hydrophobic interactions, hydrogen bonding and heme iron coordination. This report provides useful information on aromatase inhibition and serves as a starting point for the development of new flavonoid aromatase inhibitors. [on SciFinder(R)]},
 bibtype = {article},
 author = {Bonfield, Kevin and Amato, Erica and Bankemper, Tony and Agard, Hannah and Steller, Jeffrey and Keeler, James M and Roy, David and McCallum, Adam and Paula, Stefan and Ma, Lili},
 journal = {Section Title: Pharmacology},
 number = {8}
}

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