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

Bioorganic and Medicinal Chemistry

Volumn 22, Issue 1, 2014, Pages 126-134

  Amato, Erica ^a   Bankemper, Tony ^a   Kidney, Rebecca ^a   Do, Thuy ^a   Onate, Alma ^a   Thowfeik, Fathima Shazna ^b   Merino, Edward J ^b   Paula, Stefan ^a   Ma, Lili ^a  

^a NORTHERN KENTUCKY UNIVERSITY   (United States)

^b UNIVERSITY OF CINCINNATI   (United States)

Author keywords

Aromatase inhibitors; Breast cancer; Estrogen; Fluorine; Functional groups; Isoflavanones

Indexed keywords

2 (4 PHENOXYPHENYL) 2,3 DIHYDRO 1H BENZO[F]CHROMAN 4 ONE; 3 (2 FLUOROPHENYL)CHROMAN 4 ONE; 3 (3 FLUOROPHENYL)CHROMAN 4 ONE; 3 (3,5 DIFLUOROPHENYL)CHROMAN 4 ONE; 3 (4 FLUOROPHENYL)CHROMAN 4 ONE; 3 [4 (TRIFLUOROMETHYL)PHENYL]CHROMAN 4 ONE; 4 CHROMANONE DERIVATIVE; 6 FLUORO 3 (PYRIDIN 3 YL)CHROMAN 4 ONE; 6 FLUORO 3 PHENYLCHROMAN 4 ONE; 6 METHOXY 3 (4 PHENOXYPHENYL)CHROMAN 4 ONE; 6 METHOXY 3 (PYRIDIN 3 YL)CHROMAN 4 ONE; 6,8 DIFLUORO 3 PHENYLCHROMAN 4 ONE; 8 FLUORO 3 (PYRIDIN 3 YL)CHROMAN 4 ONE; 8 FLUORO 3 PHENYLCHROMAN 4 ONE; AROMATASE INHIBITOR; ISOFLAVONE DERIVATIVE; LETROZOLE; UNCLASSIFIED DRUG;

ANNULATION REACTION; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; CANCER INHIBITION; CELL STRAIN MCF 7; DRUG STRUCTURE; DRUG SYNTHESIS; FLUORINATION; HUMAN; HUMAN CELL; HYDROGEN BOND; IC 50; MOLECULAR DOCKING; STRUCTURE ACTIVITY RELATION; SURFACE PROPERTY;

AIS; ARG 115; ARGININE 115; AROMATASE INHIBITORS; ASP 309; ASPARTIC ACID 309; BREAST CANCER; CYP19; CYTOCHROME P450 AROMATASE; ESTROGEN; FLUORINE; FUNCTIONAL GROUPS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HPLC; ILE 133; ISOFLAVANONES; ISOLEUCINE 133; LEU 477; LEUCINE 477; MASS SPECTROMETRY; MS; NMR; NON-STEROIDAL AROMATASE INHIBITORS; NSAIS; NUCLEAR MAGNETIC RESONANCE; PHE 221; PHENYLALANINE 221; SELECTIVE ESTROGEN RECEPTOR MODULATORS; SERMS; THR 310; THREONINE 310; TRP 224; TRYPTOPHAN 224; VAL 370; VALINE 370;

AROMATASE INHIBITORS; BREAST NEOPLASMS; CELL LINE, TUMOR; FEMALE; HUMANS; ISOFLAVONES;

EID: 84891494105     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2013.11.045     Document Type: Article

References (39)

1. American Cancer Society Cancer Facts & Figures 2013 2013 American Cancer Society Atlanta
2. J. Gray, N. Evans, B. Taylor, J. Rizzo, and M. Walker Int. J. Occ. Environ. Health 15 2009 43
3. Y. Muftuoglu, and G. Mustata Bioorg. Med. Chem. Lett. 20 2010 3050
4. M. Recanatini, A. Cavalli, and P. Valenti Med. Res. Rev. 22 2002 282
5. R.W. Brueggemeier, J.C. Hackett, and E.S. Diaz-Cruz Endocr. Rev. 26 2005 331
6. B.J.A. Furr Milestones in Drug Therapy. Aromatase Inhibitors 2nd ed. 2006 Birkhauser p 182
7. M.S. Christodoulou, N. Fokialakis, D. Passarella, A.N. Garcia-Argaez, O.M. Gia, I. Pongratz, L. Dalla Via, and S.A. Haroutounian Bioorg. Med. Chem. 21 2013 4120
8. A.R. Ibrahim, and Y.J. Abul-Hajj J. Steroid Biochem. Mol. Biol. 37 1990 257
9. R.W. Brueggemeier, J.A. Richards, S. Joomprabutra, A.S. Bhat, and J.L. Whetstone J. Steroid Biochem. Mol. Biol. 79 2001 75
10. K. Bonfield, E. Amato, T. Bankemper, H. Agard, J. Steller, J.M. Keeler, D. Roy, A. McCallum, S. Paula, and L. Ma Bioorg. Med. Chem. 20 2012 2603
11. S. Purser, P.R. Moore, S. Swallow, and V. Gouverneur Chem. Soc. Rev. 37 2008 320
12. P. Zhou, J. Zou, F. Tian, and Z. Shang J. Chem. Inf. Model. 49 2009 2344
13. N.A. Meanwell J. Med. Chem. 54 2011 2529
14. B.E. Smart J. Fluorine Chem. 109 2001 3
15. Ronald Eric Banks, B.E. Smart, and J.C. Tatlow Organofluorine Chemistry: Principles and Commercial Applications 1st ed. 1994 Springer p 669
16. R. Ahuja, and A.G. Samuelson Cryst. Eng. Commun. 5 2003 395
17. W.K. Hagmann J. Med. Chem. 51 2008 4359
18. A. Maiti, P.V.N. Reddy, M. Sturdy, L. Marler, S.D. Pegan, A.D. Mesecar, J.M. Pezzuto, and M. Cushman J. Med. Chem. 52 2009 1873
19. D.M. Stresser, S.D. Turner, J. McNamara, P. Stocker, V.P. Miller, C.L. Crespi, and C.J. Patten Anal. Biochem. 284 2000 427
20. Molinspiration, http://www.molinspiration.com/cgi-bin/properties (accessed 6-6-2013).
21. OSIRIS Property Explorer, http://www.organic-chemistry.org/prog/peo/ (accessed 6-6-2013).
22. T.R. Bell-Horwath, A.K. Vadukoot, F.S. Thowfeik, G. Li, M. Wunderlich, J.C. Mulloy, and E.J. Merino Bioorg. Med. Chem. Lett. 23 2013 2951
23. A.R. Jones, T.R. Bell-Horwath, G. Li, S.M. Rollmann, and E.J. Merino Chem. Res. Toxicol. 25 2012 2542
24. G. Li, T. Bell, and E.J. Merino ChemMedChem 6 2011 869
25. W.V. Welshons, and V. Craig Jordan Eur. J Cancer Clin. Oncol. 23 1987 1935
26. J.C. Le Bail, F. Varnat, J.C. Nicolas, and G. Habrioux Cancer Lett. 130 1998 209
27. I. Kijima, T. Itoh, and S. Chen J. Steroid Biochem. Mol. Biol. 97 2005 360
28. T.N. Mitropoulou, G.N. Tzanakakis, D. Kletsas, H.P. Kalofonos, and N.K. Karamanos Int. J. Cancer 104 2003 155
29. D. Ghosh, J. Griswold, M. Erman, and W. Pangborn Nature 457 2009 219
30. E.H. Kerns, and L. Di Drug-like Properties: Concepts, Structure Design and Methods. from ADME to Toxicity Optimization 2nd ed. 2008 Elsevier Inc. p 552
31. M. Namazian, and M.L. Coote J. Fluorine Chem. 130 2009 621
32. P. Rowland, F.E. Blaney, M.G. Smyth, J.J. Jones, V.R. Leydon, A.K. Oxbrow, C.J. Lewis, M.G. Tennant, S. Modi, D.S. Eggleston, R.J. Chenery, and A.M. Bridges J. Biol. Chem. 281 2006 7614
33. P.A. Williams, J. Cosme, D.M. Vinković, A. Ward, H.C. Angove, P.J. Day, C. Vonrhein, I.J. Tickle, and H. Jhoti Science 305 2004 683
34. M. Imhof, and S. Molzer Toxicol. In Vitro 22 2008 1452
35. F. Bellina, T. Masini, and R. Rossi Eur. J. Org. Chem. 2010 2010 1339
36. M. Lessi, T. Masini, L. Nucara, F. Bellina, and R. Rossi Adv. Synth. Catal. 353 2011 501
37. S. Paula, and W.J. Ball Jr. Proteins 56 2004 595
38. G. Jones, P. Willett, and R.C. Glen J. Mol. Biol. 245 1995 43
39. G. Jones, P. Willett, R.C. Glen, A.R. Leach, and R. Taylor J. Mol. Biol. 267 1997 727