Synthesis and structure-activity relationships for 1-(4-(piperidin-1- ylsulfonyl)phenyl)pyrrolidin-2-ones as novel non-carboxylate inhibitors of the aldo-keto reductase enzyme AKR1C3

European Journal of Medicinal Chemistry

Volumn 62, Issue , 2013, Pages 738-744

  Heinrich, Daniel M ^a   Flanagan, Jack U ^a,b   Jamieson, Stephen M F ^a,b   Silva, Shevan ^a   Rigoreau, Laurent J M ^c   Trivier, Elisabeth ^c   Raynham, Tony ^c   Turnbull, Andrew P ^d   Denny, William A ^a,b  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

^b UNIVERSITY OF AUCKLAND   (New Zealand)

^c UNIVERSITY COLLEGE LONDON   (United Kingdom)

^d UNIVERSITY OF LONDON   (United Kingdom)

Author keywords

Aldo keto reductase; Computer aided drug design; Crystal structure; Inhibitor

Indexed keywords

1 [3 (2 METHYLPIPERIDIN 1 YLSULFONYL)PHENYL]PYRROLIDIN 2 ONE; 1 [4 (2 METHYLPIPERIDIN 1 YLSULFONYL)PHENYL]AZETIDIN 2 ONE; 1 [4 (2 METHYLPIPERIDIN 1 YLSULFONYL)PHENYL]PIPERIDIN 2 ONE; 1 [4 (2 METHYLPIPERIDIN 1 YLSULFONYL)PHENYL]PYRROLIDINE 2,5 DIONE; 1 [4 (PIPERIDIN 1 YLSULFONYL)PHENYL]PYRROLIDIN 2 ONE; OXIDOREDUCTASE; OXIDOREDUCTASE INHIBITOR; PROTEIN AKR1C3; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; COMPETITIVE INHIBITION; CORRELATION ANALYSIS; CRYSTAL STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY;

3-HYDROXYSTEROID DEHYDROGENASES; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; HCT116 CELLS; HUMANS; HYDROXYPROSTAGLANDIN DEHYDROGENASES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PYRROLIDINONES; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES;

EID: 84876000571     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.01.047     Document Type: Article

References (18)

1. M.C. Byrns, Y. Jin, and T.M. Penning J. Steroid. Biochem. Mol. Biol. 125 2011 95 104
2. J.C. Desmond, J.C. Mountford, M.T. Drayson, E.A. Walker, M. Hewison, J.P. Ride, Q.T. Luong, R.E. Hayden, E.F. Vanin, and C.M. Bunce Cancer Res. 63 2003 505 512
3. T.M. Penning, M.E. Burczynski, L.M. Jez, H.-K. Lin, H. Ma, M. Moore, K. Ratnam, and N. Palackal Mol. Cell. Endocrinol. 171 2001 137 149
4. S.M.F. Jamieson, D.G. Brooke, D. Heinrich, G.J. Atwell, S. Silva, E.J. Hamilton, A.P. Turnbull, L.J.M. Rigoreau, E. Trivier, C. Soudy, S.S. Samlal, P.J. Owen, E. Schroeder, T. Raynham, J.U. Flanagan, and W.A. Denny J. Med. Chem. 55 2012 7746 7758
5. A.O. Adeniji, B.M. Twenter, M.C. Byrns, Y. Jin, M. Chen, J.D. Winkler, and T.M. Penning J. Med. Chem. 55 2012 2311 2323
6. J.M. Jez, M.J. Bennett, B.P. Schlegel, M. Lewis, and T.M. Penning Biochem. J. 326 1997 625 636
7. A.L. Lovering, J.P. Ride, C.M. Bunce, J.C. Desmond, S.M. Cummings, and S.A. White Cancer Res. 64 2004 1802 1810
8. M.C. Byrns, and T.M. Penning Chem. Biol. Interact. 178 2009 221 227
9. D.R. Bauman, S.L. Rudnick, L.M. Szewczuk, Y. Jin, S. Gopishetty, and T.M. Penning Mol. Pharmacol. 67 2005 60 68
10. V.J. Jackson, Y. Yosaamadja, J.U. Flanagan, and C.J. Squire Acta Crystallogr. F68 2012 409 413
11. J.U. Flanagan, Y. Yossatmadja, R.M. Teague, M.Z.L. Chai, A.P. Turnbull, C.J. Squire, PLoS One 7 (8) e43965, doi:10.1371/journal.pone.0043965.
12. T. Ogihara, I. Tamai, and A. Tsuji A. J. Pharm. Sci. 88 1999 1217 1221
13. D.J. Yee, V. Balsanek, and D. Sames J. Am. Chem. Soc. 126 2004 2282 2283
14. C.P. Guise, M.R. Abbattista, R.S. Singleton, S.D. Holford, J. Connolly, G.U. Dachs, S.B. Fox, R. Pollock, J. Harvey, P. Guilford, F. Donate, W.R. Wilson, and A.V. Patterson Cancer Res. 70 2010 1573 1584
15. A. Klapars, X. Huang, and S.L. Buchwald A general and efficient copper catalyst for the amidation of aryl halides J. Am. Chem. Soc. 124 2004 7421 7428
16. J. Yin, and S.L. Buchwald Org. Lett. 2 2000 1101 1104
17. J.J. Cui. WO 2004/76412 A2, published 10th Sept 2004.
18. T.D. Warner, F. Giuliano, L. Vojnovic, A. Bukasa, J.A. Mitchell, and J.R. Vane Proc. Natl. Acad. Sci. U. S. A. 96 1999 7563 7568