Structure-activity relationships (SAR) and structure-kinetic relationships (SKR) of bicyclic heteroaromatic acetic acids as potent CRTh2 antagonists III: The role of a hydrogen-bond acceptor in long receptor residence times

Bioorganic and Medicinal Chemistry Letters

Volumn 24, Issue 21, 2014, Pages 5127-5133

  Alonso, Juan Antonio ^a   Andrés, Miriam ^a   Bravo, Mónica ^a   Buil, Maria Antonia ^a   Calbet, Marta ^a   Castro, Jordi ^a   Eastwood, Paul R ^a   Esteve, Cristina ^a   Ferrer, Manel ^a   Forns, Pilar ^a   Gómez, Elena ^a   González, Jacob ^a   Lozoya, Estrella ^a   Mir, Marta ^a   Moreno, Imma ^a   Petit, Silvia ^a   Roberts, Richard S ^a   Sevilla, Sara ^a   Vidal, Bernat ^a   Vidal, Laura ^a   Vilaseca, Pere ^a   more..

^a Almirall R and D Centre ^*  (Spain)

Author keywords

CRTh2 antagonist; Hydrogen bond acceptor; Long residence time; Structure activity relationship (SAR); Structure kinetic relationship (SKR)

Indexed keywords

ACETIC ACID DERIVATIVE; CHEMOKINE RECEPTOR ANTAGONIST; HYDROGEN; BICYCLO COMPOUND; IMMUNOGLOBULIN RECEPTOR; PROSTAGLANDIN D2 RECEPTOR; PROSTAGLANDIN RECEPTOR;

ALDOL REACTION; ALKYLATION; ARTICLE; BROMINATION; COMPUTER MODEL; CONTROLLED STUDY; DISSOCIATION; DRUG CONFORMATION; DRUG HALF LIFE; DRUG POTENCY; HUMAN; HUMAN CELL; HYDROGEN BOND; IC50; LIPOPHILICITY; PHARMACOPHORE; PHYSICAL CHEMISTRY; PLASMA PROTEIN BINDING; STRUCTURE ACTIVITY RELATION; ANTAGONISTS AND INHIBITORS; CHEMICAL MODEL; CHEMISTRY; HALF LIFE TIME; METABOLISM; SYNTHESIS;

ACETATES; BICYCLO COMPOUNDS; HALF-LIFE; HUMANS; HYDROGEN BONDING; MODELS, CHEMICAL; RECEPTORS, IMMUNOLOGIC; RECEPTORS, PROSTAGLANDIN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84907990927     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2014.08.028     Document Type: Article

References (44)

1. K. Nagata, K. Tanaka, K. Ogawa, K. Kemmotsu, T. Imai, O. Yoshie, H. Abe, K. Tada, M. Nakamura, K. Sugamura, and S. Takano J. Immunol. 162 1999 1278
2. W.S. Powell Prostaglandins Leukot. Essent. Fatty Acids 69 2003 179
3. R. Pettipher Br. J. Pharmacol. 153 2008 S191 and references therein
4. H. Hirai, K. Tanaka, O. Yoshie, K. Ogawa, K. Kenmotsu, Y. Takamori, M. Ichimasa, K. Sugamura, M. Nakamura, S. Takano, and K. Nagata J. Exp. Med. 193 2001 255
5. M. Shichijo, H. Sugimoto, K. Nagao, H. Inbe, J.A. Encinas, K. Takeshita, K.B. Bacon, and F. Gantner J. Pharmacol. Exp. Ther. 307 2003 518
6. L. Xue, A. Barrow, and R. Pettipher J. Immunol. 182 2009 7580
7. L. Xue, S.L. Gyles, F.R. Wettey, L. Gazi, E. Townsend, M.G. Hunter, and R. Pettipher J. Immunol. 175 2005 6531
8. L.A. Garza, Y. Liu, Z. Yang, B. Alagesan, J.A. Lawson, S.M. Norberg, D.E. Loy, T. Zhao, H.B. Blatt, D.C. Stanton, L. Carrasco, G. Ahluwalia, S.M. Fischer, G.A. FitzGerald, and G. Cotsarelis Sci. Trans. Med. 4 2012 126ra34
9. P. Norman Exp. Opin. Invest. Drugs 23 2014 55
10. R. Pettipher, and M. Whittaker J. Med. Chem. 55 2012 2915
11. J.J. Chen, and A.L. Budelsky Prog. Med. Chem. 50 2011 49
12. L. Burgess Annu. Rep. Med. Chem. 46 2011 119
13. T. Ulven, and E. Kostenis Expert Opin. Ther. Pat. 20 2010 1505
14. R.S. Obach, F. Lombardo, and N.J. Waters Drug Metab. Dispos. 36 2008 1385
15. G. Dahl, and T. Akerud Drug Discovery Today 18 2013 697
16. G. Vauquelin, and I. Van Liefde Trends Pharm. Sci. 27 2006 355
17. P.J. Tummino, and R.A. Copeland Biochemistry 47 2008 5481
18. R.A. Copeland, D.C. Pompliano, and T.D. Meek Nat. Rev. Drug Disc. 5 2006 730
19. R.A. Copeland Future Med. Chem. 3 2011 1491
20. D.C. Swinney Int. J. Pharm. Med. 22 2008 23
21. D.C. Swinney Curr. Opin. Drug Discov. Dev. 12 2009 31
22. R.A. Copeland Expert Opin. Drug Discov. 5 2010 305
23. R. Zhang, and F. Monsma Expert Opin. Drug Discov. 5 2010 1023
24. For example, see: S. Núñez, J. Venhorst, and C.G. Kruse Drug Discovery Today 17 2012 10
25. H. Lu, and P.J. Tonge Curr. Opin. Chem. Biol. 14 2010 467
26. For example, see: L.T. Gooljarsingh, C. Fernandes, K. Yan, H. Zhang, M. Grooms, K. Johanson, R.H. Sinnamon, R.B. Kirkpatrick, J. Kerrigan, T. Lewis, M. Arnone, A.J. King, Z. Lai, R.A. Copeland, and P.J. Tummino Proc. Natl. Acad. Sci. U.S.A. 102 2006 7625
27. (b) P. Seeman Expert Opin. Ther. Targets 20 2010 1505
28. G. Tresadern, J.M. Bartolomé, G.J. Macdonald, and X. Langlois Bioorg. Med. Chem. 19 2011 2231
29. D.C. Miller, G. Lunn, P. Jones, Y. Sabnis, N.L. Davies, and P. Driscoll Med. Chem. Commun. 3 2012 449
30. A.C. Pan, D.W. Borhani, R.O. Dror, and D.E. Shaw Drug Discovery Today 18 2013 667
31. P. Magotti, D. Ricklin, H. Qu, Y.-Q. Wu, Y.N. Kaznessis, and J.D. Lambris J. Mol. Recognit. 22 2009 495
32. P.A. Glossop, C.A.L. Watson, D.A. Price, M.E. Bunnage, D.S. Middleton, A. Wood, K. James, D. Roberts, R.S. Strang, M. Yeadon, C. Perros-Huguet, N.P. Clarke, M.A. Trevethick, I. Machin, E.F. Stuart, S.M. Evans, A.C. Harrison, D.A. Fairman, B. Agoram, J.L. Burrows, N. Feeder, C.K. Fulton, B.R. Dillon, D.A. Entwistle, and F.J. Spence J. Med. Chem. 54 2011 6888
33. D. Guo, Mulder-Krieger, A.P. IJzerman, and L.H. Heitman Br. J. Pharmacol. 2012 1846 166
34. E.V. Schneider, J. Böttcher, R. Huber, K. Maskos, and L. Neumann Proc. Natl. Acad. Sci. U.S.A. 110 2013 8081
35. C.S. Tautermann, T. Kiechle, D. Seeliger, S. Diehl, E. Wex, R. Banholzer, F. Gantner, M.P. Pieper, and P. Casarosa J. Med. Chem. 56 2013 8746
36. M. Vilums, A.J.M. Zweemer, Z. Yu, H. de Vries, J.M. Hillger, H. Wapenaar, I.A.E. Bollen, F. Barmare, R. Gross, J. Clemens, P. Krenitsky, J. Brussee, D. Stamos, J. Saunders, L.H. Heitman, and A.P. IJzerman J. Med. Chem. 56 2013 7706
37. J. Louvel, D. Guo, M. Agliardi, T.A.M. Mocking, R. Kars, T.P. Pham, L. Xia, H. de Vries, J. Brussee, L.H. Heitman, and A.P. IJzerman J. Med. Chem. 57 2014 3212
38. Alonso, J. A.; Andrés, M.; Bravo, M.; Buil, M. A.; Calbet, M.; Castro, J.; Eastwood, P. R.; Eichhorn, P.; Esteve, C.; Gómez, E.; González, J.; Mir, M.; Petit, S.; Roberts, R. S.; Vidal, B.; Vidal, L.; Vilaseca, P.; Zanuy. M. Bioorg. Med. Chem. Lett. Accepted for publication.
39. Alonso, J. A.; Andrés, M.; Bravo, M.; Calbet, M.; Eastwood, P. R.; Eichhorn, P.; Esteve, C.; Ferrer, M.; Gómez, E.; González, J.; Mir, M.; Moreno, I.; Petit, S.; Roberts, R. S.; Sevilla, S.; Vidal, B.; Vidal, L.; Vilaseca, P.; Zanuy. M. Bioorg. Med. Chem. Lett. Accepted for publication.
40. K.J. Stebbins, A.R. Broadhead, L.D. Correa, J.M. Scott, Y.P. Truong, B.A. Stearns, J.H. Hutchinson, P. Prasit, J.F. Evans, and D.S. Lorrain Eur. J. Pharmacol. 638 2010 142
41. Potency shifts have been observed in CRTh2 in several chemical series: M. Andrés, M. Bravo, M.A. Buil, M. Calbet, J. Castro, T. Domènech, P. Eichhorn, M. Ferrer, E. Gómez, M.D. Lehner, I. Moreno, R.S. Roberts, and S. Sevilla Bioorg. Med. Chem. Lett. 23 2013 3349
42. S. Crosignani, A. Prêtre, C. Jorand-Lebrun, G. Fraboulet, J. Seenisamy, J. Kallikat Augustine, M. Missotten, Y. Humbert, C. Cleva, N. Abla, H. Daff, O. Schott, M. Schneider, F. Burgat-Charvillon, D. Rivron, I. Hamernig, J.-F. Arrighi, M. Gaudet, S.C. Zimmerli, P. Juillard, and Z. Zoe Johnson J. Med. Chem. 54 2011 7299
43. S. Grimwood, and P.R. Hartig Pharmacol. Ther. 122 2009 281
44. K.A. Brameld, B. Kuhn, D.C. Reuter, and M. Stahl J. Chem. Inf. Model. 48 2008 1 and references cited therein