Heteroaryl urea inhibitors of fatty acid amide hydrolase: Structure-mutagenicity relationships for arylamine metabolites

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 24, 2012, Pages 7357-7362

  Tichenor, Mark S ^a   Keith, John M ^a   Jones, William M ^a   Pierce, Joan M ^a   Merit, Jeff ^a   Hawryluk, Natalie ^a   Seierstad, Mark ^a   Palmer, James A ^a   Webb, Michael ^a   Karbarz, Mark J ^a   Wilson, Sandy J ^a   Wennerholm, Michelle L ^a   Woestenborghs, Filip ^a   Beerens, Dominiek ^a   Luo, Lin ^a   Brown, Sean M ^a   Boeck, Marlies De ^a   Chaplan, Sandra R ^a   Breitenbucher, J Guy ^a  

^a JANSSEN RESEARCH AND DEVELOPMENT   (Belgium)

Author keywords

Ames II; FAAH; Fatty acid amide hydrolase; Heteroaryl amine; Mutagenic; Urea

Indexed keywords

AROMATIC AMINE; ELECTROPHILE; FATTY ACID AMIDASE; FATTY ACID AMIDASE INHIBITOR; ISOXAZOLO[5,4 C]PYRIDIN 3 YLAMINE; SERINE; UNCLASSIFIED DRUG;

ARTICLE; ENZYME ACTIVE SITE; MUTAGENICITY; STRUCTURE ACTIVITY RELATION;

AMIDOHYDROLASES; AMINES; ANIMALS; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; HUMANS; MIXED FUNCTION OXYGENASES; MOLECULAR STRUCTURE; MUTAGENICITY TESTS; MUTAGENS; RATS; STRUCTURE-ACTIVITY RELATIONSHIP; UREA;

EID: 84870248586     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.10.076     Document Type: Article

References (56)

1. M.K. McKinney, and B.F. Cravatt Annu. Rev. Biochem. 74 2005 411
2. B.F. Cravatt, K. Demarest, M.P. Patricelli, M.H. Bracey, D.K. Giang, B.R. Martin, and A.H. Lichtman Proc. Natl. Acad. Sci. U.S.A. 98 2001 9371
3. K. Ahn, D.S. Johnson, and B.F. Cravatt Expert Opin. Drug Disc. 4 2009 763
4. M. Seierstad, and J.G. Breitenbucher J. Med. Chem. 51 2008 7327
5. G. Palermo, D. Branduardi, M. Masetti, A. Lodola, M. Mor, D. Piomelli, A. Cavalli, and M. De Vivo J. Med. Chem. 54 2011 6612
6. M. Mileni, D.S. Johnson, Z. Wang, D.S. Everdeen, M. Liimatta, B. Pabst, K. Bhattacharya, R.A. Nugent, S. Kamtekar, B.F. Cravatt, K. Ahn, and R.C. Stevens Proc. Natl. Acad. Sci. U.S.A. 105 2008 12820
7. M. Mileni, S. Kamtekar, D.C. Wood, T.E. Benson, B.F. Cravatt, and R.C. Stevens J. Mol. Biol. 400 2010 743
8. G. Tian, K.A. Paschetto, F. Gharahdaghi, E. Gordon, D.E. Wilkins, X. Luo, and C.W. Scott Biochemistry 50 2011 6867
9. D.J. Gustin, Z. Ma, X. Min, Y. Li, C. Hedberg, C. Guimaraes, A.C. Porter, M. Lindstrom, D. Lester-Zeiner, G. Xu, T.J. Carlson, S. Xiao, C. Meleza, R. Connors, Z. Wang, and F. Kayser Bioorg. Med. Chem. Lett. 21 2011 2492
10. X. Min, S.T. Thibault, A.C. Porter, D.J. Gustin, T.J. Carlson, H. Xu, M. Lindstrom, G. Xu, C. Uyeda, Z. Ma, Y. Li, F. Kayser, N.P. Walker, and Z. Wang Proc. Natl. Acad. Sci. U.S.A. 108 2011 7379
11. C.W. Scott, G. Tian, X.H. Yu, K.A. Paschetto, D.E. Wilkins, L. Meury, C.Q. Cao, J. Varnes, and P.D. Edwards Eur. J. Pharmacol. 667 2011 74
12. M.H. Potashman, and M.E. Duggan J. Med. Chem. 52 2009 1231
13. D. Fegley, S. Gaetani, A. Duranti, A. Tontini, M. Mor, G. Tarzia, and D.J. Piomelli Pharmacol. Exp. Ther. 313 2005 352
14. D.S. Johnson, C. Stiff, S.E. Lazerwith, S.R. Kesten, L.K. Fay, M. Morris, D. Beidler, M.B. Liimatta, S.E. Smith, D.T. Dudley, N. Sadagopan, S.N. Bhattachar, S.J. Kesten, T.K. Nomanbhoy, B.F. Cravatt, and K. Ahn ACS Med. Chem. Lett. 2 2011 91
15. M. Mor, S. Rivara, A. Lodola, P.V. Plazzi, G. Tarzia, A. Duranti, A. Tontini, G. Piersanti, S. Kathuria, and D. Piomelli J. Med. Chem. 47 2004 4998
16. S. Kathuria, S. Gaetani, D. Fegley, F. Valino, A. Duranti, A. Tontini, M. Mor, G. Tarzia, G. La Rana, A. Calignano, A. Giustino, M. Tattoli, M. Palmery, V. Cuomo, and D. Piomelli Nat. Med. 9 2003 76
17. D. Zhang, A. Saraf, T. Kolasa, P. Bhatia, G.Z. Zheng, M. Patel, G.S. Lannoye, P. Richardson, A. Stewart, J.C. Rogers, J.D. Brioni, and C.S. Surowy Neuropharmacology 52 2007 1095
18. M.J. Niphakis, D.S. Johnson, T.E. Ballard, C. Stiff, and B.F. Cravatt ACS Chem. Neurosci. 3 2012 418
19. Matsumoto, T.; Kori, M.; Miyazaki, J.; Kiyota, Y. Patent WO 2006/054652.
20. M.J. Karbarz, L. Luo, L. Chang, C.-S. Tham, J.A. Palmer, S.J. Wilson, M.L. Wennerholm, S.M. Brown, B.P. Scott, R.L. Apodaca, J.M. Keith, J. Wu, J.G. Breitenbucher, S.R. Chaplan, and M. Webb Anesth. Analg. 108 2008 316
21. Apodaca, R.; Breitenbucher, J. G.; Pattabiraman, K.; Seierstad, M.; Xiao, W. Patent US 2007/0004741.
22. J.M. Keith, R. Apodaca, W. Xiao, M. Seierstad, K. Pattabiraman, J. Wu, M. Webb, M.J. Karbarz, S. Brown, S. Wilson, B. Scott, C.S. Tham, L. Luo, J. Palmer, M. Wennerholm, S. Chaplan, and J.G. Breitenbucher Bioorg. Med. Chem. Lett. 18 2008 4838
23. K. Ahn, D.S. Johnson, L.R. Fitzgerald, M. Liimatta, A. Arendse, T. Stevenson, E.T. Lund, R.A. Nugent, T.K. Nomanbhoy, J.P. Alexander, and B.F. Cravatt Biochemistry 46 2007 13019
24. Ishii, T.; Sugane, T.; Kakefuda, A.; Takahashi, T.; Kanayama, T.; Sato, K.; Kuriwaki, I.; Kitada, C.; Suzuki, J. Patent WO 2008/023720.
25. K. Ahn, D.S. Johnson, M. Mileni, D. Beidler, J.Z. Long, M.K. McKinney, E. Weerapana, N. Sadagopan, M. Liimatta, S.E. Smith, S. Lazerwith, C. Stiff, S. Kamtekar, K. Bhattacharya, Y. Zhang, S. Swaney, K. Van Becelaere, R.C. Stevens, and B.F. Cravatt Chem. Biol. 16 2009 411
26. D.S. Johnson, K. Ahn, S. Kesten, S.E. Lazerwith, Y. Song, M. Morris, L. Fay, T. Gregory, C. Stiff, J.B. Dunbar Jr., M. Liimatta, D. Beidler, S. Smith, T.K. Nomanbhoy, and B.F. Cravatt Bioorg. Med. Chem. Lett. 19 2009 2865
27. K. Ahn, S.E. Smith, M.B. Liimatta, D. Beidler, N. Sadagopan, D.T. Dudley, T. Young, P. Wren, Y. Zhang, S. Swaney, K. Van Becelaere, J.L. Blankman, D.K. Nomura, S.N. Bhattachar, C. Stiff, T.K. Nomanbhoy, E. Weerapana, D.S. Johnson, and B.F.J. Cravatt Pharmacol. Exp. Ther. 338 2011 114
28. Apodaca, R.; Breitenbucher, J. G.; Hawryluk, N. A.; Jones, W. M.; Keith, J. M.; Merit, J. E.; Tichenor, M. S.; Timmons, A. K. Patent WO 2008/153752.
29. Breitenbucher, J. G.; Keith, J. M.; Tichenor, M. S.; Chambers, A. L.; Jones, W. M.; Hawryluk, N. A.; Timmons, A. K.; Merit, J. E.; Seierstad, M. J. Patent WO 2010/068453.
30. Breitenbucher, J. G.; Keith, J. M.; Tichenor, M. S.; Chambers, A. L.; Jones, W. M.; Hawryluk, N. A.; Timmons, A. K.; Merit, J. E.; Seierstad, M. J. Patent WO 2010/068452.
31. Keith, J. M.; Apodaca, R.; Tichenor, M.; Xiao, W; Jones, W; Pierce, J.; Seierstad, M; Palmer, J.; Webb, M.; Karbarz, M.; Scott, B.; Wilson, S.; Luo, L.; Wennerholm, M.; Chang, L.; Brown, S.; Rizzolio, M.; Rynberg, R.; Chaplan, S.; Breitenbucher, J. G.; ACS Med. Chem. Lett. 2012, http://dx.doi.org/10.1021/ ml300186g.
32. D.L. Boger, H. Miyauchi, W. Du, C. Hardouin, R.A. Fecik, H. Cheng, I. Hwang, M.P. Hedrick, D. Leung, O. Acevedo, C.R. Guimaraes, W.L. Jorgensen, and B.F. Cravatt J. Med. Chem. 2005 1849 48
33. K. Otrubova, C. Ezzili, and D.L. Boger Bioorg. Med. Chem. Lett. 21 2011 4674
34. J. Garfunkle, C. Ezzili, T.J. Rayl, D.G. Hochstatter, I. Hwang, and D.L. Boger J. Med. Chem. 51 2008 4392
35. F.S. Kimball, F.A. Romero, C. Ezzili, J. Garfunkle, T.J. Rayl, D.G. Hochstatter, I. Hwang, and D.L. Boger J. Med. Chem. 51 2008 937
36. M. Mileni, J. Garfunkle, C. Ezzili, F.S. Kimball, B.F. Cravatt, R.C. Stevens, and D.L. Boger J. Med. Chem. 53 2009 230
37. C. Ezzili, M. Mileni, N. McGlinchey, J.Z. Long, S.G. Kinsey, D.G. Hochstatter, R.C. Stevens, A.H. Lichtman, B.F. Cravatt, E.J. Bilsky, and D.L. Boger J. Med. Chem. 54 2011 2805
38. M. Mileni, J. Garfunkle, C. Ezzili, B.F. Cravatt, R.C. Stevens, and D.L. Boger J. Am. Chem. Soc. 133 2011 4092
39. F. Di Girolamo, L. Campanella, R. Samperi, and A. Bachi Ecotoxicol. Environ. Saf. 72 2009 1601
40. J.H. Harrison Jr., and D. Jollow J. Mol. Pharmacol. 32 1987 423
41. P. Vineis Environ. Health Perspect. 102 1994 7
42. M.A. Jackson, H.F. Stack, and M.D. Waters Mutat. Res. 296 1993 241
43. L.G. Hamann, M.C. Manfredi, C. Sun, S.R. Krystek Jr., Y. Huang, Y. Bi, D.J. Augeri, T. Wang, Y. Zou, D.A. Betebenner, A. Fura, R. Seethala, R. Golla, J.E. Kuhns, J.A. Lupisella, C.J. Darienzo, L.L. Custer, J.L. Price, J.M. Johnson, S.A. Biller, R. Zahler, and J. Ostrowski Bioorg. Med. Chem. Lett. 2007 1860 17
44. K. Mortelmans, and E. Zeiger Mutat. Res. 455 2000 29
45. E. Zeiger Cancer Res. 47 1987 1287
46. S. Fluckiger-Isler, M. Baumeister, K. Braun, V. Gervais, N. Hasler-Nguyen, R. Reimann, J. Van Gompel, H.G. Wunderlich, and G. Engelhardt Mutat. Res. 558 2004 181
47. M. Kamber, S. Fluckiger-Isler, G. Engelhardt, R. Jaeckh, and E. Zeiger Mutagenesis 24 2009 359
48. R. Benigni Chem. Rev. 105 2005 1767
49. J.H. Meerman, and M.L. van de Poll Environ. Health Perspect. 102 1994 153
50. W.G. Humphreys, F.F. Kadlubar, and F.P. Guengerich Proc. Natl. Acad. Sci. U.S.A. 89 1992 8278
51. R. Benigni, L. Passerini, G. Gallo, F. Giorgi, and M. Cotta-Ramusino Environ. Mol. Mutagen. 32 1998 75
52. C. Glende, H. Schmitt, L. Erdinger, G. Engelhardt, and G. Boche Mutat. Res. 498 2001 19
53. A.D. Dunn Z. Chem. 27 1987 337
54. M.G. Palermo Tetrahedron Lett. 37 1996 2885
55. J.P. Paolini, and R.K. Robins J. Heterocycl. Chem. 2 1965 53
56. S.J. Wilson, T.W. Lovenberg, and A.J. Barbier Anal. Biochem. 318 2003 270