1-Heteroaryl-3-phenoxypropan-2-ones as inhibitors of cytosolic phospholipase A2α and fatty acid amide hydrolase: Effect of the replacement of the ether oxygen with sulfur and nitrogen moieties on enzyme inhibition and metabolic stability

Bioorganic and Medicinal Chemistry

Volumn 23, Issue 10, 2015, Pages 2579-2592

  Sundermann, Tom ^a   Fabian, Jörg ^a   Hanekamp, Walburga ^a   Lehr, Matthias ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Aldo keto reductase; Benzotriazole; Carbonyl reductase; Cytochrome P450; Cytosolic phospholipase A2 ; Fatty acid amide hydrolase; Indole 5 carboxylic acid; Inhibitors; Metabolic stability; Short chain dehydrogenase reductase

Indexed keywords

AMIDASE; ANALGESIC AGENT; CARBOXYLIC ACID; ENZYME INHIBITOR; FATTY-ACID AMIDE HYDROLASE; INDOLE DERIVATIVE; KETONE; NITROGEN; NONSTEROID ANTIINFLAMMATORY AGENT; OXYGEN; PHOSPHOLIPASE A2 GROUP IV; SULFUR;

ANIMAL; ANTAGONISTS AND INHIBITORS; BIOTRANSFORMATION; BRAIN CHEMISTRY; CHEMISTRY; DRUG STABILITY; LIVER MICROSOME; PIG; RAT; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

AMIDOHYDROLASES; ANALGESICS; ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; BIOTRANSFORMATION; BRAIN CHEMISTRY; CARBOXYLIC ACIDS; DRUG STABILITY; ENZYME INHIBITORS; GROUP IV PHOSPHOLIPASES A2; INDOLES; KETONES; MICROSOMES, LIVER; NITROGEN; OXYGEN; RATS; STRUCTURE-ACTIVITY RELATIONSHIP; SULFUR; SWINE;

EID: 84937758737     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2015.03.033     Document Type: Article

References (39)

1. S.P. Khanapure, D.S. Garvey, D.R. Janero, and L.G. Letts Curr. Top. Med. Chem. 7 2007 311
2. J.E. Schlosburg, S.G. Kinsey, and A.H. Lichtman AAPS J. 11 2009 39
3. T. Hirabayashi, T. Murayama, and T. Shimizu Biol. Pharm. Bull. 27 2004 1168
4. J. Bonventre Trends Immunol. 25 2004 116
5. M. Lehr RSC Drug Discovery Ser. (Anti-Inflamm. Drug Discovery) 26 2012 35
6. E.A. Dennis, J. Cao, Y.H. Hsu, V. Magrioti, and G. Kokotos Chem. Rev. 111 2011 6130
7. V. Magrioti, and G. Kokotos Expert Opin. Ther. Pat. 23 2013 333
8. L.A. Trimble, I.P. Street, H. Perrier, N.M. Tremblay, P.K. Weech, and M.A. Bernstein Biochemistry 32 1993 12560
9. I.P. Street, H.K. Lin, F. Laliberte, F. Ghomashchi, Z. Wang, H. Perrier, N.M. Tremblay, Z. Huang, P.K. Weech, and M.H. Gelb Biochemistry 32 1993 5935
10. Z. Huang, S. Liu, I. Street, F. Laliberte, K. Abdullah, S. Desmarais, Z. Wang, B. Kennedy, P. Payette, D. Riendeau, P. Weech, and M. Gresser Mediat. Inflamm. 3 1994 307
11. J.C. McKew, K.L. Lee, M.W. Shen, P. Thakker, M.A. Foley, M.L. Behnke, B. Hu, F.W. Sum, S. Tam, Y. Hu, L. Chen, S.J. Kirincich, R. Michalak, J. Thomason, M. Ipek, K. Wu, L. Wooder, M.K. Ramarao, E.A. Murphy, D.G. Goodwin, L. Albert, X. Xu, F. Donahue, M.S. Ku, J. Keith, C.L. Nickerson-Nutter, W.M. Abraham, C. Williams, M. Hegen, and J.D. Clark J. Med. Chem. 51 2008 3388
12. K. Seno, T. Okuno, K. Nishi, Y. Murakami, F. Watanabe, T. Matsuura, M. Wada, Y. Fujii, M. Yamada, T. Ogawa, T. Okada, H. Hashizume, M. Kii, S. Hara, S. Hagishita, S. Nakamoto, K. Yamada, Y. Chikazawa, M. Ueno, I. Teshirogi, T. Ono, and M. Ohtani J. Med. Chem. 43 2000 1041
13. S. Connolly, C. Bennion, S. Botterell, P.J. Croshaw, C. Hallam, K. Hardy, P. Hartopp, C.G. Jackson, S.J. King, L. Lawrence, A. Mete, D. Murray, D.H. Robinson, G.M. Smith, L. Stein, I. Walters, E. Wells, and W.J. Withnall J. Med. Chem. 45 2002 1348
14. G. Kokotos, D.A. Six, V. Loukas, T. Smith, V. Constantinou-Kokotou, D. Hadjipavlou-Litina, S. Kotsovolou, A. Chiou, C.C. Beltzner, and E.A. Dennis J. Med. Chem. 47 2004 3615
15. J. Ludwig, S. Bovens, C. Brauch, A. Schulze Elfringhoff, and M. Lehr J. Med. Chem. 49 2006 2611
16. M.K. McKinney, and B.F. Cravatt Annu. Rev. Biochem. 74 2005 411
17. G. Labar, and C. Michaux Chem. Biodivers. 4 2007 1882
18. F. Fezza, C. De Simone, D. Amadio, and M. Maccarrone Subcell. Biochem. 49 2008 101
19. S.M. Saario, and J.T. Laitinen Basic Clin. Pharmacol. Toxicol. 101 2007 287
20. M. Seierstad, and J.G. Breitenbucher J. Med. Chem. 51 2008 7327
21. S. Vandevoorde Curr. Top. Med. Chem. 8 2008 247
22. T. Bisogno, and M. Maccarrone Expert Opin. Drug Discovery 8 2013 509
23. M. Feledziak, D.M. Lambert, J. Marchand-Brynaert, and G.G. Muccioli Recent Pat. CNS Drug Discovery 7 2012 49
24. L. Forster, J. Ludwig, M. Kaptur, S. Bovens, A. Schulze Elfringhoff, A. Holtfrerich, and M. Lehr Bioorg. Med. Chem. 18 2010 945
25. S. Zahov, A. Drews, M. Hess, A. Schulze Elfringhoff, and M. Lehr ChemMedChem 6 2011 544
26. W. Hanekamp, and M. Lehr J. Chromatogr., B 900 2012 79
27. A. Holtfrerich, W. Hanekamp, and M. Lehr Eur. J. Med. Chem. 63 2013 64
28. S. Bovens, A. Schulze Elfringhoff, M. Kaptur, D. Reinhardt, M. Schäfers, and M. Lehr J. Med. Chem. 53 2010 8298
29. J. Fabian, W. Hanekamp, M.H. Thomas, J.L. Olivier, and M. Lehr Chem. Biol. Interact. 206 2013 356
30. S.C. Khojasteh, S. Prabhu, J.R. Kenny, J.S. Halladay, and A.Y. Lu Eur. J. Drug Metab. Pharmacokinet. 36 2011 1
31. Trambitas, C.; Holloway, A.; Cranksshaw, D. Effects of Cytochrome p450 Inhibitors on the Biotransformation of Fluorogenic Substrates by Adult Male Rat Liver Microsomes. Winter Meeting of the British Pharmacological Society in Brighton, 2007; Abstract 082P, http://www.pa2online.org/abstracts/Vol5Issue2abst082P.pdf.
32. V.A. Eagling, J.F. Tjia, and D.J. Back Br. J. Clin. Pharmacol. 45 1998 107
33. E. Makaji, C.S. Trambitas, P. Shen, A.C. Holloway, and D.J. Crankshaw Toxicol. Sci. 113 2010 293
34. V.T. Ly, and B. Brock Chem. Biol. Interact. 193 2011 109
35. S. Murray, A.O. Odupitan, B.P. Murray, A.R. Boobis, and R.J. Edwards Xenobiotica 31 2001 135
36. U.C. Oppermann, and E. Maser Toxicology 144 2000 71
37. P. Malátková, E. Maser, and V. Wsól Curr. Drug Metab. 11 2010 639
38. M.J. Cox Rosemond Measurement of Xenobiotic Carbonyl Reduction in Human Liver Fractions. Current Protocols in Toxicology 2005 John Wiley & Sons pp 4.17.1-4.17.7
39. Z. Tong, A. Chandrasekaran, H. Li, Y. Rotshteyn, J.C. Erve, W. Demaio, R. Talaat, T. Hultin, and J. Scatina Drug Metab. Dispos. 38 2010 801