Benzoxazinones as potent positive allosteric AMPA receptor modulators: Part I

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 13, 2011, Pages 3923-3926

  Mueller, Rudolf ^a   Li, Yong Xin ^a   Hampson, Aidan ^a   Zhong, Sheng ^a   Harris, Clayton ^a   Marrs, Christopher ^a   Rachwal, Stanislaw ^a   Ulas, Jolanta ^a   Nielsson, Lena ^a   Rogers, Gary ^a  

^a Cortex Pharmaceuticals Inc ^*  (United States)

Author keywords

AMPA; Modulator; Receptor; Synthesis

Indexed keywords

AMPA RECEPTOR; AMPA RECEPTOR ANTAGONIST; AMPAKINE; ANIRACETAM; BENZOXAZINONE DERIVATIVE; CX 614; DIOXIN; UNCLASSIFIED DRUG;

ALLOSTERISM; ANIMAL CELL; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DRUG POTENCY; DRUG SYNTHESIS; IN VITRO STUDY; NONHUMAN; RING CLOSING METATHESIS; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

ALLOSTERIC REGULATION; ANIMALS; BENZOXAZINES; MOLECULAR STRUCTURE; NOOTROPIC AGENTS; PROSENCEPHALON; PYRROLIDINONES; RATS; RECEPTORS, AMPA; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 79958735578     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.05.026     Document Type: Article

References (49)

1. Morrow, J. A.; Maclean, J. K. F.; Jamieson, C. Curr. Opin. Drug Discovery Dev. 2006, 9, 571.
2. Jin, R.; Clark, S.; Weeks, A. M.; Dudman, J. T.; Gouaux, E.; Partin, K. M. J. Neuroscience 2005, 25, 9027.
3. Arai, A. C.; Kessler, M. Curr. Drug Targets 2007, 8, 583.
4. Harpsøe, K.; Liljefors, T.; Balle, T. J. Mol. Graphics Modell. 2008, 26, 874.
5. Harpsøe, K.; Varming, T.; Gouliaev, A. H.; Peters, D.; Liljefors, T. J. Mol. Graphics Modell. 2007, 26, 213.
6. Sun, Y.; Olson, R.; Horning, M.; Armstrong, N.; Mayer, M.; Gouaux, E. Nature 2002, 417, 245.
7. Arai, A. C.; Xia, Y.-F.; Rogers, G.; Lynch, G.; Kessler, M. J. Pharmacol. Exp. Ther. 2002, 303, 1075.
8. Marenco, S.; Weinberger, D. R. CNS Drugs 2006, 20, 173.
9. Alt, A.; Nisenbaum, E. S.; Bleakman, D.; Witkin, J. M. Biochem. Pharmacol. 2006, 77, 1273.
10. Kanju, P. M.; Parameshwaran, K.; Sims, C.; Bahr, B. A.; Shonesy, B. C.; Suppiramaniam, V. Exp. Neurol. 2008, 214, 55.
11. O'Neill, M. J.; Bleakman, D.; Zimmerman, D. M.; Nisenbaum, E. S. Curr. Drug Targets: CNS Neurol. Disord. 2004, 3, 181.
12. Sanacora, G.; Zarate, C. A.; Krystal, J. H.; Manji, H. K. Nature Rev. 2008, 7, 426.
13. Hashimoto, K. Brain Res. Rev. 2009, 61, 105.
14. Lauterborn, J. C.; Lynch, G.; Vanderklish, P.; Arai, A.; Gall, C. M. J. Neurosci. 2000, 8.
15. Lauterborn, J. C.; Pineda, E.; Chen, L. Y.; Ramirez, E. A.; Lynch, G.; Gall, C. M. Neuroscience 2009, 159, 283.
16. Lauterborn, J. C.; Troung, G.; Baudry, M.; Bi, X.; Lynch, G.; Gall, C. J. Pharmacol. Exp. Ther. 2003, 307, 297.
17. Lynch, G. Curr. Opin. Pharmacol. 2004, 4, 4.
18. Lynch, G.; Gall, C. M. Trends Neurosci. 2006, 29, 554.
19. O'Neill, M. J.; Dix, S. IDrugs 2007, 10, 185.
20. Arai, A.; Kessler, M.; Rogers, G.; Lynch, G. J. Pharmacol. Exp. Ther. 1996, 278, 627.
21. Staubli, U.; Rogers, G.; Lynch, G. Proc. Natl. Acad. Sci. 1994, 91, 777.
22. Raymond, C. R. Trends Neurosci. 2007, 30, 167.
23. Lamprecht, R.; LeDoux, J. Nature Rev., Neurosci. 2004, 5, 45.
24. Lynch, M. A. Physiol. Rev. 2004, 84, 87.
25. Bloss, E. B.; Hunter, R. G.; Waters, E. M.; Munoz, C.; Bernard, K.; McEwen, B. S. Exp. Neurol. 2008, 210, 109.
26. Francotte, P.; De Tullio, P.; Goffin, E.; Dintilhac, G.; Graindorge, E.; Fraikin, P.; Lestage, P.; Danober, L.; Thomas, J. Y.; Caignard, D. H.; Pirotte, B. J. Med. Chem. 2007, 50, 3153.
27. Zivcovic, I.; Thompson, D. M.; Bertolino, M.; Uzunov, D.; Dibella, M.; Costa, E.; Guidotti, A. Pharmacol. Exp. Ther. 2009, 272, 300.
28. Murray, T. K.; Whalley, K.; Robinson, C. S.; Ward, M. A.; Hicks, C. A.; Lodge, D.; Vandergriff, J. L.; Baumbarger, P.; Siuda, E.; Gates, M.; Ogden, A. M.; Skolnick, P.; Zimmerman, D. M.; Nisenbaum, E. S.; Bleakman, D.; O'Neill, M. J. Pharmacol. Exp. Ther. 2003, 306, 752.
29. Francotte, P.; Tullio, P.; Podona, T.; Diouf, O.; Fraikin, P.; Lestage, P.; Danober, L.; Thomas, J.-Y.; Caigard, D.-H.; Pirotte, B. Bioorg. Med. Chem. 2008, 16, 9948.
30. Zarrinmayeh, H.; Bleakman, D.; Gates, M. R.; Yu, H.; Zimmerman, D. M.; Ornstein, P. L.; McKennon, T.; Arnold, M. B.; Wheeler, W. J.; Skolnick, P. J. Med. Chem. 2001, 44, 302.
31. Magnus, N. A.; Stazak, M. A.; Udodong, U. E.; Wepsiec, J. P. Org. Process Res. Dev. 2006, 10, 899.
32. Phillips, D.; Sonnenberg, J.; Arai, A. C.; Vaswani, R.; Krutzik, P. O.; Kleisli, T.; Kessler, M.; Granger, R.; Lynch, G.; Chamberlin, A. R. Bioorg. Med. Chem. 2002, 10, 1229.
33. Zarrinmayeh, H.; Tromiczak, E.; Zimmerman, D. M.; Rankl, N.; Ho, K. H.; Dominguez, E.; Castano, A.; Escribano, A.; Fernandez, C.; Jimenez, A.; Hornback, W. J.; Nisenbaum, E. S. Bioorg. Med. Chem. Lett. 2006, 20, 5203.
34. Fernandez, M.-C.; Castano, A.; Dominguez, E.; Escribano, A.; Jiang, D.; Jimenez, A.; Hong, E.; Hornback, W. J.; Nisenbaum, E. S.; Rankl, N.; Tromiczak, E.; Vaught, G.; Zarrinmayeh, H.; Zimmerman, D. M. Bioorg. Med. Chem. Lett. 2006, 20, 5057.
35. Ptak, C. P.; Ahmaed, A. H.; Oswald, R. E. Biochemistry 2009, 8594.
36. Thewlis, K. M.; Aldegheri, L.; Harries, M. H.; Mookherjee, C.; Oliosi, B.; Ward, S. E. Bioorg. Med. Chem. Lett. 2010, 16, 7116.
37. Ward, S. E.; Harries, M.; Aldegheri, L.; Austin, N. E.; Ballantine, S.; Ballini, E.; Bradley, D. M.; Bax, B. D.; Clarke, B. P.; Harris, A. J.; Harrison, S. A.; Melarange, R. A.; Mookherjee, C.; Mosley, J.; Dal Negro, G.; Oliosi, B.; Smith, K. J.; Thewlis, K. M.; Woolard, P. M.; Yusaf, S. P. J. Med. Chem. 2011, 54, 78.
38. Ward, S. E.; Harries, M.; Aldegheri, L.; Andreotti, D.; Ballantine, S.; Bax, B. D.; Harris, A. J.; Harker, A. J.; Lund, J.; Melarange, R.; Mingardi, A.; Mookherjee, C.; Mosley, J.; Neve, M.; Oliosi, B.; Profeta, R.; Smith, K. J.; Smith, P. W.; Spada, S.; Thewlis, K. M.; Yusaf, S. P. J. Med. Chem. 2010, 53, 5801.
39. Ward, S. E.; Bax, B. D.; Harries, M. Br. J. Pharmacol. 2010, 160, 181.
40. Grove, S. J. A.; Jamieson, C.; Maclean, J. K. F.; Morrow, J. A.; Rancovic, Z. J. Med. Chem. 2010, 53, 7271.
41. Jamieson, C.; Maclean, J. K. F.; Brown, C. I.; Campbell, R. A.; Gillen, K. J.; Gillespie, J.; Kazemier, B.; Kiczun, M.; Lamont, Y.; Lyons, A. J.; Moir, E. M.; Morrow, J. A.; Pantling, J.; Rankovic, Z.; Smith, L. Bioorg. Med. Chem. Lett. 2011, 21, 805.
42. Jamieson, C.; Campbell, R. A.; Cumming, I. A.; Gillen, K. J.; Gillespie, J.; Kazemier, B.; Kiczun, M.; Lamont, Y.; Lyons, A. J.; Maclean, J. K. F.; Martin, F.; Moir, E. M.; Morrow, J. A.; Pantling, J.; Rancovic, Z.; Smith, L. Bioorg. Med. Chem. Lett. 2010, 20, 6072.
43. Jamieson, C.; Basten, S.; Campbell, R. A.; Cumming, I. A.; Gillen, K. J.; Gillespie, J.; Kazemier, B.; Kiczun, M.; Lamont, Y.; Lyons, A. J.; Maclean, J. K. F.; Moir, E. M.; Morrow, J. A.; Papakosta, M.; Rancovic, Z. Bioorg. Med. Chem. Lett. 2010, 20, 5753.
44. Cannazza, G.; Jozowiak, K.; Parenti, C.; Braghiroli, D.; Carrozzo, M. M.; Puia, G.; Losi, G.; Baraldi, M.; Lindnaer, W.; Wainer, I. W. Bioorg. Med. Chem. Lett. 2009, 19, 1254.
45. 2x value is defined as the concentration (in lM) of the compound required to double the steady-state current induced by glutamate.
46. 2 gas and Crabtree's catalyst. The active, tritiated enantiomer was synthesized accordingly, isolated by HPLC (Chiralpak IA) and used in binding studies.
47. Schweizer, E. E.; Liehr, J.; Monaco, D. J. J. Org. Chem. 1968, 33, 2416.
48. Rogers, G. A.; Allan, M.; Harris, C.; Huang, J.; Marrs, C. M.; Mueller, R.; Rachwal, S. U.S. 7799913, 2010.
49. In vitro slice assay: Transverse 300-400 μM hippocampal slices were taken from adult male Sprague-Dawley rats (4-6 week old) and incubated on nylon net in a rapid-flow linear interface recording chamber. The chamber was perfused with oxygenated artificial cerebral spinal fluid (ACSF). Field EPSP (excitatory postsynaptic potential) recordings were made with glass electrodes filled with 2 M NaCl (1-5 megaohm), placed in the stratum radiatum or stratum oriens of CA1. Electrical stimuli were produced with twisted bipolar nichrome wire electrodes in the Schaffer-commissural fiber afferents. EPSP was induced by activating Schaffer-commissural fiber using pair pulse stimulation with a pulse interval at 200 ms delivered at 0.05 Hz. The amplitude, half-width and area were measured for each response and plotted against time. After a stable baseline was established (20-30 min), test compound was infused for 30 min to observe the effect. Then the solution was switched to control ACSF and continued to record until drug effect was washed back to the baseline. Most of the compounds were made into stock solution by dissolving in DMSO then adding into ACSF. If DMSO concentration has to be >0.05%, DMSO was also added into the control ACSF. Both Control ACSF and test compound were infused to the recording chamber bath by gravity infusion system.