Synthesis and evaluation of N-substituted nipecotic acid derivatives with an unsymmetrical bis-aromatic residue attached to a vinyl ether spacer as potential GABA uptake inhibitors

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 11, 2013, Pages 3363-3378

  Quandt, Gabriele ^a   Höfner, Georg ^a   Wanner, Klaus T ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

Aromatic fluoro compounds; Chelation controlled; Fries rearrangement; GABA uptake; Heck reaction; SAR study

Indexed keywords

1 [2 [ 2 (2 BENZYLPHENYL)VINYLOXY]ETHYL]NIPECOTIC ACID; 1 [2 [2 [4 FLUORO 2 (2 FLUOROBENZOYL)PHENYL]VINYLOXY]ETHYL]NIPECOTIC ACID; 1 [2 [2 [4 FLUORO 2 (2 FLUOROBENZYL)PHENYL]VINYLOXY]ETHYL]NIPECOTIC ACID; 1 [2 [2 [4 FLUORO 2 (3 FLUOROBENZOYL)PHENYL]VINYLOXY]ETHYL]NIPECOTIC ACID; 1 [2 [2 [4 FLUORO 2 (4 FLUOROBENZOYL)PHENYL]VINYLOXY]ETHYL]NIPECOTIC ACID; 1 [2 [2 [4 FLUORO 2 (4 FLUOROBENZYL)PHENYL]VINYLOXY]ETHYL]NIPECOTIC ACID; 1 [2 [2 [5 FLUORO 2 (2 FLUOROBENZYL)PHENYL]VINYLOXY]ETHYL]NIPECOTIC ACID; 1 [2 [2 [5 FLUORO 2 (3 FLUOROBENZYL)PHENYL]VINYLOXY]ETHYL]NIPECOTIC ACID; 1 [2 [2 [5 FLUORO 2 (4 FLUOROBENZYL)PHENYL]VINYLOXY]ETHYL]NIPECOTIC ACID; 4 AMINOBUTYRIC ACID A RECEPTOR STIMULATING AGENT; AROMATIC COMPOUND; ETHER DERIVATIVE; ETHYL 1 [2 (VINYLOXY)ETHYL]NIPECOTATE; ETHYL 1 [2 [2 (2 BENZOYLPHENYL)VINYLOXY]ETHYL]NIPECOTATE; ETHYL 1 [2 [2 [4 FLUORO 2 (4 FLUOROBENZOYL)PHENYL]VINYLOXY]ETHYL]NIPECOTATE; ETHYL 1 [2 [2 [4 FLUORO 2 (4 FLUOROBENZYL)PHENYL]VINYLOXY]ETHYL]NIPECOTATE; NIPECOTIC ACID DERIVATIVE; TIAGABINE; UNCLASSIFIED DRUG; VINYL ETHER;

ADD ON THERAPY; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; EPILEPSY;

ANIMALS; ANTICONVULSANTS; BIOLOGICAL TRANSPORT; CELL MEMBRANE; GABA PLASMA MEMBRANE TRANSPORT PROTEINS; GABA UPTAKE INHIBITORS; GAMMA-AMINOBUTYRIC ACID; HEK293 CELLS; HUMANS; MICE; NEUROPROTECTIVE AGENTS; NIPECOTIC ACIDS; STRUCTURE-ACTIVITY RELATIONSHIP; VINYL COMPOUNDS;

MAMMALIA;

EID: 84877811191     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2013.02.056     Document Type: Article

References (38)

1. D.M. Treiman Epilepsia 42 2001 8
2. R.A. Rissman, A.L. De Blas, and D.M. Armstrong J. Neurochem. 103 2007 1285
3. A.A. Todorov, C.B. Kolchev, and A.B. Todorov Clin. J. Pain 21 2005 358
4. A.V. Kalueff, and D.J. Nutt Depress. Anxiety 24 2007 495
5. J. Guastella, N. Nelson, H. Nelson, L. Czyzyk, S. Keynan, M. Miedel, N. Davidson, H. Lester, and B. Kanner Science 249 1990 1303
6. L.A. Borden, K.E. Smith, P.R. Hartig, T.A. Branchek, and R.L. Weinshank J. Biol. Chem. 267 1992 21098
7. Q.R. Liu, B. López-Corcuera, S. Mandiyan, H. Nelson, and N. Nelson J. Biol. Chem. 268 1993 2106
8. K.K. Madsen, H.S. White, and A. Schousboe Pharmacol. Ther. 125 2010 394
9. N.-H. Chen, M.A. Reith, and M. Quick Pflugers Arch. 447 2004 519
10. M. Palacín, R. Estevéz, J. Bertran, and Z. Antonio Physiol. Rev. 78 1998 969
11. Y. Zhou, S. Holmseth, C. Guo, B. Hassel, G. Höfner, H.S. Huitfeldt, K.T. Wanner, and N.C. Danbolt J. Biol. Chem. 287 2012 35733
12. Y. Zhou, S. Holmseth, R. Hua, A.C. Lehre, A.M. Olofsson, I. Poblete-Naredo, S.A. Kempson, and N.C. Danbolt Am. J. Physiol.-Renal Physiol. 302 2012 F316
13. L.A. Borden Neurochem. Int. 29 1996 335
14. G.A.R. Johnston, R.D. Allan, S.M.G. Kennedy, and B. Twitchin P. Krogsgaard-Larsen, J. Scheel-Krüger, H. Kofoed, GABA-Neurotransmitter: Pharmacochemical, Biochemical and Pharmacological Aspect 1978 Munksgaard Copenhagen 147 164
15. R.D. Myers L.L. Iversen, S.D. Iversen, S.H. Snyder, Handbook of Pharmacology 1975 Plenum New York 1 28
16. L.A. Borden, T.G.M. Dhar, K.E. Smith, R.L. Weinshank, T.A. Branchek, and C. Gluchowski Eur. J. Pharm. Mol. Pharmacol. Sect. 269 1994 219
17. S. Hog, J.R. Greenwood, K.B. Madsen, O.M. Larsson, B. Frolund, A. Schousboe, P. Krogsgaard-Larsen, and R.P. Clausen Curr. Top. Med. Chem. 6 2006 1861
18. A. Kragler, G. Höfner, and K.T. Wanner Eur. J. Med. Chem. 43 2008 2404
19. K.E. Andersen, C. Braestrup, F.C. Groenwald, A.S. Joergensen, E.B. Nielsen, U. Sonnewald, P.O. Soerensen, P.D. Suzdak, and L.J.S. Knutsen J. Med. Chem. 36 1993 1716
20. K.E. Andersen, M. Begtrup, M.S. Chorghade, E.C. Lee, J. Lau, B.F. Lundt, H. Petersen, P.O. Sørensen, and H. Thøgersen Tetrahedron 50 1994 8699
21. L.J.S. Knutsen, K.E. Andersen, J. Lau, B.F. Lundt, R.F. Henry, H.E. Morton, L. Nærum, H. Petersen, H. Stephensen, P.D. Suzdak, M.D.B. Swedberg, C. Thomsen, and P.O. Sørensen J. Med. Chem. 42 1999 3447
22. K.E. Andersen, J.L. Sørensen, P.O. Huusfeldt, L.J.S. Knutsen, J. Lau, B.F. Lundt, H. Petersen, P.D. Suzdak, and M.D.B. Swedberg J. Med. Chem. 42 1999 4281
23. K.E. Andersen, J.L. Sørensen, J. Lau, B.F. Lundt, H. Petersen, P.O. Huusfeldt, P.D. Suzdak, and M.D.B. Swedberg J. Med. Chem. 44 2001 2152
24. K.E. Andersen, J. Lau, B.F. Lundt, H. Petersen, P.O. Huusfeldt, P.D. Suzdak, and M.D.B. Swedberg Bioorg. Med. Chem. 9 2001 2773
25. H.-J. Böhm, D. Banner, S. Bendels, M. Kansy, B. Kuhn, K. Müller, U. Obst-Sander, and M. Stahl ChemBioChem 5 2004 637
26. L.A. Hardegger, B. Kuhn, B. Spinnler, L. Anselm, R. Ecabert, M. Stihle, B. Gsell, R. Thoma, J. Diez, J. Benz, J.-M. Plancher, G. Hartmann, D.W. Banner, W. Haap, and F. Diederich Angew. Chem., Int. Ed. 50 2011 314
27. C.M. Andersson, J. Larsson, and A. Hallberg J. Org. Chem. 55 1990 5757
28. M. Larhed, C.M. Andersson, and A. Hallberg Acta Chem. Scand. 47 1993 212
29. M. Larhed, C.M. Andersson, and A. Hallberg Tetrahedron 50 1994 285
30. P. Nilsson, M. Larhed, and A. Hallberg J. Am. Chem. Soc. 123 2001 8217
31. H. Neuvonen, K. Neuvonen, and P. Pasanen J. Org. Chem. 69 2004 3794
32. J.P. Kaplan, B.M. Raizon, M. Desarmenien, P. Feltz, P.M. Headley, P. Worms, K.G. Lloyd, and G. Bartholini J. Med. Chem. 23 1980 702
33. M. Krause, A. Rouleau, H. Stark, P. Luger, R. Lipp, M. Garbarg, J.C. Schwartz, and W. Schunack J. Med. Chem. 38 1995 4070
34. R. Martin Org. Prep. Proced. Int. 24 1992 369
35. G.W. Gribble, W.J. Kelly, and S.E. Emery Synthesis 1978 763
36. I.P. Beletskaya, and A.V. Cheprakov Chem. Rev. 100 2000 3009
37. E. Clot, C. Mégret, O. Eisenstein, and R.N. Perutz J. Am. Chem. Soc. 131 2009 7817
38. W.C. Still, M. Kahn, and A. Mitra J. Org. Chem. 43 1978 2923