Azetidine derivatives as novel γ-aminobutyric acid uptake inhibitors: Synthesis, biological evaluation, and structure-activity relationship

European Journal of Medicinal Chemistry

Volumn 45, Issue 6, 2010, Pages 2453-2466

  Faust, Mark R ^a   Höfner, Georg ^a   Pabel, Jörg ^a   Wanner, Klaus T ^a  

^a LUDWIG MAXIMILIANS UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

1 [2 [TRIS(4 METHOXYPHENYL)METHOXY]ETHYL]AZETIDINE 3 CARBOXYLIC ACID; 3 HYDROXY 3 (4 METHOXYPHENYL)AZETIDINE DERIVATIVE; 4 AMINOBUTYRIC ACID RECEPTOR BLOCKING AGENT; 4,4 BIS(3 METHYL 2 THIENYL)BUTENYL; 4,4 DIPHENYLBUTENYL; ACETIC ACID; AZETIDIN 2 YLACETIC ACID DERIVATIVE; AZETIDINE DERIVATIVE; BETA ALANINE; CARBOXYLIC ACID; PIPERIDINE; TETRAZOLE DERIVATIVE; TIAGABINE; UNCLASSIFIED DRUG;

4 AMINOBUTYRIC ACID UPTAKE; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; BIOLOGICAL ACTIVITY; DRUG POTENCY; DRUG SYNTHESIS; IC 50; LIPOPHILICITY; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ANIMALS; AZETIDINES; BIOLOGICAL TRANSPORT; CATTLE; GABA PLASMA MEMBRANE TRANSPORT PROTEINS; GAMMA-AMINOBUTYRIC ACID; INHIBITORY CONCENTRATION 50; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77950947883     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2010.02.029     Document Type: Article

References (56)

1. Lippa A.S., Coupet J., Greenblatt E.N., Klepner C.A., and Beer B. Pharmacol. Biochem. Behav. 11 (1979) 99-106
2. Chase T.N., Wexler N.S., and Barbeau A. Huntington's Disease (1979), Ravan Press, New York
3. Welch K.M., Chabi E., Bartosh K., Achar V.S., and Meyer J.S. Br. Med. J. 3 (1975) 516-517
4. Colello G.D., Hockenberry D.M., Bosmann H.B., Fuchs S., and Folkers K. Proc. Natl. Acad. Sci. U.S.A. 75 (1978) 6319-6323
5. Pilc A., and Lloyd K.G. Life Sci. 35 (1984) 2149-2154
6. Lloyd K.G., Morselli P.L., and Bartholin G. Med. Biol. 65 (1987) 159-165
7. Lloyd K.G., Thuret F., and Pilc A. J. Pharmacol. Exp. Ther. 235 (1985) 191-199
8. B Receptors in Mammalian Function (1990), Wiley, Chichester, United Kingdom 319-333
9. Lippert B., Metcalf B.W., June M.G., and Casara P. Eur. J. Biochem. 74 (1977) 441-445
10. Haigh J.R.M., and Feely M. Trends Pharmacol. Sci. 9 (1988) 361-366
11. Schmidt D. Benzodiazepines: diazepam. In: Levy R.H., Mattson R.H., and Meldrum B.S. (Eds). Antiepileptic Drugs. fourth ed. (1995), Raven Press, New York 705-724
12. Schousbou A., and Kanner B.I. GABA transporters: functional and pharmacological properties. In: Egebjerg J., Schouboe A., and Krogsgaard-Larsen P. (Eds). Glutamate and GABA Receptors and Transporters: Structure, Function and Pharmacology (2002), Francis & Taylor, London 337-349
13. Miller J.W., Kleven D.T., Domin B.A., and Fremau R.T. In: Reith M.E.A. (Ed). Neurotransmitter Transporters: Structure, Function, and Regulation (1997), Humana Press, Totowa 101-150
14. Amara S.G., and Kuhar M.J. Annu. Rev. Neurosci. 16 (1993) 73-93
15. Kanner B.I. J. Exp. Biol. 196 (1994) 237-249
16. Nelson N. J. Neurochem. 71 (1998) 1785-1803
17. Yamashita A., Singh S.K., Kawate T., Jin Y., and Gouaux E. Nature 473 (2005) 215-223
18. Wein T., and Wanner K.T. J. Mol. Model. 16 (2010) 155-161
19. Pallo A., Bencsura A., Heja L., Beke T., Perczel A., Kardos J., and Simon A. Biochem. Biophys. Res. Commun. 364 (2007) 952-958
20. Borden L.A., Smith K.E., Gustafson E.L., Branchek T.A., and Weinshank R.L. J. Neurochem. 64 (1995) 977-984
21. Borden L.A., Dhar M.T.G., Smith K.E., Weinshank R.L., Branchek A.T., and Gluchowski C. Eur. J. Pharmacol. Mol. Pharmacol. 269 (1994) 219-224
22. Christiansen B., Meinild A.-K., Jensen A.A., and Bräuner-Osborne H. J. Biol. Chem. 282 (2007) 19331-19341
23. Johnston G., Krogsgaard-Larsen P., and Stephenson A. Nature 258 (1975) 627-628
24. Tamura S., Nelson H., Tamura A., and Nelson N. J. Biol. Chem. 270 (1995) 28712-28715
25. Croucher M.J., Meldrum B.S., and Krogsgaard-Larsen P. Eur. J. Pharmacol. 89 (1983) 217-228
26. Ali F.E., Bondinell W.E., Dandridge P.A., Frazee J.S., Garvey W., Girard G.R., Kaiser C., Ku T.W., Lafferty J.J., Moonsammy G.I., Oh H.-J., Rush J.A., Setler P.E., Stringer O.D., Venslavsky J.W., Volpe B.W., Yunger L.M., and Zirkle C.L. J. Med. Chem. 28 (1985) 653-660
27. Krogsgaard-Larsen P., Frølund B., and Frydenvang K. Curr. Pharm. Des. 6 (2000) 1193-1209
28. Dalby N.O. Neuropharmacology 39 (2000) 2399-2407
29. Yunger L.M., Fowler P.J., Zarevics P., and Setler P.E. J. Pharmacol. Exp. Ther. 228 (1984) 109-115
30. Nielsen E.B., Suzdak P.D., Andersen K.E., Knutsen L.J., Sonnewald U., and Braestrup C. Eur. J. Pharmacol. 196 (1991) 257-266
31. Swinyard E.A., White H.S., Wolf H.H., and Bondinell W.E. Epilepsia 32 (1991) 569-577
32. Dalby N.O., Thomsen C., Fink-Jensen A., Lundbeck J., Søkilde B., Man C.M., Sørensen P.O., and Meldrum B. Epilepsy Res. 28 (1997) 51-61
33. Morimoto K., Sato H., Yamamoto Y., Watanabe T., and Suwaki H. Epilepsia 38 (1997) 966-974
34. Genton P., Guerrini R., and Perucca E. Epilepsia 42 (2001) 42-45
35. Fülep G.H., Hoesl C.E., Höfner G., and Wanner K.T. Eur. J. Med. Chem. 41 (2006) 809-824
36. G. Hoefner, G. Fuelep, K.T. Wanner, WO0014060, 2000.
37. Dhar T., Borden L., Smith K., Branchek T., Weinshank R., and Gluchowski C. J. Med. Chem. 37 (1994) 2334-2342
38. Thomsen C., Sørensen P., and Egebjerg J. Br. J. Pharmacol. 120 (1997) 983-985
39. Anderson A.G., and Lok R. J. Org. Chem. 37 (1972) 3953-3955
40. Carruthers N., Wong S.-C., and Chan T.-M. J. Chem. Res. Synop. 9 (1996) 430-431
41. P. Barth, H. Fritschi, J.-E. Nystroem, J.-E.; Pfenninger, A. WO9702241, 1997.
42. S.J. Woodhead, R. Downham, C. Hamlett, S. Howard, H.F. Sore, M.L. Verdonk, D.W. Walker, R.W.A. Luke, WO2006136830, 2006.
43. A.F. Orr, Shell Oil Company, US Patent No. 4,620,866, 1986, 1-8.
44. Shono T., Matsumura Y., Uchida K., and Nakatani F. Bull. Chem. Soc. Jpn. 61 (1988) 3029-3031
45. Morimoto A., Okutani T., and Masuda K. Chem. Pharm. Bull. 21 (1973) 228-231
46. Katrizky A.R., Cundy D.J., and Chen J. J. Heterocycl. Chem. 31 (1994) 271-275
47. Satoh Y., and Marcopulos N. Tetrahedron Lett. 36 (1995) 1759-1762
48. Pearlman W.M. Tetrahedron Lett. 8 (1967) 1663-1664
49. Miller R.A., Lang F., Marcune B., Zewge D., Song Z.J., and Karady S. Synth. Commun. 33 (2003) 3347-3353
50. E. Castiglioni, R. Di Fabio, M. Gianotti, M. Mesic, F. Pavone, S. Rast, L.P. Stasi, WO2009016084, 2009.
51. McGrath M.E., Sprengeler P.A., Hirschbein B., Somoza J.R., Lehoux I., Janc J.W., Gjerstad E., Graupe M., Estiarte A., Venkataramani C., Liu Y., Yee R., Ho R.D., Green M.J., Lee Ch.S., Liu L., Tai V., Spencer J., Sperandio D., and Katz B.A. Biochemistry 45 (2006) 5964-5973
52. Nudelman A., Bechor Y., Falb E., Fischer B., Wexler B.A., and Nudelman A. Synth. Commun. 28 (1998) 471-474
53. Faust M.R., Hoesl C.E., and Wanner K.T. Heterocycles 75 (2008) 2981-2988
54. Dodd P.R., Hardy J.A., Oakley A.E., Edwardson J.A., Perry E.K., and Delaunoy J.-P. Brain Res. 226 (1981) 107-118
55. Höfner G., and Wanner K.T. Neurosci. Lett. 364 (2004) 53-57
56. Bradford M. Anal. Biochem. 72 (1976) 248-254