Synthesis and evaluation of phenylcarbamate derivatives as ligands for nicotinic acetylcholine receptors

Bioorganic and Medicinal Chemistry

Volumn 12, Issue 18, 2004, Pages 4953-4962

  Gündisch, Daniela ^a   Andrä, Matthias ^a   Munoz, Lenka ^a   Cristina Tilotta, Maria ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

Epibatidine; MLA (methyllycaconitine); Nicotinic acetylcholine receptor; Phenylcarbamate

Indexed keywords

(3 BROMOPHENYL)CARBAMIC ACID 1 AZABICYCLO[2.2.2]OCT 3 YL ESTER; (3 BROMOPHENYL)CARBAMIC ACID 1 METHYLPIPERIDIN 2 YLMETHYL ESTER; (3 BROMOPHENYL)CARBAMIC ACID 1 METHYLPYRROLIDIN 2 YLMETHYL ESTER; (3 FLUOROPHENYL)CARBAMIC ACID 1 AZABICYCLO[2.2.2]OCT 3 YL ESTER; (3 FLUOROPHENYL)CARBAMIC ACID 1 METHYLPIPERIDIN 2 YLMETHYL ESTER; (3 FLUOROPHENYL)CARBAMIC ACID 1 METHYLPIPERIDIN 3 YL ESTER; (3 FLUOROPHENYL)CARBAMIC ACID 1 METHYLPYRROLIDIN 2 YLMETHYL ESTER; (3 METHYLPHENYL)CARBAMIC 1 METHYLPYRROLIDIN 2 YLMETHYL ESTER; (3 METHYLPHENYL)CARBAMIC ACID 1 METHYLPIPERIDIN 2 YLMETHYL ESTER; (3 TRIFLUOROMETHYLPHENYL)CARBAMIC ACID 1 AZABICYCLO[2.2.2]OCT 3 YL ESTER; (3 TRIFLUOROMETHYLPHENYL)CARBAMIC ACID 1 METHYLPIPERIDIN 2 YLMETHYL ESTER; (3 TRIFLUOROMETHYLPHENYL)CARBAMIC ACID 1 METHYLPIPERIDIN 3 YL ESTER; (3 TRIFLUOROMETHYLPHENYL)CARBAMIC ACID 1 METHYLPYRROLIDIN 2 YLMETHYL ESTER; 3 TOLYLCARBAMIC ACID 1 AZABICYCLO[2.2.2]OCT 3 YL ESTER; CARBAMIC ACID DERIVATIVE; NEUROPROTECTIVE AGENT; NICOTINIC RECEPTOR; PHENYLCARBAMIC ACID 1 AZABICYCLO[2.2.2]OCT 3 YL ESTER; PHENYLCARBAMIC ACID 1 METHYLPIPERIDIN 2 YLMETHYL ESTER; PHENYLCARBAMIC ACID 1 METHYLPIPERIDIN 3 YL ESTER; PHENYLCARBAMIC ACID 1 METHYLPYRROLIDIN 2 YLMETHYL ESTER; PIPERIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE; QUINUCLIDINE DERIVATIVE; RADIOLIGAND; RECEPTOR SUBTYPE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; BINDING ASSAY; DRUG BINDING; DRUG DETERMINATION; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ISOMERISM; STRUCTURE ANALYSIS;

ANIMALS; DRUG EVALUATION, PRECLINICAL; LIGANDS; PHENYLCARBAMATES; PROTEIN BINDING; RATS; RECEPTORS, NICOTINIC; SWINE; TORPEDO;

EID: 4444265797     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2004.06.041     Document Type: Article

References (38)

1. M.R. Picciotto, and M. Zoli J. Neurobiol. 53 2002 641
2. S. Jones, S. Sudweeks, and J.L. Yakel Trends Neurosci. 22 1999 555
3. R.C. Hogg, M. Raggenbass, and D. Bertrand Rev. Physiol. Biochem. Pharmacol. 147 2003 1
4. D. Bertrand, and J.P. Changeux Sem. The Neurosci. 7 1995 75
5. P.B. Sargent Annu. Rev. Neurosic. 16 1993 403
6. H. Wang, M. Yu, M. Ochani, C.A. Amella, M. Tanovic, S. Susarla, J.H. Li, H. Wang, H. Yang, L. Ulloa, Y. Al-Abed, C.J. Czura, and K.J. Tracey Nature 421 2003 384
7. M. Alkondon, E.F.R. Pereira, W.S. Cortes, A. Maelicke, and E. Albuquerque Eur. J. Neurosci. 9 1997 2734
8. A.A. Jensen, I. Mikkelsen, Frølund, H. Bräuner-Osborne, E. Falch, and P. Krogsgaard-Larsen Mol. Pharmacol. 64 2003 865
9. B. Søklide, I. Mikkelsen, T.B. Stensbøl, B. Andersen, S. Ebdrup, P. Krogsgaard-Larsen, and E. Falch Arch. Pharm. Pharm. Med. Chem. 329 1996 95
10. G. Villeneuve, D. Cécyre, H. Lejeune, M. Drouin, R. Lan, and R. Quirion Bioorg. Med. Chem. Lett. 13 2003 3847
11. R.R. Jonnala, J.H. Graham III, A.V. Terry Jr., J.W. Beach, J.A. Young, and J.J. Buccafusco Synapse 47 2003 262
12. M. Limbeck, and D. Gündisch J. Heterocycl. Chem. 40 2003 895
13. M. Andrä, C.M. Tilotta, and D. Gündisch Drugs Fut. 27 Suppl. A 2002 P113
14. B.G. Brown, and P. Hey Brit. J. Pharmacol. 11 1956 58
15. P. Hey Brit. J. Pharmacol. 7 1952 117
16. University of Kansas Research Foundation. U.S. Patent 863,197, 1959
17. Zielinsky, J.; Kenilworth, N. J. U.S. Patent 3,535,328, 1970; Chem. Abstr. 73, P 130899t
18. R. Simsek, J. Chang-Fong, M. Lee, M. Dukat, M.I. Damaj, B.R. Martin, and R.A. Glennon Bioorg. Med. Chem. Lett. 13 2003 2917
19. M.A. Abreo, N.-H. Lin, D.S. Garvey, D.E. Gunn, A.-M. Hettinger, J.T. Wasicak, P.A. Pavlik, Y.C. Martin, D.L. Donnelly-Roberts, D.J. Anderson, J.P. Sullivan, M. Williams, S.P. Arneric, and M.W. Holladay J. Med. Chem. 39 1996 817
20. L.G. Abood, and S. Grassi Biochem. Pharmacol. 35 1986 4199
21. J.S. Punzi, S. Banerejee, and L.G. Abood Biochem. Pharmacol. 41 1991 465
22. R. Naito, M. Takeuchi, K. Morihira, M. Hayakawa, K. Ikeda, T. Shibanuma, and Y. Isomura Chem. Pharm. Bull. (Tokyo) 46 1998 1286
23. W.W. Smith, L.F. Sancilio, J.B. Owera-Atepo, R.J. Naylor, and L. Lambert J. Pharm. Pharmacol. 40 1988 301
24. J. Lars, G. Nilsson, H. Sievertsson, R. Dahlbom, and B. Akerman J. Med. Chem. 14 1971 710
25. F. Gregan, J. Durinda, E. Racanska, and J. Zamocka Pharmazie 48 1993 465
26. Duschinsky, R. German Patent 931 653, 1955; Chem. Abstr. 49 P 1823d
27. Judd C. I. U.S. Patent 3,185,692, 1965; Chem. Abstr. 65 P 2275b
28. Macor, J.; Wu, E.; PCT Int Appl 2001; 35 (WO 97/30998); Chem. Abstr. 1997, 127, 1804p
29. G. Mullen, J. Napier, M. Balestra, T. DeCory, G. Hale, J. Macor, R. Mack, J. Loch III, E. Wu, A. Kover, P. Verhoest, A. Sampognaro, E. Phillips, Y. Zhu, R. Murray, R. Griffith, J. Blosser, D. Gurley, A. Machulskis, J. Zongrone, A. Rosen, and J. Gordon J. Med. Chem. 43 2000 4045
30. R. Hunt, and R.R. Renshaw J. Pharmacol. 35 1929 99
31. R.R. Renshaw, and W.D. Armstrong J. Biol. Chem. 103 1933 187
32. L.G. Abood, K. Shahid Salles, and A. Maiti Pharmacol. Biochem. Behav. 30 1988 403
33. M. Larhed, and A. Hallberg J. Org. Chem. 61 1996 9582
34. D. Gündisch, E.D. London, P. Terry, G.R. Hill, and A.G. Mukhin Neuroreport 10 1999 1631
35. H. Gohlke, D. Gündisch, S. Schwarz, G. Seitz, M.C. Tilotta, and T. Wegge J. Med. Chem. 45 2002 1064
36. A.G. Mukhin, D. Gündisch, A.G. Horti, A.O. Koren, G. Tamagnan, A.S. Kimes, J. Chambers, D.B. Vaupel, S. King, M.R. Picciotto, R. Innis, and E.D. London Mol. Pharmacol. 57 2000 642
37. R.L. Elliott, H. Kopecka, D.E. Gunn, N.-H. Lin, D.S. Garvey, K.B. Ryther, M. Holladay, D.J. Anderson, J.E. Campbell, J.P. Sullivan, M.J. Buckley, K.L. Gunther, A.B. O'Neill, M.W. Decker, and S.P. Arneric Bioorg. Med. Chem. Lett. 6 1996 2283
38. H.C. Brown, and S.K. Gupta J. Am. Chem. Soc. 94 1972 4370