Structure-activity relationships of N-substituted ligands for the α7 nicotinic acetylcholine receptor

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 1, 2010, Pages 104-107

  Mortell, Kathleen H ^a   Schrimpf, Michael R ^a   Bunnelle, William H ^a   Anderson, David J ^a   Gronlien, Jens Halvard ^a   Hagene, Kirsten Thorin ^a   Gopalakrishnan, Murali ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

Epibatidine; Neuronal nicotinic receptors; Neuroscience; Nicotine; Nicotinic acetylcholine receptors; Nicotinic agonist

Indexed keywords

2 (6 PHENYLPYRIDAZIN 3 YL) 5 (PYRIDIN 3 YLMETHYL)OCTAHYDROPYRROLO[3,4 C]PYRROLE; A 582941; BUNGAROTOXIN RECEPTOR; EPIBATIDINE; NICOTINIC AGENT; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG DESIGN; DRUG EFFICACY; DRUG IDENTIFICATION; DRUG POTENCY; DRUG STRUCTURE; NONHUMAN; RAT; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

ANIMALS; HUMANS; LIGANDS; NICOTINIC AGONISTS; OOCYTES; PYRIDAZINES; PYRROLES; RECEPTORS, NICOTINIC; STRUCTURE-ACTIVITY RELATIONSHIP; XENOPUS;

EID: 72049099297     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.11.023     Document Type: Article

References (27)

1. D'hoedt D., and Bertrand D. Exp. Opin. Ther. Targets 13 (2009) 395
2. Jensen A.A., Frolund B., Liljefors T., and Krogsgaard-Larsen P. J. Med. Chem. 48 (2005) 4705
3. Broad L.M., Sher E., Astles P.C., Zwart R., and O'Neill M.J. Drugs Future 32 (2007) 161
4. Mullen G., Napier J., Balestra M., DeCory T., Hale G., Macor J., Mack R., Loch J., Wu E., Kover A., Verhoest P., Sampognaro A., Phillips E., Zhu Y., Murray R., Griffith R., Blosser J., Gurley D., Machulskis A., Zongrone J., Rosen A., and Gordon J. J. Med. Chem. 43 (2000) 4045
5. Bodnar A.L., Cortes-Burgos L.A., Cook K.K., Dinh D.M., Groppi V.E., Hajos M., Higdon N.R., Hoffmann W.E., Hurst R.S., Myers J.K., Rogers B.N., Wall T.M., Wolfe M.L., and Wong E. J. Med. Chem. 48 (2005) 905
6. Wishka D.G., Walker D.P., Yates K.M., Reitz S.C., Jia S., Myers J.K., Olson K.L., Jacobsen E.J., Wolfe M.L., Groppi V.E., Hanchar A.J., Thornburgh B.A., Cortes-Burgos L.A., Wong E.H.F., Staton B.A., Raub T.J., Higdon N.R., Wall T.M., Hurst R.S., Walters R.R., Hoffmann W.E., Hajos M., Franklin S., Carey G., Gold L.H., Cook K.K., Sands S.B., Zhao S.X., Soglia J.R., Kalgutkar A.S., Arneric S.P., and Rogers B.N. J. Med. Chem. 49 (2006) 4425
7. Tatsumi R., Fujio M., Takanashi S.-I., Numata A., Katayama J., Satoh H., Shiigi Y., Maeda J.-I., Kuriyama M., Horikawa T., Murozono T., Hashimoto K., and Tanaka H. J. Med. Chem. 49 (2006) 4374
8. Hu M., Waring J.F., Gopalakrishnan M., and Li J. J. Neurochem. 106 (2008) 1371
9. Sullivan J.P., Briggs C.A., Donnelly-Roberts D., Brioni J.D., Radek R.J., McKenna D.G., Campbell J.E., Arneric S.P., Decker M.W., and Bannon A.W. Med. Chem. Res. 4 (1994) 502
10. Tietje K.R., Anderson D.J., Bitner R.S., Blomme E.A., Brackemeyer P.J., Briggs C.A., Browman K.E., Bury D., Curzon P., Drescher K.U., Frost J.M., Fryer R.M., Fox G.B., Gronlien J.H., Hakerud M., Gubbins E.J., Halm S., Harris R., Helfrich R.J., Kohlhaas K.L., Law D., Malysz J., Marsh K.C., Martin R.L., Meyer M.D., Molesky A.L., Nikkel A.L., Otte S., Pan L., Puttfarcken P.S., Radek R.J., Robb H.M., Spies E., Thorin-Hagene K., Waring J.F., Ween H., Xu H., Gopalakrishnan M., and Bunnelle W.H. CNS Neurosci. Ther. 14 (2008) 65
11. Bitner R.S., Bunnelle W.H., Anderson D.J., Briggs C.A., Buccafusco J., Curzon P., Decker M.W., Frost J.M., Gronlien J.H., Gubbins E., Li J., Malysz J., Markosyan S., Marsh K., Meyer M.D., Nikkel A.L., Radek R.J., Robb H.M., Timmermann D., Sullivan J.P., and Gopalakrishnan M. J. Neurosci. 27 (2007) 10578
12. Bunnelle, W. H.; Tietje, K. R.; Frost, J. M.; Peters, D.; Ji, J.; Li, T.; Scanio, M. J. C.; Shi, L.; Anderson, D. J.; Dyhring, T.; Grønlien, J. H.; Ween, H.; Thorin-Hagene, K.; Meyer, M. D. J. Med. Chem., in press.
13. Cashin A.L., Petersson E.J., Lester H.A., and Dougherty D.A. J. Am. Chem. Soc. 127 (2005) 350
14. Basha, A.; Bunnelle, W. H.; Dart, M. J.; Gallagher, M. E.; Ji, J.; Li, T.; Pace, J. M.; Ryther, K. B.; Tietje, K. R. U.S. 7,399765 B2.
15. 3H]-cytisine from rat brain homogenate:. Pabreza L.M., Dhawan S., and Kellar K.J. Mol. Pharmacol. 39 (1990) 9
16. Anderson D.J., Bunnelle W.H., Surber B., Du J., Surowy C., Tribollet E., Marguerat A., Bertrand D., and Gopalakrishnan M. J. Pharmacol. Exp. Ther. 324 (2008) 179
17. Tsuge O., Kanemasa S., Ohe M., Yorozu K., Takenaka S., and Ueno K. Bull. Chem. Soc. Jpn. 60 (1987) 4067
18. Lubineau A., Bouchain G., and Queneau Y. J. Chem. Soc., PT1 19 (1995) 2433
19. The assignment was made by conversion to 12. The cis relative stereochemistry of 12 was established by 2D NMR and is consistent with literature.
20. Briggs C.A., Schrimpf M.R., Anderson D.J., Gubbins E.J., Gronlien J.H., Hakerud M., Ween H., Thorin-Hagene K., Malysz J., Li J., Bunnelle W.H., Gopalakrishnan M., and Meyer M.D. Br. J. Pharmacol. 153 (2008) 1054
21. Carroll F.I. Bioorg. Med. Chem. Lett. 14 (2004) 1889
22. Barlocco D., Cignarella G., Tondi D., Vianello P., Villa S., Bartolini A., Ghelardini C., Nicoletta G., Anderson D.J., Kuntzweiler T.A., Colombo D., and Toma L. J. Med. Chem. 41 (1998) 674
23. Wei Z.-L., Xiao Y., Kellar K.J., and Kozikowski A.P. Bioorg. Med. Chem. Lett. 14 (2004) 1855
24. Macor J.E., Gurley D., Lanthorn G., Loch J., Mack R.A., Mullen G., Tran O., Wright N., and Gordon J.C. Bioorg. Med. Chem. Lett. 11 (2001)
25. Biton B., Bergis O.E., Galli F., Nedelec A., Lochead A.S., Jegham S., Godet D., Lanneau C., Santamaria R., Chesney F., Leonardon J., Granger P., Debono M.W., Bohme G.A., Sgard F., Besnard F., Graham D., Coste A., Oblin A., Curet O., Vige X., Voltz C., Rouquier L., Souilhac J., Santucci V., Gueudet C., Francon D., Steinberg R., Griebel G., Oury-Donat F., George P., Avenet P., and Scatton B. Neuropsychopharmacology 32 (2007) 1
26. Papke R.L., Meyer E.M., Lavieri S., Bollampally S.R., Papke T.A.S., Horenstein N.A., Itoh Y., and Porter Papke J.K. Neuropharmacology 46 (2004) 1023
27. Mazurov A., Klucik J., Miao L., Phillips T.Y., Seamans A., Schmitt J.D., Hauser T.A., Johnson R.T., and Miller C. Bioorg. Med. Chem. Lett. 15 (2005) 2073