Privileged structure-based ligands for melanocortin receptors - Tetrahydroquinolines, indoles, and aminotetralines

Bioorganic and Medicinal Chemistry Letters

Volumn 15, Issue 20, 2005, Pages 4459-4462

  Fisher, Matthew J ^a   Backer, Ryan T ^a   Husain, Saba ^a   Hsiung, Hansen M ^a   Mullaney, Jeffrey T ^a   O'Brian, Thomas P ^a   Ornstein, Paul L ^a   Rothhaar, Roger R ^a   Zgombick, John M ^a   Briner, Karin ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

Melanocortin receptors; Privileged structures

Indexed keywords

HETEROCYCLIC COMPOUND; INDOLE DERIVATIVE; LIGAND; MELANOCORTIN 4 RECEPTOR; MELANOCORTIN RECEPTOR; QUINOLINE DERIVATIVE; SULFONAMIDE; TETRALIN DERIVATIVE;

ARTICLE; DRUG ACTIVITY; DRUG STRUCTURE; STRUCTURE ACTIVITY RELATION;

HUMANS; INDOLES; LIGANDS; MOLECULAR STRUCTURE; QUINOLINES; RECEPTORS, MELANOCORTIN; TETRAHYDRONAPHTHALENES;

EID: 24344485148     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2005.07.035     Document Type: Article

References (22)

1. F.L. Strand Ann. N.Y. Acad. Sci. 897 1999 1
2. P.E. Smith Science 44 1916 280
3. R.D. Cone, K.G. Mounthoy, L.S. Robbins, J.H. Nadu, K.R. Johnson, L. Roselli-Rehfuss, and M.T. Mortund Ann. N.Y. Acad. Sci. 680 1993 342
4. For examples of efforts directed at the preparation of selective ligands see: K. Pan, M.K. Scott, D.H.S. Lee, L.J. Fitzpatrick, J.J. Crooke, R.A. Rivero, D.I. Rosenthal, A.H. Vaidya, B. Zhao, and A.B. Reita Biorg. Med. Chem. Lett. 11 2003 185
5. I.K. Sebhat, W.J. Martin, S. Ye, K. Marakat, R.T. Mosley, D.B.R. Johnston, R. Bakshi, B. Palucki, D.H. Weinberg, T. MacNeil, R.N. Kalyani, R. Tang, R.A. Sterns, C. Tamvakopoulos, A.M. Strack, E. McGowan, D.E. Cashen, J.E. Drisko, G.J. Hom, A.D. Howard, D.E. MacIntyre, L.H.T. van der Ploeg, A.A. Patchett, and R.P. Nargund J. Med. Chem. 45 2002 4589
6. B. Dyck, J. Parfker, T. Phillips, L. Carter, B. Murphy, R. Summers, J. Hermann, T. Baker, M. Cismowski, J. Saunders, and V. Goodfellow Biorg. Med. Chem. Lett. 13 2003 3793
7. J. Jhang, C. Xiong, J. Ying, W. Wamg, and V.J. Hrubt Org. Lett. 5 2003 3115
8. C. Fotsch, D.M. Smith, J.A. Adams, J. Cheetham, M. Croghan, E.M. Dorhety, C. Hale, M.A. Jarosinski, M.G. Kelly, M.H. Norman, N.A. Tamayo, N. Xi, and J.W. Baumgartner Biorg. Med. Chem. Lett. 13 2003 2337
9. T.I. Richardson, P.L. Ornstein, K. Briner, M.J. Fisher, R.T. Backer, C.K. Biggers, M.P. Clay, P.J. Emmerson, L.W. Hertel, H.M. Hsiung, S. Husain, S.D. Kahl, J.A. Lee, T.D. Lindstrom, M.J. Martinelli, J.P. Mayer, J.T. Mullaney, T.P. O'Brien, J.M. Pawlak, K.D. Revell, J. Shah, and J.M. Zgombick J. Med. Chem. 47 2004 744
10. B.E. Evans, K.E. Rittle, M.G. Bock, R.M. DiPardo, R.M. Freidinger, W.L. Whitter, G.F. Lundell, D.F. Veber, P.S. Anderson, R.S.L. Chang, V.J. Lotti, D.J. Cerino, T.B. Chen, P.J. Kling, K.A. Kunkel, J.P. Springer, and J. Hirshfield J. Med. Chem. 31 1988 2235
11. For examples of this phenomenon, compare the ligands for growth hormone secretagogues outlined in the following papers: A.A. Patchett, R.P. Nargund, J.R. Tata, M.-H. Chen, K.J. Barakat, D.B.R. Johnston, K. Cheng, W.W.-S. Chan, and B. Butler Proc. Natl. Acad. Sci. U.S.A. 79 1995 7001
12. D.E. Seyler, J.A. Dodge, J.J. Osborne, K.L. Cox, D. Viswanath, A.F. Wilmot, M.J. Keaton, M.L. Heiman, and H.U. Bryant Drug Dev. Res. 49 2000 260
13. J.T. MacAndrew, S.S. Ellery, M.A. Parry, L.C. Pan, and S.C. Black Eur. J. Pharmacol. 432 2001 195
14. K. Bondensgaard, M. Ankersen, H. Thogersen, B.S. Hansen, B.S. Wulff, and R.P. Bywater J. Med. Chem. 47 2004 488
15. W.D. Brown, and A-H. Gouliaev Synthesis 2002 83
16. J.P. Wolfe, and S.L. Buchwald J. Org. Chem. 65 2000 1144
17. A.G. Romero, J.A. Leiby, R.B. McCall, M.F. Piercey, M.W. Smith, and F. Han J. Med. Chem. 36 1993 2066
18. A. Speicher, T. Klaus, and T. Eicher J. Prakt. Chem./Chem-Ztg 340 1998 581
19. The details of the binding assay have been recently described. See Ref. 5.
20. Functional activity was determined by measuring the cAMP release with a standard luciferase assay employing HEK 293 cells stably transfected with hMC4 (data not shown). Compounds of this paper were agonists with relative efficacies 60-100% of the maximum response obtained with NDP-α-MSH.
21. Each data point represents the average of at least two determinations with an average error of the binding assay being 15%.
22. Boninell, W.E.; Neeb, M.J. WO 02/05819, 2002; Chem. Abstr. 2002, 136, 134783.