1-Amino-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid as a Tic mimetic: Application in the synthesis of potent human melanocortin-4 receptor selective agonists

Bioorganic and Medicinal Chemistry Letters

Volumn 15, Issue 14, 2005, Pages 3430-3433

  Bakshi, Raman K ^a   Hong, Qingmei ^a   Olson, J T ^a   Ye, Zhixiong ^a   Sebhat, Iyassue K ^a   Weinberg, David H ^a   MacNeil, Tanya ^a   Kalyani, Rubana N ^a   Tang, Rui ^a   Martin, William J ^a   Strack, Alison ^a   McGowan, Erin ^a   Tamvakopoulos, Constantin ^a   Miller, Randy R ^a   Stearns, Ralph A ^a   Tang, Wei ^a   Maclntyre, D Euan ^a   Van Der Ploeg, Lex H T ^a   Patchett, Arthur A ^a   Nargund, Ravi P ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

MC 4 agonist; Obesity; Tic

Indexed keywords

1 AMINO 1,2,3,4 TETRAHYDRONAPHTHALENE 2 CARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE; MELANOCORTIN 4 RECEPTOR; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DIASTEREOISOMER; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; RAT;

CARBOXYLIC ACIDS; HUMANS; MOLECULAR CONFORMATION; MOLECULAR MIMICRY; PROTEIN BINDING; RECEPTOR, MELANOCORTIN, TYPE 4; STRUCTURE-ACTIVITY RELATIONSHIP; TETRAHYDROISOQUINOLINES; TETRAHYDRONAPHTHALENES;

EID: 20644455122     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2005.05.012     Document Type: Article

References (21)

1. For recent reviews on melanocortin systems, see S. Chaki, and A. Nakazato Drug Future 29 2004 1065
2. M.A. Bednarek, and T.M. Fong Expert Opin. Ther. Patents 14 2004 1
3. A. Catania, S. Gatti, G. Colombo, and J.M. Lipton Pharmacol. Rev. 56 2004 1
4. I. Sebhat, Z. Ye, M. Bednarek, D. Weinberg, R. Nargund, and T.M. Fong Annu. Rep. Med. Chem. 38 2003 31
5. I. Gantz, and T.M. Fong Ann. J. Physiol. Endocrinol. Metab. 284 2003 E468
6. J.D. Speak, and M.J. Bishop Expert Opin. Ther. Patents 12 2002 1613
7. J.E.S. Wikberg Expert Opin. Ther. 11 2001 61
8. D. Lu, D. Willard, I.R. Patel, S. Kadwell, L. Overton, T. Kost, M. Luther, W. Chen, R.P. Woychik, W.O. Wilkison, and R.D. Cone Nature 371 1994 799
9. S.J. Bultman, E.J. Michaud, and R.P. Woychik Cell 71 1992 1195
10. W. Fan, B.A. Boston, R.A. Kesterson, V.J. Hruby, and R.D. Cone Nature 385 1997 165
11. I.K. Sebhat, W.J. Martin, Y. Zhixiong, K. Barakat, R.T. Mosley, D.B.R. Johnston, R.K. Bakshi, B. Palucki, D.H. Weinberg, T. MacNeil, R.N. Kalyani, R. Tang, R.A. Stearns, R.R. Miller, 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. Ploeg, A.A. Patchett, and R.P. Nargund J. Med. Chem. 45 2002 4589
12. Tic mimic 2 design is based on disconnection shown below
13. E.J. Miriconi, and P.H. Mazzocchi J. Org. Chem. 31 1966 1372
14. D.R. Buckle, C.S.V. Hough-Frydrych, I.L. Pinto, D.G. Smith, and J.M. Tedder J. Chem. Soc., Perkin Trans. 1 1991 63
15. D.L. Finn, R.E. Zella, and P.A. Grieco J. Org. Chem. 48 1983 2424
16. For detail protocol of assay, see M.A. Bednarek, T. MacNeil, R.N. Kalyani, R. Tang, L.H.T. Van der Ploeg, and D.H. Weinberg J. Med. Chem. 44 2001 3665
17. Absolute stereochemistry was established by X-ray of boc intermediate
18. Strack, A. M., et al. Unpublished results. Details will be published separately
19. W.J. Martin, E. McGowan, D.E. Cashen, L.T. Gantert, J.E. Drisko, G.J. Hom, R. Nargund, I. Sebhat, A.D. Howard, L.H.T. Van der Ploeg, and D.E. MacIntyre Eur. J. Pharmacol. 454 2002 71
20. L.H.T. Van der Ploeg, W.J. Martin, A.D. Howard, R.P. Nargund, C.P. Austin, X. Guan, J. Drisko, D. Cashen, I. Sebhat, A.A. Patchett, D.J. Figueroa, A.G. DiLella, D.H. Connolly, D.H. Weinberg, C.T. Tan, O.C. Palyha, S. Pong, T. MacNeil, C. Rosenblum, A. Vongs, M. Tota, R.S. Chang, R. Stearns, C. Tamvakopoulos, G. Christ, D.L. Drazen, D.L. Spar, R.J. Nelson, and D.E. MacIntyre Proc. Natl. Acad. Sci. U.S.A. 99 2002 11381
21. Stearns, R. A., et al. Unpublished results. Details will be published separately