Synthesis and characterization of trans-4-(4-chlorophenyl)pyrrolidine-3-carboxamides of piperazinecyclohexanes as ligands for the melanocortin-4 receptor

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 24, 2007, Pages 6825-6831

  Chen, Caroline W ^a   Tran, Joe A ^a   Fleck, Beth A ^a   Tucci, Fabio C ^a   Jiang, Wanlong ^a   Chen, Chen ^a  

^a NEUROCRINE BIOSCIENCES INC   (United States)

Author keywords

Agonist; Antagonist; Melanocortin 4 receptor; Pyrrolidine; Structure activity relationship; Synthesis

Indexed keywords

3 FLUORO 4 METHOXYCARBOXAMIDE DERIVATIVE; 4 (4 CHLOROPHENYL)PYRROLIDINE 3 CARBOXAMIDE DERIVATIVE; AMIDE; CYCLOHEXANE; MELANOCORTIN 4 RECEPTOR; MELANOCORTIN 4 RECEPTOR AGONIST; PIPERAZINECYCLOHEXANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CACHEXIA; DRUG BINDING; DRUG POTENCY; DRUG SYNTHESIS; FEEDING BEHAVIOR; HORMONE RECEPTOR INTERACTION; LIGAND BINDING; NONHUMAN; OBESITY;

AMIDES; CARBOXYLIC ACIDS; CHLORINE COMPOUNDS; CYCLOHEXANES; LIGANDS; MOLECULAR STRUCTURE; PIPERAZINES; PYRROLIDINES; RECEPTOR, MELANOCORTIN, TYPE 4; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 35848963836     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.10.032     Document Type: Article

References (16)

1. Cone R.D. Nat. Neurosci. 8 (2005) 571
2. Yang Y.K. Obes. Rev. 4 (2003) 239
3. For recent review articles, see:. Nargund R.P., Strack A.M., and Fong T.M. J. Med. Chem. 49 (2006) 4035
4. Chen C. Prog. Med. Chem. 45 (2007) 111
5. Scarlett J.M., and Marks D.L. Expert Opin. Investig. Drugs 14 (2005) 1233
6. Foster A.C., Chen C., Markison S., and Marks D.L. IDrugs 8 (2005) 314
7. Ujjainwalla, F. 230th ACS National Meeting, Washington, DC, USA, 2005; MEDI 275.
8. Sebhat I.K., Martin W.J., Ye Z., Barakat K., Mosley R.T., Johnston D.B., Bakshi R., Palucki B., Weinberg D.H., MacNeil T., Kalyani R.N., Tang R., Stearns R.A., Miller R.R., Tamvakopoulos C., Strack A.M., McGowan E., Cashen D.E., Drisko J.E., Hom G.J., Howard A.D., MacIntyre D.E., van der Ploeg L.H., Patchett A.A., and Nargund R.P. J. Med. Chem. 45 (2002) 4589
9. Tran J.A., Tucci F.C., Chen C.W., Jiang W., Marinkovic D., Arellano M., Fleck B.A., and Chen C. Bioorg. Med. Chem. Lett. 17 (2007) 5165
10. Pontillo J., Tran J.A., White N.S., Arellano M., Fleck B.A., Marinkovic D., Tucci F.C., Saunders J., Foster A.C., and Chen C. Bioorg. Med. Chem. Lett. 15 (2005) 5237
11. Tran J.A., Pontillo J., Arellano M., Fleck B.A., Tucci F.C., Marinkovic D., Chen C.W., Saunders J., Foster A.C., and Chen C. Bioorg. Med. Chem. Lett. 15 (2005) 3434
12. Nickolls S.A., Cismowski M.I., Wang X., Wolff M., Conlon P.J., and Maki R.A. J. Pharmacol. Exp. Ther. 304 (2003) 1217
13. Dyck B., Parker J., Phillips T., Carter L., Murphy B., Summers R., Hermann J., Baker T., Cismowski M., Saunders J., and Goodfellow V. Bioorg. Med. Chem. Lett. 13 (2003) 3793
14. Richardson T.I., Ornstein P.L., Briner K., Fisher M.J., Backer R.T., Biggers C.K., Clay M.P., Emmerson P.J., Hertel L.W., Hsiung H.M., Husain S., Kahl S.D., Lee J.A., Lindstrom T.D., Martinelli M.J., Mayer J.P., Mullaney J.T., O'Brien T.P., Pawlak J.M., Revell K.D., Shah J., Zgombick J.M., Herr R.J., Melekhov A., Sampson P.B., and King C.H. J. Med. Chem. 47 (2004) 744
15. Yang Y.K., Fong T.M., Dickinson C.J., Mao C., Li J.Y., Tota M.R., Mosley R., Van Der Ploeg L.H., and Gantz I. Biochemistry 39 (2000) 14900
16. Fleck B.A., Chen C., Yang W., Huntley R., Markison S., Nickolls S.A., Foster A.C., and Hoare S.R. Biochemistry 44 (2005) 14494