Design and synthesis of 3-arylpyrrolidine-2-carboxamide derivatives as melanocortin-4 receptor ligands

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 6, 2008, Pages 1931-1938

  Tran, Joe A ^a   Tucci, Fabio C ^a   Arellano, Melissa ^a   Jiang, Wanlong ^a   Chen, Caroline W ^a   Marinkovic, Dragan ^a   Fleck, Beth A ^a   Wen, Jenny ^a   Foster, Alan C ^a   Chen, Chen ^a  

^a NEUROCRINE BIOSCIENCES INC   (United States)

Author keywords

Melanocortin 4 receptor; Pyrrolidine; Stereoisomer; Structure activity relationship; Synthesis

Indexed keywords

AMIDE; MELANOCORTIN 4 RECEPTOR; PYRROLIDINE DERIVATIVE;

ARTICLE; BINDING AFFINITY; CYCLIZATION; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION;

ADMINISTRATION, ORAL; ANIMALS; BIOLOGICAL AVAILABILITY; BRAIN; CYCLIZATION; DRUG DESIGN; MOLECULAR STRUCTURE; PYRROLIDINES; RATS; RECEPTOR, MELANOCORTIN, TYPE 4; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 40749144390     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.01.125     Document Type: Article

References (24)

1. Cone R.D. Nat. Neurosci. 8 (2005) 571
2. Yang Y.K. Obes. Rev. 4 (2003) 239
3. Scarlett J.M., and Marks D.L. Expert Opin. Investig. Drugs 14 (2005) 1233
4. Foster A.C., Chen C., Markison S., and Marks D.L. IDrugs 8 (2005) 314
5. Chaki S., and Okuyama S. Peptides 26 (2005) 1952
6. Chen C.W., Tran J.A., Jiang W., Tucci F.C., Arellano M., Wen J., Fleck B.A., Marinkovic D., White N.S., Pontillo J., Saunders J., Madan A., Foster A.C., and Chen C. Bioorg. Med. Chem. Lett. 16 (2006) 4800
7. Jiang W., Tucci F.C., Chen C.W., Arellano M., Tran J.A., White N.S., Marinkovic D., Pontillo J., Fleck B.A., Wen J., Saunders J., Madan A., Foster A.C., and Chen C. Bioorg. Med. Chem. Lett. 16 (2006) 4674
8. Tran J.A., Tucci F.C., Jiang W., Marinkovic D., Chen C.W., Arellano M., Markison S., Fleck B.A., Wen J., White N.S., Pontillo J., Saunders J., Marks D., Hoare S.R., Madan A., Foster A.C., and Chen C. Bioorg. Med. Chem. 15 (2007) 5166
9. Qi J., and Roush W.R. Org. Lett. 8 (2006) 2795
10. Jiang W., Chen C., Marinkovic D., Tran J.A., Chen C.W., Arellano L.M., White N.S., and Tucci F.C. J. Org. Chem. 70 (2005) 8924
11. Soloshonok V.A., Ueki H., Tiwari R., Cai C., and Hruby V.J. J. Org. Chem. 69 (2004) 4984
12. Haemers T., Wiesner J., Busson R., Jomaa H., and Van Calenbergh S. Eur. J. Org. Chem. 17 (2006) 3856
13. Chung J.Y.L., Wasicak J.T., Arnold W.A., May C.S., Nadzan A.M., and Holladay M.W. J. Org. Chem. 55 (1990) 270
14. CCDC 676318 (for trans-17-I) and CCDC 676319 (for cis-27-II) contain the supplementary crystallographic data for this paper. These data can be obtained via the CDCC website (www.ccdc.cam.ac.uk), or by contacting The Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK.
15. Williams R.M., Cao J., Tsujishima H., and Cox R.J. J. Am. Chem. Soc. 125 (2003) 12172
16. Yasuda N., Huffman M.A., Ho G.-J., Xavier L.C., Yang C., Emerson K.M., Tsay F.-R., Li Y., Kress M.H., Rieger D.L., Karady S., Sohar P., Abramson N.L., DeCamp A.E., Mathre D.J., Douglas A.W., Dolling U.-H., Grabowski E.J.J., and Reider P.J. J. Org. Chem. 63 (1998) 5438
17. Hydrogenation of 43a (Y = Cl) using the current conditions resulted in a de-chlorinated cis-44f as the major product. Therefore, 43a was reduced using sodium borohydride in the presence of nickel chloride.
18. Nickolls S.A., Cismowski M.I., Wang X., Wolff M., Conlon P.J., and Maki R.A. J. Pharmacol. Exp. Ther. 304 (2003) 1217
19. Pontillo J., Tran J.A., Makinson S., Joppa M., Fleck B.A., Marinkovic D., Arellano M., Tucci F.C., Lanier M., Nelson J., Saunders J., Hoare S.R., Foster A.C., and Chen C. Bioorg. Med. Chem. Lett. 15 (2005) 2541
20. Jiang W., Tran J.A., Tucci F.C., Fleck B.A., Hoare S.R., Markison S., Wen J., Chen C.W., Marinkovic D., Arellano M., Foster A.C., and Chen C. Bioorg. Med. Chem. Lett. 17 (2007) 6546
21. Mutulis F., Yahorava S., Mutule I., Yahorau A., Liepinsh E., Kopantshuk S., Veiksina S., Tars K., Belyakov S., Mishnev A., Rinken A., and Wikberg J.E. J. Med. Chem. 47 (2004) 4613
22. Chen C., Jiang W., Tucci F.C., Tran J.A., Fleck B.A., Hoare S.R., Joppa M., Markison S., Wen J., Sai Y., Johns M., Madan A., Chen T., Chen C.W., Marinkovic D., Arellano M., Saunders J., and Foster A.C. J. Med. Chem. 50 (2007) 5249
23. Chen C., Pontillo J., Fleck B.A., Gao Y., Wen J., Tran J.A., Tucci F.C., Marinkovic D., Foster A.C., and Saunders J. J. Med. Chem. 47 (2004) 6821
24. 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