Design and synthesis of noncompetitive metabotropic glutamate receptor subtype 5 antagonists

Bioorganic and Medicinal Chemistry Letters

Volumn 16, Issue 13, 2006, Pages 3371-3375

  Kulkarni, Santosh S ^a   Nightingale, Barbara ^a   Dersch, Christina M ^a   Rothman, Richard B ^a   Newman, Amy Hauck ^a  

^a NATIONAL INSTITUTE ON DRUG ABUSE   (United States)

Author keywords

Metabotropic glutamate receptor subtype 5; mGluR5; Noncompetitive antagonists

Indexed keywords

METABOTROPIC RECEPTOR 5; METABOTROPIC RECEPTOR 5 ANTAGONIST; METABOTROPIC RECEPTOR AGONIST; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; DRUG BINDING; DRUG DESIGN; DRUG SYNTHESIS; PHARMACOPHORE;

AMIDES; ANIMALS; BINDING SITES; CATTLE; CRYSTALLOGRAPHY, X-RAY; DRUG DESIGN; DRUG EVALUATION, PRECLINICAL; LIGANDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; RECEPTORS, METABOTROPIC GLUTAMATE; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33646923402     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.04.032     Document Type: Article

References (25)

1. Conn P.J., and Pin J.P. Annu. Rev. Pharmacol. Toxicol. 37 (1997) 205
2. Spooren W.P.J.M., Gasparini F., Salt T.E., and Kuhn R. Trends Pharmacol. Sci. 22 (2001) 331
3. Swanson C.J., Bures M., Johnson M.P., Linden A.M., Monn J.A., and Schoepp D.D. Nat. Rev. Drug Discov. 4 (2005) 131
4. Chiamulera C., Eping-Jordon M.P., Zocchi A., Marcon C., Cottiny C., Tacconi S., Corsi M., Orzi F., and Conquet F. Nat. Neurosci. 4 (2001) 873
5. Popik P., and Wrobel M. Neuropharmacology 43 (2002) 1210
6. Paterson N.E., Semenova S., Gasparini F., and Markou A. Psychopharmacology (Berl.) 167 (2003) 257
7. Backstrom P., Bachteler D., Koch S., Hyytia P., and Spanagel R. Neuropsychopharmacology 29 (2004) 921
8. Varney M.A., Cosford N.D., Jachec C., Rao S.P., Sacaan A., Lin F.F., Bleicher L., Santori E.M., Flor P.J., Allgeier H., Gasparini F., Kuhn R., Hess S.D., Velicelebi G., and Johnson E.C. J. Pharmacol. Exp. Ther. 290 (1999) 170
9. Gasparini F., Lingenhohl K., Stoehr N., Flor P.J., Heinrich M., Vranesic I., Biollaz M., Allgeier H., Heckendorn R., Urwyler S., Varney M.A., Johnson E.C., Hess S.D., Rao S.P., Sacaan A.I., Santori E.M., Velicelebi G., and Kuhn R. Neuropharmacology 38 (1999) 1493
10. Gasparini F., Floersheim P., Flor P.J., Heinrich M., Inderbitzin W., Ott D., Pagano A., Stierlin C., Stoehr N., Vranesic I., and Kuhn R. Farmaco 56 (2001) 95
11. Mathiesen J.M., Svendsen N., Osborne H.B., Thomsen C., and Ramirez M.T. Br. J. Pharmacol. 138 (2003) 1026
12. Green M.D., Jiang X., and King C.D. Life Sci. 75 (2004) 947
13. Cosford N.D., Tehrani L., Roppe J., Schweiger E., Smith N.D., Anderson J., Bristow L., Brodkin J., Jiang X., McDonald I., Rao S., Washburn M., and Varney M.A. J. Med. Chem. 46 (2003) 204
14. Yang X., and Chen W. Xenobiotica 35 (2005) 797
15. Palczewski K., Kumasaka T., Hori T., Behnke C.A., Motoshima H., Fox B.A., Le Trong I., Teller D.C., Okada T., Stenkamp R.E., Yamamoto M., and Miyano M. Science 289 (2000) 739
16. A putative binding site is depicted in Figure 2, the details of the homology modeling will be published elsewhere.
17. Pagano A., Ruegg D., Litschig S., Stoehr N., Stierlin C., Heinrich M., Floersheim P., Prezeau L., Carroll F., Pin J.P., Cambria A., Vranesic I., Flor P.J., Gasparini F., and Kuhn R. J. Biol. Chem. 275 (2000) 33750
18. Malherbe P., Kratochwil N., Zenner M.T., Piussi J., Diener C., Kratzeisen C., Fischer C., and Porter R.H. Mol. Pharmacol. 64 (2003) 823
19. Roppe J., Smith N.D., Huang D., Tehrani L., Wang B., Anderson J., Brodkin J., Chung J., Jiang X., King C., Munoz B., Varney M.A., Prasit P., and Cosford N.D. J. Med. Chem. 47 (2004) 4645
20. 2O·HBr) C, H, N. The spectral and analytical data for all other compounds are reported in Supporting information.
21. 50 and slope factor (N) were obtained by using the program MLAB.
22. Shi Q., Savage J.E., Hufeisen S.J., Rauser L., Grajkowska E., Ernsberger P., Wroblewski J.T., Nadeau J.H., and Roth B.L. J. Pharmacol. Exp. Ther. 305 (2003) 131
23. Iso Y., Grajkowska E., Wroblewski J.T., Davis J., Goeders N.E., Johnson K.M., Sanker S., Roth B.L., Tueckmantel W., and Kozikowski A.P. J. Med. Chem. 49 (2006) 1080
24. Slassi A., Isaac M., Edwards L., Minidis A., Wensbo D., Mattsson J., Nilsson K., Raboisson P., McLeod D., Stormann T.M., Hammerland L.G., and Johnson E. Curr. Top. Med. Chem. 5 (2005) 897
25. Bonnefous C., Vernier J.M., Hutchinson J.H., Chung J., Reyes-Manalo G., and Kamenecka T. Bioorg. Med. Chem. Lett. 15 (2005) 1197