Design and synthesis of novel heterobiaryl amides as metabotropic glutamate receptor subtype 5 antagonists

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 7, 2007, Pages 2074-2079

  Kulkarni, Santosh S ^a   Newman, Amy Hauck ^a  

^a NATIONAL INSTITUTE ON DRUG ABUSE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 METHYL 6 (PHENYLETHYNYL)PYRIDINE; 3 [(2 METHYL 4 THIAZOLYL)ETHYNYL]PYRIDINE; 4 (3,5 DIFLUOROPHENYL) N (6 METHYLPYRIDIN 1 YL)PICOLINAMIDE; AROMATIC AMIDE; BROMOPICOLINAMIDE; CHLOROPICOLINAMIDE; METABOTROPIC RECEPTOR 5; METABOTROPIC RECEPTOR ANTAGONIST; PALLADIUM; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CATALYSIS; CHO CELL; CONTROLLED STUDY; CROSS COUPLING REACTION; DRUG ACTIVITY; DRUG DESIGN; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; FEMALE; IC 50; IN VITRO STUDY; NONHUMAN; STRUCTURE ACTIVITY RELATION;

AMIDES; ANIMALS; BINDING SITES; CHEMISTRY, PHARMACEUTICAL; CHO CELLS; CRICETINAE; CRICETULUS; DRUG DESIGN; MICE; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR CONFORMATION; RECEPTORS, METABOTROPIC GLUTAMATE; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTANCE-RELATED DISORDERS;

EID: 33947166901     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.12.083     Document Type: Article

References (30)

1. Conn P.J., and Pin J.P. Annu. Rev. Pharmacol. Toxicol. 37 (1997) 205
2. Gasparini F., Kuhn R., and Pin J.P. Curr. Opin. Pharmacol. 2 (2002) 43
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. Brodkin J., Busse C., Sukoff S.J., and Varney M.A. Pharmacol. Biochem. Behav. 23 (2002) 207
5. Tatarczynska E., Klodzinska A., Chojnacka-Wojcik E., Palucha A., Gasparini F., Kuhn R., and Pilc A. Br. J. Pharmacol. 132 (2001) 1423
6. Dolan S., Kelly J.G., Monteiro A.M., and Nolan A.M. Pain 106 (2003) 501
7. Yan Q.J., Rammal M., Tranfaglia M., and Bauchwitz R.P. Neuropharmacology 49 (2005) 1053
8. Li X., Need A.B., Baez M., and Witkin J.M. J. Pharmacol. Exp. Ther. 319 (2006) 254
9. Bear M.F. Genes Brain Behav. 4 (2005) 393
10. Popik P., and Wrobel M. Neuropharmacology 43 (2002) 1210
11. Paterson N.E., Semenova S., Gasparini F., and Markou A. Psychopharmacology (Berl.) 167 (2003) 257
12. Backstrom P., Bachteler D., Koch S., Hyytia P., and Spanagel R. Neuropsychopharmacology 29 (2004) 921
13. 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
14. 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
15. 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
16. Kulkarni S.S., Nightingale B., Dersch C.M., Rothman R.B., and Newman A.H. Bioorg. Med. Chem. Lett. 16 (2006) 3371
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. Malharbe P., Kratochwil N., Muhlemann A., Zenner M.T., Fischer C., Stahl M., Gerber P.R., Jaeschke G., and Porter R.H.P. J. Neurochem. 98 (2006) 601
20. 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
21. 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
22. 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
23. Bonnefous C., Vernier J.M., Hutchinson J.H., Chung J., Reyes-Manalo G., and Kamenecka T. Bioorg. Med. Chem. Lett. 15 (2005) 1197
24. Barder T.E., Walker S.D., Martinelli J.R., and Buchawald S.L. J. Am. Chem. Soc. 127 (2005) 4685
25. Wolfe J.P., Singer R.A., Yang B.H., and Buchwald S.L. J. Am. Chem. Soc. 121 (1999) 9550
26. Ishiyama T., Murata M., and Miyaura N. J. Org. Chem. 60 (1995) 7508
27. 2O) C, H, N. The experimental and spectral data for all other compounds are reported in the Supplementary information.
28. 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
29. Rodriguez A.L., Nong Y., Sekaran N.K., Alagille D., Tamagnan G.D., and Conn P.J. Mol. Pharmacol. 68 (2005) 1793
30. Paulis T.D., Hemstapat K., Chen Y., Zhang Y., Saleh S., Alagille D., Baldwin R.M., Tamagnan G.D., and Conn P.J. J. Med. Chem. 49 (2006) 3332