Further delineation of hydrophobic binding sites in dopamine D 2/D3 receptors for N-4 substituents on the piperazine ring of the hybrid template 5/7-{[2-(4-aryl-piperazin-1-yl)-ethyl]-propyl-amino}-5, 6,7,8-tetrahydro-naphthalen-2-ol

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 15, 2010, Pages 5661-5674

  Ghosh, Balaram ^a   Antonio, Tamara ^b   Gopishetty, Bhaskar ^a   Reith, Maarten ^b   Dutta, Aloke ^a  

^a WAYNE STATE UNIVERSITY   (United States)

^b NEW YORK UNIVERSITY   (United States)

Author keywords

D3 dopamine agonist; D3 receptor; Dopamine receptors; Parkinson's disease

Indexed keywords

1 (4 BIPHENYLYL)PIPERAZINE; 1 (PYRIDIN 3 YL)PIPERAZINE; 2 (4 (BIPHENYL 4 YL)PIPERAZIN 1 YL)ACETONITRILE; 2 (4 (BIPHENYL 4 YL)PIPERAZIN 1 YL)ETHANAMINE; 2 (4 (PYRIDIN 2 YL)PIPERAZIN 1 YL)ACETONITRILE; 2 (4 (PYRIDIN 2 YL)PIPERAZIN 1 YL)ETHANAMINE; 2 (4 (PYRIDIN 3 YL)PIPERAZIN 1 YL)ACETONITRILE; 2 (4 (PYRIDIN 3 YL)PIPERAZIN 1 YL)ETHANAMINE; 2 (4 (PYRIDIN 4 YL)PIPERAZIN 1 YL)ACETONITRILE; 2 (4 (PYRIDIN 4 YL)PIPERAZIN 1 YL)ETHANAMINE; 2 (4 (PYRIMIDIN 2 YL)PIPERAZIN 1 YL)ACETONITRILE; 2 (4 (PYRIMIDIN 2 YL)PIPERAZIN 1 YL)ETHANAMINE; 6 ((2 (4 (BIPHENYL 4 YL)PIPERAZIN 1 YL)ETHYL)(PROPYL)AMINO) 5,6,7,8 TETRAHYDRONAPHTHALEN 1 OL; 7 ((2 (4 (BIPHENYL 4 YL)PIPERAZIN 1 YL)ETHYL)(PROPYL)AMINO) 5,6,7,8 TETRAHYDRONAPHTHALEN 2 OL; 7 (PROPYL(2 (4 (PYRIDIN 2 YL)PIPERAZIN 1 YL)ETHYL)AMINO) 5,6,7,8 TETRAHYDRONAPHTHALEN 2 OL; 7 (PROPYL(2 (4 (PYRIDIN 3 YL)PIPERAZIN 1 YL)ETHYL)AMINO) 5,6,7,8 TETRAHYDRONAPHTHALEN 2 OL; 7 (PROPYL(2 (4 (PYRIDIN 4 YL)PIPERAZIN 1 YL)ETHYL)AMINO) 5,6,7,8 TETRAHYDRONAPHTHALEN 2 OL; 7 (PROPYL(2 (4 (PYRIMIDIN 2 YL)PIPERAZIN 1 YL)ETHYL)AMINO) 5,6,7,8 TETRAHYDRONAPHTHALEN 2 OL; 7 METHOXY N (2 (4 (PYRIDIN 3 YL)PIPERAZIN 1 YL)ETHYL) 1,2,3,4 TETRAHYDRONAPHTHALEN 2 AMINE; DOPAMINE 2 RECEPTOR; DOPAMINE 3 RECEPTOR; ISOQUINOLINE DERIVATIVE; LIGAND; N (2 (4 (BIPHENYL 4 YL)PIPERAZIN 1 YL)ETHYL) 7 METHOXY 1,2,3,4 TETRAHYDRONAPHTHALEN 2 AMINE; NAPHTHALENE DERIVATIVE; PALLADIUM; PIPERAZINE; PYRIDINE DERIVATIVE; ROPINIROLE; UNCLASSIFIED DRUG; UNINDEXED DRUG; 6-((2-(4-(BIPHENYL-4-YL)PIPERAZIN-1-YL)ETHYL)(PROPYL)AMINO)-5,6,7,8-TETRAHYDRONAPHTHALEN-1-OL; BIPHENYL DERIVATIVE; PIPERAZINE DERIVATIVE; TETRALIN DERIVATIVE;

AMINATION; ARTICLE; ATOM; BINDING AFFINITY; BINDING SITE; CATALYSIS; CELL STRAIN HEK293; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HYDROPHOBICITY; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; THIN LAYER CHROMATOGRAPHY; CELL LINE; CHEMICAL PHENOMENA; CHEMISTRY; METABOLISM; STEREOISOMERISM; SYNTHESIS;

BINDING SITES; BIPHENYL COMPOUNDS; CELL LINE; HUMANS; HYDROPHOBICITY; PIPERAZINES; RECEPTORS, DOPAMINE D2; RECEPTORS, DOPAMINE D3; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TETRAHYDRONAPHTHALENES; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS;

EID: 77955427417     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.06.025     Document Type: Article

References (22)

1. G. Emilien, J.-M. Maloteaux, M. Geurts, K. Hoogenberg, and S. Cragg Pharmacol. Ther. 84 1999 133
2. D. Vallone, R. Picetti, and E. Borrelli Neurosci. Biobehav. Rev. 24 2000 125
3. C. Missale, S.R. Nash, S.W. Robinson, M. Jaber, and M.G. Caron Physiol. Rev. 78 1998 189
4. A. Zhang, J.L. Neumeyer, and R.J. Baldessarini Chem. Rev. 107 2007 274
5. E.V. Kuzhikandathil, L. Westrich, S. Bakhos, and J. Pasuit Mol. Cell. Neurosci. 26 2004 144
6. S. Beom, D. Cheong, G. Torres, M.G. Caron, and K.M. Kim J. Biol. Chem. 279 2004 28304
7. P. Sokoloff, B. Giros, M.P. Martres, M. Andrieux, R. Besancon, C. Pilon, M.L. Bouthenet, E. Souil, and J.C. Schwartz Arzneimittelforschung 42 1992 224
8. J.N. Joyce, and M.J. Millan Curr. Opin. Pharmacol. 7 2007 100
9. J.M. Van Kampen, and C.B. Eckman J. Neurosci. 26 2006 7272
10. F. Boeckler, and P. Gmeiner Pharmacol. Ther. 112 2006 281
11. C.A. Heidbreder, and A.H. Newman Ann. N.Y. Acad. Sci. 1187 2010 4
12. F. Micheli, and C. Heidbreder Recent Pat. CNS Drug Disc. 1 2006 271
13. N. Sartania, and P.G. Strange J. Neurochem. 72 1999 2621
14. A.K. Dutta, S.K. Venkataraman, X.S. Fei, R. Kolhatkar, S. Zhang, and M.E. Reith Bioorg. Med. Chem. 12 2004 4361
15. S. Biswas, S. Hazeldine, B. Ghosh, I. Parrington, E. Kuzhikandathil, M.E. Reith, and A.K. Dutta J. Med. Chem. 51 2008 3005
16. S. Biswas, S. Zhang, F. Fernandez, B. Ghosh, J. Zhen, E. Kuzhikandathil, M.E. Reith, and A.K. Dutta J. Med. Chem. 51 2008 101
17. D.A. Brown, P.S. Kharkar, I. Parrington, M.E. Reith, and A.K. Dutta J. Med. Chem. 51 2008 7806
18. B. Ghosh, T. Antonio, J. Zhen, P. Kharkar, M.E. Reith, and A.K. Dutta J. Med. Chem. 53 2010 1023
19. J.P. Frederic Paul, and J.F. Hartwig J. Am. Chem. Soc. 116 1994 5969
20. W.W. Hoeve J. Org. Chem. 50 1985 4508
21. M.S. Jensen, R.S. Hoerrner, W. Li, D.P. Nelson, G.J. Javadi, P.G. Dormer, D. Cai, and R.D. Larsen J. Org. Chem. 70 2005 6034
22. T.T. Denton, X. Zhang, and J.R. Cashman J. Med. Chem. 48 2005 224