Synthesis and binding studies of 2-O- and 11-O-substituted N-alkylnoraporphines

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 14, 2008, Pages 3971-3973

  Si, Yu Gui ^a   Gardner, Matthew P ^a   Tarazi, Frank I ^a   Baldessarini, Ross J ^a   Neumeyer, John L ^a  

^a MCLEAN HOSPITAL   (United States)

Author keywords

Aporphines; Binding affinities; Dopamine D1; Dopamine D2

Indexed keywords

2 (2 HYDROXYETHOXY) 11 HYDROXY N PROPYLNORAPORPHINE; ALKYL GROUP; APORPHINE DERIVATIVE; DOPAMINE 1 RECEPTOR; DOPAMINE 2 RECEPTOR; SEROTONIN 1A RECEPTOR;

ANIMAL TISSUE; ARTICLE; BRAIN TISSUE; DOPAMINERGIC SYSTEM; DRUG BINDING SITE; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG SYNTHESIS; FOREBRAIN; HYDROGEN BOND; LIPOPHILICITY; NONHUMAN; RAT; RECEPTOR AFFINITY; STEREOSPECIFICITY; STRUCTURE ACTIVITY RELATION;

ANIMALS; APORPHINES; CHEMISTRY, PHARMACEUTICAL; DRUG DESIGN; KINETICS; MODELS, CHEMICAL; PROSENCEPHALON; PROTEIN BINDING; RATS; RECEPTOR, SEROTONIN, 5-HT1A; RECEPTORS, DOPAMINE D1; RECEPTORS, DOPAMINE D2;

RATTUS;

EID: 47149085234     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.06.016     Document Type: Article

References (17)

1. Neumeyer J.L., Baldessarini R.J., and Booth R.G. In: Abraham D.J. (Ed). Burger's Medicinal Chemistry and Drug Discovery. Sixth ed. Vol. 6 (2003), John Wiley & Sons, New York 711 (Chapter 12)
2. Hsieh G.C., Hollingsworth P.R., Martino B., Chang R., Terranova M.A., O'Neill A.B., Lynch J.J., Moreland R.B., Donnelly-Roberts D.L., Kolasa T., Mikusa J.P., McVey J.M., Marsh K.C., Sullivan J.P., and Brioni J.D. J. Pharmacol. Exp. Ther. 308 (2004) 330
3. Subramony J.A. Mol. Pharm. 3 (2006) 380
4. Zhang A., Zhang Y., Branfman A.R., Baldessarini R.J., and Neumeyer J.L. J. Med. Chem. 50 (2007) 171
5. Gao Y., Zong R., Campbell A., Kula N.S., Baldessarini R.J., and Neumeyer J.L. J. Med. Chem. 31 (1988) 1392
6. Csutoras C., Zhang A., Zhang K., Kula N.S., Baldessarini R.J., and Neumeyer J.L. Bioorg. Med. Chem. 12 (2004) 3553
7. Søndergaard K., Kristensen J.L., Palner M., Gillings N., Knudsen G.M., Roth B.L., and Begtrup M. Org. Biomol. Chem. 3 (2005) 4077
8. Sipos A., Kiss B., Schmidt E., Greiner I., and Berényi S. Bioorg. Med. Chem. 16 (2008) 3773
9. Sipos A., Csutorás C., Berényi S., Uustare A., and Rinken A. Bioorg. Med. Chem. 16 (2008) 4563
10. Tóth M., Berényi S., Csutorás C., Kula N.S., Zhang K., Baldessarini R.J., and Neumeyer J.L. Bioorg. Med. Chem. 14 (2006) 1918
11. Ramsby S., Neumeyer J.L., Grigoriadis D., and Seeman P. J. Med. Chem. 32 (1989) 1198
12. Neumeyer J.L., Gao Y., Kula N.S., and Baldessarini R.J. J. Med. Chem. 33 (1990) 3122
13. Søndergaard K., Kristensen J.L., Gillings N., and Begtrup M. Eur. J. Org. Chem. (2005) 4428
14. Zhang A., Csutoras C., Zong R., and Neumeyer J.L. Org. Lett. 7 (2005) 3239
15. Si Y.-G., Gardner M.P., Tarazi F.I., Baldessarini R.J., and Neumeyer J.L. J. Med. Chem. 51 (2008) 983
16. Coop A., Lewis J.W., and Rice K.C. J. Org. Chem. 61 (1996) 6774
17. 2O: C, 62.26; H, 7.15; N, 3.46. Found: C, 62.26; H, 6.76; N, 3.48.