trans-2,3-dihydroxy-6a,7,8,12b-tetrahydro-6H-chromeno[3,4-c]isoquinoline: Synthesis, resolution, and preliminary pharmacological characterization of a new dopamine D1 receptor full agonist

Journal of Medicinal Chemistry

Volumn 49, Issue 23, 2006, Pages 6848-6857

  Cueva, Juan Pablo ^a   Giorgioni, Gianfabio ^a,b   Grubbs, Russell A ^a   Chemel, Benjamin R ^a   Watts, Val J ^a   Nichols, David E ^a  

^a PURDUE UNIVERSITY   (United States)

^b UNIVERSITY OF CAMERINO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 NITROCHROMENE; 2,3 DIHYDROXY 6A,7,8,12B TETRAHYDRO 6H CHROMENO[3,4 C]ISOQUINOLINE; 8 CHLORO 2,3,4,5 TETRAHYDRO 3 METHYL 5 PHENYL 1H 3 BENZAZEPIN 7 OL HYDROGEN MALEATE; ADROGOLIDE; BORONIC ACID DERIVATIVE; CHLORPROMAZINE; CHROMENE DERIVATIVE; CHROMENE TRIFLATE; DIHYDREXIDINE; DOPAMINE 1 RECEPTOR; DOPAMINE 1 RECEPTOR STIMULATING AGENT; DOXANTHRINE; ISOQUINOLINE DERIVATIVE; LEVODOPA; QUINPIROLE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; PHARMACOPHORE; SUZUKI REACTION;

ANIMALS; BENZOPYRANS; BINDING, COMPETITIVE; CELL LINE; CORPUS STRIATUM; CRYSTALLOGRAPHY, X-RAY; CYCLIC AMP; HUMANS; ISOQUINOLINES; MOLECULAR STRUCTURE; PHENANTHRIDINES; PSYCHOTROPIC DRUGS; RADIOLIGAND ASSAY; RATS; RECEPTORS, DOPAMINE D1; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; SWINE;

EID: 33751001333     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0604979     Document Type: Article

References (33)

1. Kebabian, J. W.; Tarazi, F. I.; Kula, N. S.; Baldessarini, R. J. Compounds selective for dopamine receptor subtypes. Drug Discovery Today 1997, 333-340.
2. Huang, X.; Lawler, C. P.; Lewis, M. M.; Nichols, D. E.; Mailman, R. B. D1 dopamine receptors. Int. Rev. Neurobiol. 2001, 48, 65-139.
3. Neve, K. A.; Seamans, J. K.; Trantham-Davidson, H. Dopamine receptor signaling. J. Recept. Signal Transduction Res. 2004, 24, 165-205.
4. Burns, R. S.; Chiueh, C. C.; Markey, S. P.; Ebert, M. H.; Jacobowitz, D. M.; Kopin, I. J. A primate model of parkinsonism: selective destruction of dopaminergic neurons in the pars compacta of the substantia nigra by N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine. Proc. Natl. Acad. Sci. U.S.A. 1983, 80, 4546-4550.
5. Jenner, P. The rationale for the use of dopamine agonists in Parkinson's disease. Neurology 1995, 45, S6-S12.
6. Sawaguchi, T.; Goldman-Rakic, P. S. D1 dopamine receptors in prefrontal cortex: involvement in working memory. Science 1991, 251, 947-950.
7. Huang, Y. Y.; Kandel, E. R. D1/D5 receptor agonists induce a protein synthesis-dependent late potentiation in the CA1 region of the hippocampus. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 2446-2450.
8. Goldman-Rakic, P. S.; Castner, S. A.; Svensson, T. H.; Siever, L. J.; Williams, G. V. Targeting the dopamine D(1) receptor in schizophrenia: insights for cognitive dysfunction. Psychopharmacology (Berlin) 2004.
9. Schultz, W. Getting formal with dopamine and reward. Neuron 2002, 36, 241-263.
10. Self, D. W.; Barnhart, W. J.; Lehman, D. A.; Nestler, E. J. Opposite modulation of cocaine-seeking behavior by D1- and D2-like dopamine receptor agonists. Science 1996, 271, 1586-1589.
11. Riggs, R. M.; McKenzie, A. T.; Byrn, S. R.; Nichols, D. E.; Foreman, M. M.; Truex, L. L. Effect of β-alkyl substitution on D-1 dopamine agonist activity: absolute configuration of β-methyldopamine. J. Med. Chem. 1987, 30, 1914-1918.
12. Brewster, W. K.; Nichols, D. E.; Riggs, R. M.; Mottola, D. M.; Lovenberg, T. W.; Lewis, M. H.; Mailman, R. B. trans-10,11-Dihydroxy-5,6,6a,7,8,12b- hexahydrobenzo[a]phenanthridine: a highly potent selective dopamine D1 full agonist. J. Med. Chem. 1990, 33, 1756-1764.
13. Taylor, J. R.; Lawrence, M. S.; Redmond, D. E., Jr.; Elsworth, J. D.; Roth, R. H.; Nichols, D. E.; Mailman, R. B. Dihydrexidine, a full dopamine D1 agonist, reduces MPTP-induced parkinsonism in monkeys. Eur. J. Pharmacol. 1991, 199, 389-391.
14. Rascol, O.; Blin, O.; Thalamas, C.; Descombes, S.; Soubrouillard, C.; Azulay, P.; Fabre, N.; Viallet, F.; Lafnitzegger, K.; Wright, S.; Carter, J. H.; Nutt, J. G. ABT-431, a D1 receptor agonist prodrug, has efficacy in Parkinson's disease. Ann. Neurol. 1999, 45, 736-741.
15. Ghosh, D.; Snyder, S. E.; Watts, V. J.; Mailman, R. B.; Nichols, D. E. 8,9-Dihydroxy-2,3,7,11b-tetrahydro-1H-naph[1,2,3-de]isoquinoline: a potent full dopamine D1 agonist containing a rigid β-phenyldopamine pharmacophore. J. Med. Chem. 1996, 39, 549-555.
16. Grubbs, R. A.; Lewis, M. M.; Owens-Vance, C.; Gay, E. A.; Jassen, A. K.; Mailman, R. B.; Nichols, D. E. 8,9-Dihydroxy-1,2,3,11b-tetrahydrochromeno[4,3,2, -de]isoquinoline (dinoxyline), a high affinity and potent agonist at all dopamine receptor isoforms. Bioorg. Med. Chem. 2004, 12, 1403-1412.
17. Sit, S. Y.; Xie, K.; Jacutin-Porte, S.; Boy, K. M.; Seanz, J.; Taber, M. T.; Gulwadi, A. G.; Korpinen, C. D.; Burris, K. D.; Molski, T. F.; Ryan, E.; Xu, C.; Verdoorn, T.; Johnson, G.; Nichols, D. E.; Mailman, R. B. Synthesis and SAR exploration of dinapsoline analogues. Bioorg. Med. Chem. 2004, 12, 715-734.
18. Horn, A. S.; Kaptein, B.; Mulder, T. B.; de Vries, J. B.; Wynberg, H. 6,7-Dihydroxy-3-chromanamine: synthesis and pharmacological activity of an oxygen isostere of the dopamine agonist 6,7-dihydroxy-2-aminotetralin. J. Med. Chem. 1984, 27, 1340-1343.
19. Hutchinson, A.; Williams, M.; de Jesus, R.; Stone, G. A.; Sylvester, L.; Clarke, F. H.; Sills, M. A. 2H-[1]Benzopyrano[3,4-e]pyridines: synthesis and activity at central monoamine receptors. J. Med. Chem. 1989, 32, 720-727.
20. Pal, K. An improved synthesis of 5-ethenyl-4a-methyl-2-oxo-2,3,4,4a,7,8- hexahydro-naphthalene and similar 1,3-dienes using palladium catalyzed cross coupling methodology. Synthesis 1995, 1485-1487.
21. Glennon, R. A.; Liebowitz, S. M. Serotonin receptor affinity of cathinone and related analogues. J. Med. Chem. 1982, 25, 393-397.
22. Murray, M.; Ryan, A. J.; Little, P. J. Inhibition of rat hepatic microsomal aminopyrine W-demethylase activity by benzimidazole derivatives. Quantitative structure-activity relationships. J. Med. Chem. 1982, 25, 887-892.
23. Qandil, A. M.; Lewis, M. M.; Jassen, A.; Leonard, S. K.; Mailman, R. B.; Nichols, D. E. Synthesis and pharmacological evaluation of substituted naphth[1,2,3-de]isoquinolines (dinapsoline analogues) as D(1) and D(2) dopamine receptor ligands. Bioorg. Med. Chem. 2003, 11, 1451-1464.
24. Shulgin, A. T. Convenient synthesis of myristicinaldehyde. Can. J. Chem. 1968, 46, 75-77.
25. Michaelides, M. R.; Hong, Y.; Didomenico, S.; Bayburt, E. K.; Asin, K. E.; Britton, D. R.; Lin, C. W.; Shiosaki, K. Substituted hexahydrobenzo[f] thieno[c]quinolines as dopamine D1-selective agonists: synthesis and biological evaluation in vitro and in vivo. J. Med. Chem. 1997, 40, 1585-1599.
26. Dauzonne, D.; Royer, D. A Convenient one-pot synthesis of 2-unsubstituted 3-nitro-2H-chromenes. Synthesis 1984, 348-349.
27. Neirabeyeh, M. A.; Raynaud, D.; Podona, T.; Ou, L.; Perdicakis, C.; Coudert, G.; Guillaumet, G.; Pichat, L.; Gharib, A.; Sarda, N. Methoxy and hydroxy derivatives of 3,4-dihydro-3-(di-n-propylamino)-2H-1-benzopyrans: new synthesis and dopaminergic activity. Eur. J. Med. Chem. 1991, 26, 497-504.
28. Ono, N. The Nitro Group in Organic Synthesis; Wiley-VCH: New York, 2001; pp 176-177.
29. Knoerzer, T. A.; Nichols, D. E.; Brewster, W. K.; Watts, V. J.; Mottola, D.; Mailman, R. B. Dopaminergic benzo[a]phenanthridines: resolution and pharmacological evaluation of the enantiomers of dihydrexidine, the full efficacy D1 dopamine receptor agonist. J. Med. Chem. 1994, 37, 2453-2460.
30. 4 dopamine receptors. Psychopharmacology (Berlin) 1999, 141, 83-92.
31. 2 dopamine receptors. Mol. Pharmacol. 1996, 50, 966-976.
32. Hulme, E. C. Receptor-Ligand Interactions: A Practical Approach; IRL Press at Oxford University Press: Oxford, U.K., 1992; pp 198-199.
33. Watts, V. J.; Lawler, C. P.; Gilmore, J. H.; Southerland, S. B.; Nichols, D. E.; Mailman, R. B. Dopamine D1 receptors: efficacy of full (dihydrexidine) vs. partial (SKF38393) agonists in primates vs. rodents. Eur. J. Pharmacol. 1993, 242, 165-172.