Synthesis and SAR exploration of dinapsoline analogues

Bioorganic and Medicinal Chemistry

Volumn 12, Issue 4, 2004, Pages 715-734

  Sit, Sing Yuen ^a   Xie, Kai ^a   Jacutin Porte, Swanee ^a   Boy, Kenneth M ^a   Seanz, James ^a   Taber, Matthew T ^a   Gulwadi, Amit G ^a   Korpinen, Carolyn D ^a   Burris, Kevin D ^a   Molski, Thaddeus F ^a   Ryan, Elaine ^a   Xu, Cen ^a   Verdoorn, Todd ^a   Johnson, Graham ^a   Nichols, David E ^b   Mailman, Richard B ^c  

^a BRISTOL MYERS SQUIBB   (United States)

^b PURDUE UNIVERSITY   (United States)

^c UNIVERSITY OF NORTH CAROLINA SCHOOL OF MEDICINE   (United States)

Author keywords

Dihydrexidine; Dinapsoline; Dopamine agonist; Dopamine D1 receptor; Parkinson's disease; SAR

Indexed keywords

ANTIPARKINSON AGENT; DINAPSOLINE; DOPAMINE 1 RECEPTOR STIMULATING AGENT; DOPAMINE 2 RECEPTOR; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; DRUG BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; RECEPTOR BINDING; STRUCTURE ACTIVITY RELATION;

EID: 0842265855     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2003.11.015     Document Type: Article

References (52)

1. Qandil A.M., Lewis M.M., Jassen A., Leonard S.K., Mailman R.B., Nichols D.E. Bioorg. Med. Chem. 11:2003;1451.
2. Sit S.Y., Xie K., Jacutin-Porte S., Taber M.T., Gulwadi A.G., Korpinen C.D., Burris K.D., Molski T.F., Ryan E., Xu C., Wong H., Zhu J., Krishnananthan S., Gao Q., Verdoorn T., Johnson G. J. Med. Chem. 45:2002;3660.
3. Ghosh D., Snyder S.E., Watts V.J., Mailman R.B., Nichols D.E. J. Med. Chem. 39:1996;549.
4. Siderowf A., Stern M. Ann. Intern. Med. 138:2003;651.
5. Neve K.A., Neve K.A. The Dopamine Receptors. 1997;Humana, Totowa, NJ.
6. Setler P.E., Sarau H.M., Zirkle C.L., Saunders H.L. Eur. J. Pharmacol. 50:1978;419.
7. Gilmore J.H., Watts V.J., Lawler C.P., Noll E.P., Nichols D.E., Mailman R.B. Neuropharmacology. 34:1995;481.
8. Watts V.J., Lawler C.P., Gonzales A.J., Zhou Q.Y., Civelli O., Nichols D.E., Mailman R.B. Synapse. 21:1995;177.
9. Watts V.J., Lawler C.P., Gilmore J.H., Southerland S.B., Nichols D.E., Mailman R.B. Eur. J. Pharmacol. 242:1993;165.
10. Taylor J.R., Lawrence M.S., Redmond D.E., Elsworth J.D., Roth R.H., Nichols D.E., Mailman R.B. Eur. J. Pharmacol. 199:1991;389.
11. Kebabian J.W., Britton D.R., DeNinno M.P., Perner R., Smith L., Jenner P., Schoenleber R., Williams M. Eur. J. Pharmacol. 229:1992;203.
12. Shiosaki K., Jenner P., Asin K.E., Britton D.R., Lin C.W., Michaelides M., Smith L., Bianchi B., Didomenico S., Hodges L., Hong Y., Mahan L., Mikusa J., Miller T., Nikkel A., Stashko M., Witte D., Williams M. J. Pharmacol. Exp. Ther. 276:1996;150.
13. 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. Ann. Neurol. 45:1999;736.
14. Mailman R.B., Huang X., Nichols D.E. Current Opinion in Investigational Drugs. 2(11):2001;1582.
15. Lewis M.M., Watts V.J., Lawler C.P., Nichols D.E., Mailman R.B. J. Pharmacol. Exp. Ther. 286:1998;345.
16. Asin K.E., Wirtshafter D. Eur. J. Pharmacol. 235:1993;167.
17. Gulwadi A.G., Korpinen C.D., Mailman R.B., Nichols D.E., Sit S.Y., Taber M.T. J. Pharmacol. Exp. Ther. 296:2001;338.
18. Brewster W.K., Nichols D.E., Riggs R.M., Mottola D.M., Lovenberg T.W., Lewis M.H., Mailman R.B. J. Med. Chem. 33:1990;1756.
19. Mailman, R. B.; Gay, E. A. Med. Chem. Res. In press.
20. Kilts J.D., Connery H.S., Arrington E.G., Lewis M.M., Lawler C.P., Oxford G.S., O'Malley K.L., Todd R.D., Blake B.L., Nichols D.E., Mailman R.B. J. Pharmacol. Exp. Ther. 301:2002;1179.
21. Knoerzer T.A., Watts V.J., Nichols D.E., Mailman R.B. J. Med. Chem. 38:1995;3062.
22. Gronowitz S., Hoernfeldt A.-B., Temciuc M. Synthesis. 5:1993;483.
23. Mathison I.W., Morgant P.H. J. Org. Chem. 39:2003;3211.
24. Clark J.H., Wails D., Jones C.W., Smith H., Boechat N., Mayer L.U., Mendonca J.S. J. Chem. Res. 1994;478. Synop. 1994.
25. Majetich G., Hicks R., Reister S. J. Org. Chem. 62:1997;4321.
26. White J.D., Hrnciar P., Stappenbeck F. J. Org. Chem. 62:1997;5250.
27. Takakis I., Hadjimihalakis P.M., Tsantali G.G., Pilini H. J. Heterocycl. Chem. 29:1992;123.
28. Iqbal N., Wei Z.-Y., Baker G.B., Knaus E.E. Canadian J. Chem. 75:1997;601.
29. Bellas S. J. Chem. Soc. 1964;4561.
30. Schlosser M., Simig G., Geneste H. Tetrahedron. 54:1998;9023.
31. Kucznierz R., Dickhaut J., Leinert H., Von Der Saal W. Synth. Commun. 29:1999;1617.
32. Pomerantz C. Monatsh. Chem. 14:1893;116.
33. Cram D.J., Brown S.B., Taguchi T., Feigel M., Maverick E., Trueblood K.N. J. Am. Chem. Soc. 106:1984;695.
34. Nichols D.E. The Development of Novel Dopamine Agonists. Kaiser C., Kebabian J.W. Dopamine Receptors. 1983;201-218 American Chemical Society, Washington, DC.
35. Mailman R.B., Nichols D.E., Tropsha A. Molecular Drug Design and Dopamine Receptors. Neve K.A., Neve R.L. The Dopamine Receptors. 1997;105-133 Humana Press, Totowa, NJ.
36. Mottola D.M., Laiter S., Watts V.J., Tropsha A., Wyrick S.D., Nichols D.E., Mailman R.B. J. Med. Chem. 39:1996;285.
37. Seiler M.P., Markstein R. Mol. Pharmacol. 26:1984;452.
38. Holden, K. G., Alkylthio-7,8-dihdroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3- benzazepines having dopaminergic activity. Patent US 4206210, 1980.
39. Wei C.-C., Teitel S. Heterocycles. 8:1977;97.
40. Hansch C., Hoekman D., Leo A., Zhang L., Li P. Toxicol. Lett. 79:1995;45.
41. Kim K.H. J. Pharm. Sci. 80:1991;966.
42. Holmes E., Sweatman B.C., Bollard M.E., Blackledge C.A., Beddell C.R., Wilson I.D., Lindon J.C., Nicholson J.K. Xenobiotica. 25:1995;1269.
43. Schaefer M., Okulicz-Kozaryn I., Batt A.M., Siest G., Loppinet V. J. Med. Chem. Chim. Ther. 16:1981;461.
44. Campbell N.R., Van Loon J.A., Sundaram R.S., Ames M.M., Hansch C., Weinshilboum R. Mol. Pharmacol. 32:1987;813.
45. Gnanalingham K.K., Erol D.D., Hunter A.J., Smith L.A., Jenner P., Marsden C.D. Psychopharmacology (Berl.). 117:1995;275.
46. DeNinno M.P., Schoenleber R., Perner R.J., Lijewski L., Asin K.E., Britton D.R., MacKenzie R., Kebabian J.W. J. Med. Chem. 34:1991;2561.
47. Noerzer T.A., Nichols D.E., Brewster W.K., Watts V.J., Mottola D., Mailman R.B. J. Med. Chem. 37:1994;2453.
48. Brewster W.K., Nichols D.E., Watts V.J., Riggs R.M., Mottola D., Mailman R.B. J. Med. Chem. 38:1995;318.
49. Mailman, R. B.; Gay, E. A. Med. Chem. Res. In press.
50. Asano Y., Yamashita M., Nagai K., Kuriyama M., Yamada K., Tomioka K. Tetrahedron Lett. 42:2001;8493.
51. Michaelides M.R., Hong Y., Didomenico S., Bayburt E.K., Asin K.E., Britton D.R., Lin C.W., Shiosaki K. J. Med. Chem. 40:1997;1585.
52. Burris K.D., Pacheco M.A., Filtz T.M., Kung M-P., Kung H.F., Molinoff P.B. Neuropsychopharmacology. 12:1995;335.