Novel 4-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)methylbenzofuran derivatives as selective α2C-adrenergic receptor antagonists

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 6, 2007, Pages 1616-1621

  Hagihara, Koji ^a   Kashima, Hajime ^a   Iida, Kyoichiro ^a   Enokizono, Junichi ^a   Uchida, Shin ichi ^a   Nonaka, Hiromi ^a   Kurokawa, Masako ^a   Shimada, Junichi ^a  

^a KYOWA HAKKO KOGYO CO LTD   (Japan)

Author keywords

2 Adrenergic receptor; Antagonist; Anti dyskinesia; Benzofuran

Indexed keywords

4 (6,7 DIMETHOXY 1,2,3,4 TETRAHYDROISOQUINOLIN 2 YL)METHYLBENZOFURAN 2 CARBOXAMIDE; ALPHA ADRENERGIC RECEPTOR STIMULATING AGENT; FIPAMEZOLE; IDAZOXAN; TETRAHYDROISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG; YOHIMBINE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BINDING AFFINITY; DRUG STRUCTURE; DRUG SYNTHESIS; DYSKINESIA; HUMAN; HUMAN CELL; MARMOSET; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ADRENERGIC ALPHA-2 RECEPTOR ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANIMALS; BENZOFURANS; CALLITHRIX; DOPAMINE AGENTS; DYSKINESIA, DRUG-INDUCED; HUMANS; INDICATORS AND REAGENTS; ISOQUINOLINES; LEVODOPA; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33847066997     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.12.094     Document Type: Article

References (35)

1. Hoffman B.B., and Lefkowitz R.J. Annu. Rev. Pharmarcol. Toxicol. 20 (1980) 581
2. Gerhardt M.A., and Neubig R.R. Mol. Pharmacol. 40 (1991) 707
3. Eason M.G., Kurose H., Holt B.D., Raymond J.R., and Liggett S.B. J. Biol. Chem. 267 (1992) 15795
4. Bylund D.B. FASEB J. 6 (1992) 832
5. Bylund D.B., Eikenberg D.C., Hieble J.P., Langer S.Z., Lefkowitz R.J., Minneman K.P., Molinoff P.B., Ruffolo Jr. R.R., and Trendelenburg U. Pharmacol. Rev. 46 (1994) 121
6. Hieble J.P., Bondinell W.E., and Ruffolo Jr. R.R. J. Med. Chem. 38 (1995) 3415
7. Hieble J.P., and Ruffolo Jr. R.R. Prog. Drug Res. 47 (1996) 81
8. Hieble J.P., Ruffolo Jr. R.R., Sulpizio A.C., Naselsky D.P., Conway T.M., Ellis C., Swift A.M., Ganguly S., and Bergsma D. J. Pharmacol. Commun. 6 (1995) 91
9. Nutt J.G. Neurology 40 (1990) 340
10. Stocchi F., Nordera G., and Marsden C.D. Clin. Neuropharmacol. 20 (1997) 95
11. Hurtig H.I. Exp. Neurol. 144 (1997) 10
12. Grondin R., Tahar A.H., Doan V.D., Ladure P., and Bedard P.J. Naunyn Schmiedeberg's Arch. Pharmacol. 361 (2000) 181
13. Brefel-Courbon C., Thalamas C., Peyro-Saint-Paul H., Senard J.-M., Montastruc J.-L., and Rascol O. CNS Drugs 10 (1998) 189
14. Henry B., Fox S.H., Peggs D., Crossman A.R., and Brotchie J.M. Mov. Dissord. 14 (1999) 744
15. Colpaert F.C. Neuropharmacology 26 (1987) 1431
16. Colpaert F.C., Degryse A.-D., and Craenendonck H.V. Brain Res. Bull. 26 (1991) 627
17. Bezard E., Brefel C., Tison F., Peyro-Saint-Paul H., Ladure P., Rascol O., and Gross C. Prog. Neuropsychopahrmacol. Biol. Psychiatry 23 (1999) 1237
18. Ghika J., Tennis M., Hoffman E., Schoenfeld D., and Growdon J. Neurology 41 (1991) 986
19. Savola J.-M., Hill M., Engstrom M., Merivuori H., Wurster S., McGuire S.G., Fox S.H., Crossman A.R., and Brotchie J.M. Mov. Dissord. 18 (2003) 872
20. MacDonald E., Kobilka B.K., and Scheinin M. Trends Pharmacol. Sci. 18 (1997) 211
21. Kashima, H.; Uesaka, N.; Suzuki, T.; Nonaka, H.; Enokizono, J.; Uchida, S.; Kanda, T.; Ushiki. J.; Shiozaki, S.; Shimada, J. Abstracts of Papers, The Japanese Pharmaceutical Society, 25th Medicinal Chemistry Symposium, November 29-December 1, 2006, Nagoya.
22. Hagihara, K.; Kashima, H.; Iida, K.; Otsubo, N.; Nonaka, H.; Enokizono, J.; Uchida, S.; Kurokawa, M.; Kanda, T.; Arai, H.; Shimada, J. Abstracts of Papers, The Japanese Pharmaceutical Society, 25th Medicinal Chemistry Symposium, November 29-December 1, 2006, Nagoya.
23. Corre M., and Hercouet A. Tetrahedron 37 (1981) 2855
24. Corre M., and Hercouet A. Tetrahedron 37 (1981) 2861
25. Corre M., and Hercouet A. Tetrahedron 37 (1981) 2866
26. Dalla V., and Cotelle P. Tetrahedron 55 (1999) 6923
27. Jones G., and Stanforth S.P. Organ. React. 49 (1997) 2
28. Smith R.A.J., and Manas A.R.B. Synthesis (1984) 166
29. Smith W.E. J. Org. Chem. 37 (1972) 3973
30. Cresp T.M., Sargent M.V., Elix J.A., and Murphy D.P. J. Chem. Soc. Perkin Trans. 1 (1973) 340
31. Dyke, H. J.; Lowe, C.; Montana, J. G.; Kendall, H. J.; Dabin, V. J. WO97/44337, 1997.
32. 2C adrenergic receptors.
33. Pearce R.K., Jackson M., Smith L., Jenner P., and Marsden C.D. Mov. Disord. 10 (1995) 731
34. Compounds 10e and 23d were simultaneously administered by po route to a marmoset at a dose of 2.5 mg/kg each. Blood samples were collected at appropriate time points and centrifuged to obtain plasma samples. Plasma concentrations of the both compounds were measured by LC/MS/MS. The area under plasma concentration time curve (AUC) was calculated by a trapezoidal method.
35. Schaak S., Cayla C., Blaise R., Quinchon F., and Paris H. J. Pharmacol. Exp. Ther. 281 (1997) 983