Synthesis of bivalent ligands of β-carboline-3-carboxylates via a palladium-catalyzed homocoupling process

Tetrahedron Letters

Volumn 46, Issue 37, 2005, Pages 6363-6368

  Yin, Wenyuan ^a   Sarma, P V V Srirama ^a   Ma, Jun ^a   Han, Dongmei ^a   Chen, Jessica L ^a   Cook, James M ^a  

^a UNIVERSITY OF WISCONSIN MILWAUKEE   (United States)

Author keywords

Carbolines; CCt; Bivalent ligands; Homocoupling

Indexed keywords

BETA CARBOLINE 3 CARBOXYLIC ACID TERT BUTYL ESTER; CARBOLINE DERIVATIVE; IODO BETA CARBOLINE 3 CARBOXYLATE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; DRUG STRUCTURE; DRUG SYNTHESIS; SONOGASHIRA REACTION;

EID: 23744439100     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.07.022     Document Type: Article

References (49)

1. I. Wickelgren Science 283 1999 14
2. W. Ogris, A. Poeltl, B. Hauer, M. Ernst, A. Oberto, P. Wulff, H. Hoger, W. Wisden, and W. Sieghart Biochem. Pharmacol. 68 2004 1621
3. U. Rudolph, F. Crestani, and H. Mohler Trends Pharmacol. Sci. 22 2001 188
4. E. Costa, J. Auta, D.R. Grayson, K. Matsumoto, G.D. Pappas, X. Zhang, and A. Guidotti Neuropharmacology 43 2002 925
5. J.F. Tallman, S.M. Paul, P. Skolnick, and D.W. Gallager Science 207 1980 274
6. M. Nielsen, O. Gredal, and C. Braestrup Life Sci. 25 1979 679
7. C. Braestrup, M. Nielsen, and C. Olsen Proc. Natl. Acad. Sci. U.S.A. 77 1980 2288
8. M. Cain, R.W. Weber, F. Guzman, J.M. Cook, S.A. Barker, K.C. Rice, J.N. Crawley, S.M. Paul, and P. Skolnick J. Med. Chem. 25 1982 1081
9. P.T. Ninan, T.M. Insel, R.M. Cohen, J.M. Cook, P. Skolnick, and S.M. Paul Science 218 1982 1332
10. E.D. Cox, T.J. Hagen, R.M. McKernan, and J.M. Cook Med. Chem. Res. 5 1995 710
11. K.L. Foster, P.F. McKay, R. Seyoum, D. Milbourne, W. Yin, P.V.V.S. Sarma, J.M. Cook, and H.L. June Neuropsychopharmacology 29 2004 269
12. R.M.M. de Almeida, J.K. Rowlett, J.M. Cook, W.Y. Yin, and K.A. Miczek Psychopharmacology (Berlin, Germany) 172 2004 255
13. S.L. Gourley, J.F. DeBold, W. Yin, J.M. Cook, and K.A. Miczek Psychopharmacology (Berlin, Germany) 178 2005 232
14. J.K. Rowlett, J.M. Cook, A.N. Duke, and D.M. Platt CNS Spectrums 10 2005 40
15. C. Parnois, E. Cox, J.M. Cook, and J. Bergman Psychopharmacology (Berlin, Germany) 156 2001 461
16. S. Lelas, J.K. Rowlett, R.D. Spealman, J.M. Cook, C. Ma, X. Li, and W. Yin Psychopharmacology (Berlin, Germany) 161 2002 180
17. D.M. Platt, J.K. Rowlett, R.D. Spealman, J.M. Cook, and C. Ma Psychopharmacology (Berlin, Germany) 164 2002 151
18. S.C. Harvey, K.L. Foster, P.F. McKay, M.R. Carroll, R. Seyoum, J.E. Woods II, C. Grey, C.M. Jones, S. McCane, R. Cummings, D. Mason, C. Ma, J.M. Cook, and H.L. June J. Neurosci. 22 2002 3765
19. H.L. June, K.L. Foster, P.F. McKay, R. Seyoum, J.E. Woods, S.C. Harvey, J.A. Eiler William, C. Grey, M.R. Carroll, S. McCane, C.M. Jones, W. Yin, D. Mason, R. Cummings, M. Garcia, C. Ma, P.V.V.S. Sarma, J.M. Cook, and P. Skolnick Neuropsychopharmacology 28 2003 2124
20. M.M. Savic, D.I. Obradovic, N.D. Ugresic, J.M. Cook, W. Yin, and D.R. Bokonjic Pharmacol. Biochem. Behav. 79 2004 279
21. P.S. Portoghese J. Med. Chem. 44 2001 2259
22. S. Halazy Expert Opinion Therapeutic Patents 9 1999 431
23. P.S. Portoghese, C. Lin, F. Farouz-Grant, and A.E. Takemori J. Med. Chem. 37 1994 1495
24. X. Li, H. Cao, C. Zhang, R. Furtmueller, K. Fuchs, S. Huck, W. Sieghart, J. Deschamps, and J.M. Cook J. Med. Chem. 46 2003 5567
25. Q. Huang, E.D. Cox, T. Gan, C. Ma, D.W. Bennett, R.M. McKernan, and J.M. Cook Drug. Des. Discov. 16 1999 55
26. Q. Huang, X. He, C. Ma, R. Liu, S. Yu, C.A. Dayer, G.R. Wenger, R. McKernan, and J.M. Cook J. Med. Chem. 43 2000 71
27. X. He, Q. Huang, C. Ma, S. Yu, R. McKernan, and J.M. Cook Drug Design Disc. 17 2000 131 171
28. E.D. Cox, and J.M. Cook Chem. Rev. 95 1995 1797
29. E. Cox, L. Hamaker, J. Li, P. Yu, K. Czerwinski, L. Deng, D.W. Bennett, and J.M. Cook J. Org. Chem. 62 1997 44
30. H.R. Snyder, H.G. Walker, and F.X. Werber J. Am. Chem. Soc. 71 1949 527
31. S. Agarwal, A. Saxena, and P. Jain Indian J. Chem. 19B 1980 45
32. S. Ohta, A. Shimabayashi, M. Aono, and M. Okamoto Synthesis 1982 833
33. Ma, C. Ph.D. thesis 2000, University of Wisconsin-Milwaukee, Milwaukee, WI.
34. June, H. L.; Cook, J. M.; Ma, C. 2003, U.S. Patent Appl. Publ., 2003, 60 pp. CODEN: USXXCO US 2003176456 A1 20030918 CAN 139:241570 An 2003:737374 CAPLUS.
35. D. Janssen, and C. Wilson Org. Synth. Coll. Vol. IV 1963 547
36. T.J. Hagen, F. Guzman, C. Schultz, J.M. Cook, P. Skolnick, and H.E. Shannon Heterocycles 24 1986 2845
37. K. Sonogashira J. Organometal. Chem. 653 2002 46
38. T. Fukuyama, M. Shinmen, S. Nishitani, M. Sato, and I. Ryu Org. Lett. 4 2002 1691
39. Y. Nishihara, K. Ikegashira, K. Hirabayashi, J.I. Ando, A. Mori, and T. Hiyama J. Org. Chem. 65 2000 1780
40. J.L. Sessler, and R. Wang J. Org. Chem. 63 1998 4079
41. D.L. Boger, W. Jiang, and J. Goldberg J. Org. Chem. 64 1999 7094
42. M.J. Mio, L.C. Kopel, J.B. Braun, T.L. Gadzikwa, K.L. Hull, R.G. Brisbois, C.J. Markworth, and P.A. Grieco Org. Lett. 4 2002 3199
43. D.H. Cho, J.H. Lee, and B.H. Kim J. Org. Chem. 64 1999 8048
44. A. Lei, M. Srivastava, and X. Zhang J. Org. Chem. 67 2002 1969
45. F. Jung, A. Burger, and J.F. Biellmann Org. Lett. 5 2003 383
46. A.S. Hay J. Org. Chem. 27 1962 3320
47. G. Eglinton, and W. McCrae Adv. Org. Chem. 4 1963 225
48. Zhang, C. C. Ph.D. thesis 2004. University of Wisconsin-Milwaukee, Milwaukee, WI.
49. ++1 100).