Structure-activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB 1 and CB 2 receptors: Steric and electronic effects of naphthoyl substituents. New highly selective CB 2 receptor agonists

Bioorganic and Medicinal Chemistry

Volumn 13, Issue 1, 2005, Pages 89-112

  Huffman, John W ^a   Zengin, Gulay ^a   Wu, Ming Jung ^a   Lu, Jianzhong ^a   Hynd, George ^a   Bushell, Kristen ^a   Thompson, Alicia L S ^a   Bushell, Simon ^a   Tartal, Cindy ^b   Hurst, Dow P ^b   Reggio, Patricia H ^b   Selley, Dana E ^c   Cassidy, Michael P ^c   Wiley, Jenny L ^c   Martin, Billy R ^c  

^a CLEMSON UNIVERSITY   (United States)

^b KENNESAW STATE UNIVERSITY   (United States)

^c UNIVERSITY OF RICHMOND   (United States)

Author keywords

Aminoalkylindole; Cannabinoid receptors; Cannabinoids; Structure activity relationships

Indexed keywords

1 PENTYL 3 (2 METHOXY 1 NAPHTHOYL)INDOLE; 1 PROPYL 2 (4 METHYL 1 NAPHTHOYL)INDOLE; 1 PROPYL 2 METHYL 3 (6 METHOXY 1 NAPHTHOYL)INDOLE; ALKYL GROUP; CANNABINOID 1 RECEPTOR; CANNABINOID 2 RECEPTOR; CANNABINOID CB2 RECEPTOR AGONIST; CANNABINOID RECEPTOR AGONIST; GUANOSINE TRIPHOSPHATE; INDOLE DERIVATIVE; JWH 120; JWH 151; JWH 267; METHYL GROUP; NAPHTHOL DERIVATIVE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; BINDING AFFINITY; DRUG EFFECT; DRUG SELECTIVITY; ELECTROCHEMISTRY; ENZYME ASSAY; MOLECULAR MODEL; RECEPTOR AFFINITY; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

ALKYLATION; ANIMALS; BINDING, COMPETITIVE; CHO CELLS; CRICETINAE; GUANOSINE 5'-O-(3-THIOTRIPHOSPHATE); INDOLES; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MODELS, MOLECULAR; RECEPTOR, CANNABINOID, CB1; RECEPTOR, CANNABINOID, CB2; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 9644281057     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2004.09.050     Document Type: Article

References (59)

1. Y. Gaoni, and R. Mechoulam J. Am. Chem. Soc. 86 1964 1648
2. R.K. Razdan Pharmacol. Rev. 38 1986 75
3. Rapaka, R. S.; Makriyannis, A. Structure-Activity Relationships of the Cannabinoids, NIDA Research Monograph 79; National Institute on Drug Abuse, Rockville, MD, 1987
4. R. Mechoulam, W.A. Devane, and R. Glaser L. Murphy A. Bartke Marijuana/Cannabinoids: Neurobiology and Neurophysiology 1992 CRC Boca Raton 1 33
5. J.W. Huffman, and J.A.H. Lainton Curr. Med. Chem. 3 1996 101
6. H.H. Seltzman Curr. Med. Chem. 6 1999 685
7. L.S. Melvin, M.R. Johnson, C.A. Herbert, G.M. Milne, and A.A. Weissman J. Med. Chem. 27 1984 67
8. M.R. Johnson, and L.S. Melvin R. Mechoulam Cannabinoids as Therapeutic Agents 1986 CRC Boca Raton, FL 121 145
9. L.A. Matsuda, S.J. Lolait, M.J. Brownstein, A.C. Young, and T.H. Bonner Nature 346 1990 561
10. M. Herkenham, A.B. Lynn, M.D. Little, M.R. Johnson, L.S. Melvin, D.R. De Costa, and K.C. Rice Proc. Natl. Acad. Sci. U.S.A. 87 1990 1932
11. R.G. Pertwee Curr. Med. Chem. 6 1999 635
12. S. Munro, K. Thomas, and M. Abu-Shar Nature (London) 365 1993 61
13. C.S. Breivogel, G. Griffin, V. Di Marzo, and B.R. Martin Mol. Pharmacol. 2001 155
14. M.R. Bell, T.E. D'Ambra, V. Kumar, M.A. Eissenstat, J.L. Herrmann, J.R. Wetzel, D. Rosi, R.E. Philion, S.J. Daum, D.J. Hlasta, R.K. Kullnig, J.H. Ackerman, D.R. Haubrich, D.A. Luttinger, E.R. Baizman, M.S. Miller, and S.J. Ward J. Med. Chem. 34 1991 1099
15. T.E. D'Ambra, K.G. Estep, M.R. Bell, M.A. Eissenstat, K.A. Josef, J. Ward, D.A. Haycock, E.R. Baizman, F.M. Casiano, N.C. Beglin, S.M. Chippari, J.D. Grego, R.K. Kullnig, and G.T. Daley J. Med. Chem. 35 1992 124
16. D.R. Compton, L.H. Gold, S.J. Ward, R.L. Balster, and B.R. Martin J. Pharmacol. Exp. Ther. 263 1992 1118
17. V.M. Showalter, D.R. Compton, B.R. Martin, and M.E. Abood J. Pharmacol. Exp. Ther. 278 1996 989
18. M.A. Eissenstat, M.R. Bell, T.E. D'Ambra, E.J. Alexander, S.J. Daum, J.H. Ackerman, M.D. Gruett, V. Kumar, K.G. Estep, E.M. Olefirowicz, J.R. Wetzel, M.D. Alexander, J.D. Weaver, D.A. Haycock, D.A. Luttinger, F.M. Casiano, S.M. Chippari, J.E. Kuster, J.I. Stevenson, and S.J. Ward J. Med. Chem. 1995 3094
19. J.W. Huffman, D. Dai, B.R. Martin, B.R. Martin, and D.R. Compton Bioorg. Med. Chem. Lett. 4 1994 563
20. J.L. Wiley, D.R. Compton, D. Dai, J.A.H. Lainton, M. Phillips, J.W. Huffman, and B.R. Martin J. Pharmacol. Exp. Ther. 285 1998 995
21. M.M. Aung, G. Griffin, J.W. Huffman, M.-J. Wu, C. Keel, B. Yang, V.M. Showalter, M.E. Abood, and B.R. Martin Drug Alcohol Depend. 60 2000 133
22. J.W. Huffman Curr. Med. Chem. 6 1999 705
23. J.W. Huffman Curr. Pharm. Des. 6 2000 1323
24. J.W. Huffman, R. Mabon, M.-J. Wu, J. Lu, R. Hart, D.P. Hurst, P.H. Reggio, J.L. Wiley, and B.R. Martin Bioorg. Med. Chem. 11 2003 539
25. T. Okauchi, M. Itonaga, T. Minami, T. Owa, K. Kitoh, and H. Yoshino Org. Lett. 2 2000 1485
26. S.T. Sergievskaya, and T.S. Safonova J. Gen. Chem. USSR Engl. Transl. 27 1957 1715
27. J.F.K. Wilshire Aust. J. Chem. 20 1967 575
28. J. Cason, and J.D. Wordie J. Org. Chem. 15 1950 617
29. The details of the synthesis of acids 13-15 are found in the dissertation of Gulay Zengin, Clemson University, May 2003
30. G. Snatzke, and K. Kunde Chem. Ber. 106 1973 1341
31. L.C. King J. Am. Chem. Soc. 66 1944 894
32. A. Ahmed, R.A. Bragg, J. Clayden, L.W. Lai, C. McCarthy, J.H. Pink, N. Westlund, and S.A. Yasin Tetrahedron 54 1998 13277
33. We thank Dr. C. W. Padgett for carrying out the X-ray determination. These data have been filed with the Cambridge Crystallographic Data Centre with deposition number CCDC 248000
34. Dai, D. Ph.D. dissertation, Clemson University, 1993
35. J.H. Nelson Nuclear Magnetic Resonance Spectroscopy 2003 Prentice Hall Upper Saddle River, NJ pp 254-276
36. C.C. Price, E.C. Chapin, A. Goldman, E. Krebs, and H.M. Shafer J. Am. Chem. Soc. 63 1941 1857
37. L.F. Fieser, and H.L. Holmes J. Am. Chem. Soc. 58 1936 2319
38. L. Gottlieb, D. Kellner, and H.J.E. Loewenthal Synth. Commun. 19 1989 2987
39. S. Cacchi, E. Morera, and G. Ortar Tetrahedron Lett. 26 1985 1109
40. A.J. Shand, and R.H. Thomson Tetrahedron 1963 1919
41. The details of the preparation of phenols 36 and 37 will be found in the dissertation of J. Lu, Clemson University, 2000
42. D.R. Compton, K.C. Rice, B.R. De Costa, R.K. Razdan, L.S. Melvin, M.R. Johnson, and B.R. Martin J. Pharmacol Exp. Ther. 265 1993 218
43. D.E. Selley, S. Stark, L.J. Sim, and S.R. Childers Life Sci. 59 1996 659
44. J.W. Huffman, J. Liddle, S. Yu, M.M. Aung, M.E. Abood, J.L. Wiley, and B.R. Martin Bioorg. Med. Chem. 7 1999 2905
45. J.W. Huffman, S.M. Bushell, J.R.A. Miller, J.L. Wiley, and B.R. Martin Bioorg. Med. Chem. 10 2002 4119
46. P.H. Reggio, S. Basu-Dutt, J. Barnett-Norris, M.T. Castro, D.P. Hurst, H.H. Seltzman, M.J. Roche, A.F. Gilliam, B.F. Thomas, L.A. Stevenson, R.G. Pertwee, and M.E. Abood J. Med. Chem. 41 1998 5177
47. S.D. McAllister, G. Rizvi, S. Anavi-Goffer, D.P. Hurst, J. Barnett-Norris, D.L. Lynch, P.H. Reggio, and M.E. Abood J. Med. Chem. 46 2003 5139
48. D. Shire, B. Calandra, M. Bouaboula, F. Barth, M. Rinaldi-Carmona, P. Casellas, and P. Ferrara Life Sci. 65 1999 627
49. D. Shire, B. Calandra, M. Delpech, X. Dumont, M. Kaghad, G. Le Fur, D. Caput, and P. Ferrara J. Biol. Chem. 271 1996 6941
50. F.G. Baddar, and F.L. Warren J. Chem. Soc. 1939 244
51. B.R. Martin, D.R. Compton, B.F. Thomas, W.R. Prescott, P.J. Little, R.K. Razdan, M.R. Johnson, L.S. Melvin, R. Mechoulam, and S.J. Ward Pharmacol. Biochem. Behav. 40 1991 471
52. Y.C. Cheng, and W.H. Prusoff Biochem. Pharmacol. 22 1973 3099
53. J.A. Ballesteros, and H. Weinstein P.M. Conn S.C. Sealfon Methods in Neuroscience Vol. 25 1995 Academic New York 366 428
54. P. Leff Trends Pharmacol. Sci. 16 1995 89
55. J. Barnett-Norris, D.P. Hurst, D.L. Lynch, F. Guarnieri, A. Makriyannis, and P.H. Reggio J. Med. Chem. 45 2002 3649
56. D.P. Hurst, D.L. Lynch, J. Barnett-Norris, S.M. Hyatt, H.H. Seltzman, M. Zhong, Z.H. Song, J. Nie, D. Lewis, and P.H. Reggio Mol. Pharmacol. 62 2002 1274
57. D. Shire, B. Calandra, M. Bouaboula, F. Barth, M. Rinaldi-Carmona, P. Casellas, and P. Ferrara Life Sci. 65 1999 627
58. S.K. Burley, and G.A. Petsko Science 229 1985 23
59. C.A. Hunter, J. Singh, and J.M. Thornton J. Mol. Biol. 218 1991 837