Synthesis and structure-activity relationships of a series of pyrrole cannabinoid receptor agonists

Bioorganic and Medicinal Chemistry

Volumn 11, Issue 18, 2003, Pages 3965-3973

  Tarzia, Giorgio ^a   Duranti, Andrea ^a   Tontini, Andrea ^a   Spadoni, Gilberto ^a   Mor, Marco ^b   Rivara, Silvia ^b   Plazzi, Pier Vincenzo ^b   Kathuria, Satish ^c   Piomelli, Daniele ^c  

^a UNIVERSITY OF URBINO   (Italy)

^b UNIVERSITY OF PARMA   (Italy)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

(2,5 DIMETHYL 1 PENTYL 1H PYRROL 3 YL)(NAPHTHALEN 1 YL)METHANONE; (2,5 DIMETHYL 1 PENTYL 1H PYRROL 3 YL)(PHENYL)METHANONE; (2,5 DIMETHYL 1 PROPYL 1H PYRROL 3 YL)(NAPHTHALEN 1 YL)METHANONE; (4 BROMO 2,5 DIMETHYL 1 PENTYL 1H PYRROL 3 YL)(NAPHTHALEN 1 YL)METHANONE; (4 BROMO 2,5 DIMETHYL 1 PENTYL 1H PYRROL 3 YL)(PHENYL)METHANONE; (4 BROMO 2,5 DIMETHYL 1 PROPYL 1H PYRROL 3 YL)(NAPHTHALEN 1 YL)METHANONE; 1 (2,5 DIMETHYL 1 PENTYL 1H PYRROL 3 YL) 4 HYDROXYBUTAN 1 ONE; 1 (4 CHLOROBENZYL) 2,5 DIMETHYL 1H PYRROL 3 YLNAPHTHALEN 1 YLMETHANONE; 2,3 DIHYDRO 5 METHYL 3 (MORPHOLINOMETHYL) 6 (1 NAPHTHOYL)PYRROLO[1,2,3 DE][1,4]BENZOXAZINE; 2,5 DIMETHYL 1 PENTYL 1H PYRROLE 3 CARBOXYLIC ACID CYCLOHEXYLAMIDE; CANNABINOID 1 RECEPTOR; CANNABINOID 2 RECEPTOR; CANNABINOID RECEPTOR AGONIST; JWH 007; JWH 161; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG; [1 (4 CHLOROBENZYL) 2,5 DIMETHYL 1H PYRROL 3 YL](PHENYL)METHANONE; [4 BROMO 1 (4 CHLOROBENZYL) 2,5 DIMETHYL 1H PYRROL 3 YL](NAPHTHALEN 1 YL)METHANONE;

AGONIST; ARTICLE; DRUG BINDING; DRUG DESIGN; DRUG SYNTHESIS; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

EID: 0042090319     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(03)00413-9     Document Type: Article

References (51)

1. Gaoni Y., Mechoulam R. J. Am. Chem. Soc. 86:1964;1646.
2. (a) Devane W.A., Dysarz F.A. III, Johnson M.R., Melvin L.S., Howlett A.C. Mol. Pharmacol. 34:1988;605
3. (b) Matsuda L.A., Lolait S.J., Brownstein M.J., Young A.C., Bonner T.I. Nature (London). 346:1990;561
4. (c) Gérard C.M., Mollereau C., Vassart G., Parmentier M. Biochem. J. 279:1991;129.
5. (a) Munro S., Thomas K.L., Abu-Shaar M. Nature (London). 365:1993;61
6. (b) Shire D., Calandra B., Rinaldi-Carmona M., Oustric D., Pessègue B., Bonnin-Cabanne O., Le Fur G., Caput D., Ferrara P. Biochim. Biophys. Acta. 1307:1996;132.
7. For a review see: Matsuda L.A. Crit. Rev. Neurobiol. 11:1997;143.
8. (a) Devane W.A., Hanus L., Breuer A., Pertwee R.G., Stevenson L.A., Griffin G., Gibson D., Mandelbaum A., Etinger A., Mechoulam R. Science. 258:1992;1946
9. (b) Mechoulam R., Ben-Shabat S., Hanus L., Ligumsky M., Kaminski N.E., Schatz A.R., Gopher A., Almog S., Martin B.R., Compton D.R., Pertwee R.G., Griffin G., Bayewitch M., Barg J., Vogel Z. Biochem. Pharmacol. 50:1995;83
10. (c) Sugiura T., Kondo S., Sukagawa A., Nakane S., Shinoda A., Itoh K., Yamashita A., Waku K. Biochem. Biophys. Res. Commun. 215:1995;89
11. (d) Hanus L., Abu-Lafi S., Fride E., Breuer A., Vogel Z., Shalev D.E., Kustanovich I., Mechoulam R. Proc. Natl. Acad. Sci. U.S.A. 98:2001;3662.
12. For a review, see: Pertwee R.G., Ross R.A. Prostaglandins Leucot. Essent. Fatty Acids. 66:2002;101.
13. (a) Williamson E.M., Evans F.J. Drugs. 60:2000;1303
14. (b) Pertwee R.G. Exp. Opin. Invest. Drugs. 9:2000;1553
15. (c) Piomelli D., Giuffrida A., Calignano A., Rodríguez de Fonseca F. Trends Pharmacol. Sci. 21:2000;218.
16. (a) Palmer S.L., Thakur G.A., Makriyannis A. Chem. Phys. Lipids. 121:2002;3
17. (b) Huffman J.W. Curr. Med. Chem. 6:1999;705
18. (c) Barth F., Rinaldi-Carmona M. Curr. Med. Chem. 6:1999;745
19. (d) Palmer S.L., Khanolkar A.D., Makriyannis A. Curr. Pharm. Des. 6:2000;1381.
20. Mechoulam R., Lander N., Breuer A., Zahalka J. Tetrahedron: Asymmetry. 1:1990;315.
21. Johnson, M. R. In Cannabinoids as Therapeutic Agents; Mechoulam, R., Ed. ; CRC: Boca Raton, FL, 1990; p 121.
22. D'Ambra T.E., Estep K.G., Bell M.R., Eissenstat M.A., Josef K.A., Ward S.J., Haycock D.A., Baizman E.R., Casiano F.M., Beglin N.C., Chippari S.M., Grego J.D., Kullnig R.K., Daley G.T. J. Med. Chem. 35:1992;124.
23. Huffman J.W., Dai D., Martin B.R., Compton D.R. Bioorg. Med. Chem. Lett. 4:1994;563.
24. Lainton J.A.H., Huffman J.W., Martin B.R., Compton D.R. Tetrahedron Lett. 36:1995;1401.
25. Huffman J.W., Lu J., Dai D., Kitaygorodskiy A., Wiley J.L., Martin B.R. Bioorg. Med. Chem. 8:2000;439.
26. Song Z.-H., Bonner T.I. Mol. Pharmacol. 49:1996;891.
27. Tao Q., McAllister S.D., Andreassi J., Nowell K.W., Cabral G.A., Hurst D.P., Bachtel K., Ekman M.C., Reggio P.H., Abood M.E. Mol. Pharmacol. 55:1999;605.
28. Song Z.H., Slowey C.A., Hurst D.P., Reggio P.H. Mol. Pharmacol. 56:1999;834.
29. (a) McAllister S.D., Tao Q., Barnett-Norris J., Buehner K., Hurst D.P., Guarnieri F., Reggio P.H., Nowell Harmon K.W., Cabral G.A., Abood M.E. Biochem. Pharmacol. 63:2002;2121
30. (b) Huffman J.W., Mabon R., Wu M.-J., Lu J., Hart R., Hurst D.P., Reggio P.H., Wiley J.L., Martin B.R. Bioorg. Med. Chem. 11:2003;539.
31. 3 solution, in the 298-328 K temperature range) is typical of a very strong intramolecular hydrogen bond: (a) Urry, D. W.; Ohnishi, T. In Peptides, Polypeptides and Proteins; Blout, E. R., Bovey, F. A., Goodman, M. and Lotan, N., Eds.; Wiley-Interscience: New York, 1974; p 230. (b) Urry D.W., Long M.M. CRC Crit. Rev. Biochem. 4:1976;1 (c) Gellman S.H., Dado G.P., Liang G.-B., Adams B.R. J. Am. Chem. Soc. 113:1991;1164.
32. 3 solution, in the 298-328 K temperature range) is typical of a very strong intramolecular hydrogen bond: (a) Urry, D. W.; Ohnishi, T. In Peptides, Polypeptides and Proteins; Blout, E. R., Bovey, F. A., Goodman, M. and Lotan, N., Eds.; Wiley-Interscience: New York, 1974; p 230. (b) Urry D.W., Long M.M. CRC Crit. Rev. Biochem. 4:1976;1 (c) Gellman S.H., Dado G.P., Liang G.-B., Adams B.R. J. Am. Chem. Soc. 113:1991;1164.
33. 3 solution, in the 298-328 K temperature range) is typical of a very strong intramolecular hydrogen bond: (a) Urry, D. W.; Ohnishi, T. In Peptides, Polypeptides and Proteins; Blout, E. R., Bovey, F. A., Goodman, M. and Lotan, N., Eds.; Wiley-Interscience: New York, 1974; p 230. (b) Urry D.W., Long M.M. CRC Crit. Rev. Biochem. 4:1976;1 (c) Gellman S.H., Dado G.P., Liang G.-B., Adams B.R. J. Am. Chem. Soc. 113:1991;1164.
34. Wiley J.L., Compton D.R., Dai D., Lainton J.A.H., Phillips M., Huffman J.W., Martin B.R. J. Pharmacol. Exp. Ther. 285:1998;995.
35. Aung M.M., Griffin G., Huffman J.W., Wu M.-J., Keel C., Yang B., Showalter V.M., Abood M.E., Martin B.R. Drug Alcohol Depend. 60:2000;133.
36. Showalter V.M., Compton D.R., Martin B.R., Abood M.E. J. Pharmacol. Exp. Ther. 278:1996;989.
37. Beddoes R.L., Dalton L., Joule J.A., Mills O.S., Street J.D., Watt C.I.F. J. Chem. Soc., Perkin Trans. 2. 1986;787.
38. Anderson H.J., Loader C.E., Xu R.X., Le N., Gogan N.J., McDonald R., Edwards L.G. Can. J. Chem. 63:1985;896. and references therein.
39. Karrer P., Smirnoff A.P. Helv. Chim. Acta. 5:1922;835.
40. Moussavi Z., Bonte J.P., Lesieur D., Leinot M., Lamar J.C., Tisne-Versailles J. Farmaco. 44:1989;77.
41. Knorr L. Chem. Ber. 18:1885;1558.
42. Aoyagi Y., Mizusaki T., Ohta A. Tetrahedron Lett. 37:1996;9203.
43. +), 94 (100).
44. Eissenstat M.A., Bell M.R., D'Ambra T.E., Alexander E.J., Daum S.J., Ackerman J.H., Gruett M.D., Kumar V., Estep K.G., Olefirowicz E.M., Wetzel J.R., Alexander M.D., Weaver J.D. III, Haycock D.A., Luttinger D.A., Casiano F.M., Chippari S.M., Kuster J.E., Stevenson J.I., Ward S.J. J. Med. Chem. 38:1995;3094.
45. Huffman J.W. Curr. Pharm. Des. 6:2000;1323.
46. 50 of 95.5±13.5.
47. Sybyl v. 6.7; Tripos Inc.: 1699 South Hanley Rd., St. Louis, MO, 63144, USA.
48. Clark M., Cramer R.D. III, van Opdenbosch N. J. Comput. Chem. 10:1989;982.
49. Powell M.J.D. Math. Progr. 12:1977;241.
50. Pindur U., Flo C. J. Heterocyclic Chem. 26:1989;1563.
51. Endo Laboratories. GB Patent 1161638, 1969; Chem. Abstr. 1970, 72, 3361.