Chiral aryloxyalkylamines: Selective 5-HT1B/1D activation and analgesic activity

ChemMedChem

Volumn 5, Issue 5, 2010, Pages 696-704

  Carocci, Alessia ^a   Lentini, Giovanni ^a   Catalano, Alessia ^a   Cavalluzzi, Maria Maddalena ^a   Bruno, Claudio ^a   Muraglia, Marilena ^a   Colabufo, Nicola Antonio ^a   Galeotti, Nicoletta ^b   Corbo, Filomena ^a   Matucci, Rosanna ^b   Ghelardini, Carla ^b   Franchini, Carlo ^a  

^a UNIVERSITY OF BARI   (Italy)

^b UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Analgesia; Chirality; Receptors; Serotonin; Triptans

Indexed keywords

1 (2,3 DICHLOROPHENOXY) N METHYLPROPAN 2 AMINE HYDROCHLORIDE; 2 (2,3 DICHLOROPHENOXY) N METHYLETHANAMINE; 2 (2,3 DICHLOROPHENOXY) N METHYLPROPAN 1 AMINE; 2 (2,3 DICHLOROPHENOXY) N METHYLPROPAN 1 AMINE HYDROCHLORIDE; 2 [(1 NAPHTHYLOXY)METHYL]PYRROLIDINE; 2 [(1 NAPHTHYLOXY)METHYL]PYRROLIDINE HYDROCHLORIDE; 2 [(2,3 DICHLOROPHENOXY)METHYL]PYRROLIDINE; 2 [(2,3 DICHLOROPHENOXY)METHYL]PYRROLIDINE HYDROCHLORIDE; ALIPHATIC AMINE; ANALGESIC AGENT; N METHYL 1 (1 NAPHTHYLOXY)PROPAN 1 AMINE; N METHYL 1 (1 NAPHTHYLOXY)PROPAN 2 AMINE HYDROCHLORIDE; N METHYL 2 (1 NAPHTHYLOXY)ETHANAMINE; N METHYL 2 (1 NAPHTHYLOXY)PROPAN 1 AMINE; N METHYL 2 (1 NAPHTHYLOXY)PROPAN 1 AMINE HYDROCHLORIDE; NICOTINIC RECEPTOR; SEROTONIN 1B RECEPTOR; SEROTONIN 1D RECEPTOR; SEROTONIN AGONIST; SUMATRIPTAN; UNCLASSIFIED DRUG;

ANALGESIC ACTIVITY; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; ASSAY; BINDING AFFINITY; BRAIN MEMBRANE; CONTROLLED STUDY; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG SYNTHESIS; GUINEA PIG; HOT PLATE TEST; MALE; MOUSE; NONHUMAN; PRIORITY JOURNAL;

AMINES; ANALGESICS; ANIMALS; MICE; RECEPTOR, SEROTONIN, 5-HT1B; RECEPTOR, SEROTONIN, 5-HT1D; STEREOISOMERISM; TRYPTAMINES;

EID: 77951669435     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.200900530     Document Type: Article

References (48)

1. N. M. Barnes, T. Sharp, Neuropharmacology 1999, 38, 1083-1152.
2. D. Hoyer, J. P. Hannon, G. R. Martin, Pharmacol. Biochem. Behav. 2002, 71, 533-554.
3. F. G. Boess, I. L. Martin, Neuropharmacology 1994, 33, 275-317.
4. D. Hoyer, D. E. Clarke, J. R. Fozard, P. R. Hartig, G. R. Martin, E. J. Mylecharane, P. R. Saxena, P. P. Humphrey, Pharmacol. Rev. 1994, 46, 157-203.
5. P. R. Hartig, D. Hoyer, P. P. A. Humprey, G. R. Martin, Trends Pharmacol. Sci. 1996, 17, 103-105.
6. M. W. Hamblin, M. A. Metcalf, Mol. Pharmacol. 1991, 40, 143-148.
7. H. Jin, D. Oksenberg, A. Ashkenazi, S. J. Peroutka, A. M. Duncan, R. Rozmahel, Y. Yang, G. Mengod, J. M. Palacios, B. F. O'Dowd, J. Biol. Chem. 1992, 267, 5735-5738.
8. I. Bouchelet, Z. Cohen, B. Case, P. Séguela, E. Hamel, Mol. Pharmacol. 1996, 50, 219-223.
9. P. J. Goadsby, Trends Mol. Med. 2007, 13, 39-44.
10. I. Szelenyi, Drug News Perspect. 1989, 2, 45-49.
11. J. A. Lopez-Garcia, Curr. Top. Med. Chem. 2006, 6, 1987-1996.
12. R. D. Jeggo, Y. Wang, D. Jordan, A. G. Ramage, Br. J. Pharmacol. 2007, 150, 987-995.
13. E. Hamel, Serotonin 1996, 1, 19-29.
14. A. Ferro, J. Longmore, R. G. Hill, M. J. Brown, Br. J. Clin. Pharmacol. 1995, 40, 245-251.
15. J. Longmore, C. M. Boulanger, B. Desta, R. G. Hill, W. N. Schofield, A. A. Taylor, Br. J. Clin. Pharmacol. 1996, 42, 431-441.
16. P. P. A. Humphrey, P. J. Goadsby, Cephalalgia 1994, 14, 401-410.
17. M. Wilkinson, V. Pfaffenrath, J. Schoenen, H.-C. Diener, T. J. Steiner, Cephalalgia 1995, 15, 337-357.
18. A. M. Ismaiel, M. Dukat, H. Law, R. Kamboj, E. Fan, D. K. H. Lee, L. Mazzocco, D. Buekschkens, M. Teitler, M. E. Pierson, R. A. Glennon, J. Med. Chem. 1997, 40, 4415-4419.
19. M. Bondarev, T. Iwamura, D. Hynd, L. Mazzocco, D. K. Lee, M. Dukat, R. A. Glennon, Med. Chem. Res. 1998, 8, 333-342.
20. F. Sternfeld, A. R. Guiblin, R. A. Jelley, V. G. Matassa, A. J. Reeve, P. A. Hunt, M. S. Beer, A. Heald, J. A. Stanton, B. Sohal, A. P. Watt, L. J. Street, J. Med. Chem. 1999, 42, 677-690.
21. R. C. Glen, G. R. Martin, A. P. Hill, R. M. Hyde, P. M. Woollard, J. A. Salmon, J. Buckingham, A. D. Robertson, J. Med. Chem. 1995, 38, 3566-3580.
22. G. Van Lommen, M. De Bruyn, M. Schroven, W. Verschueren, W. Janssens, J. Verrelst, J. Leysen, Bioorg. Med. Chem. Lett. 1995, 5, 2649-2654.
23. O. Mitsunobu, Synthesis 1981, 1-28.
24. A. Carocci, A. Catalano, F. Corbo, A. Duranti, R. Amoroso, C. Franchini, G. Lentini, V. Tortorella, Tetrahedron: Asymmetry 2000, 11, 3619-3634.
25. E. Roubini, R. Laufer, C. Gilon, Z. Selinger, B. P. Roques, M. Cohrev, J. Med. Chem. 1991, 34, 2430-2438.
26. P. Depreux, D. Lesieur, H. A. Mansour, P. Morgan, H. E. Howell, P. Renard, D.-H. Caignard, B. Pfeiffer, P. Delagrange, B. Guardiola, S. Yous, A. Demarque, G. Adam, J. Andrieux, J. Med. Chem. 1994, 37, 3231-3239.
27. D. Rance, N. Clear, L. Dallman, E. Llewellyn, J. Nuttall, H. Verrier, Headache [abstract] 1997, 37, 328.
28. T. A. Barf, P. de Boer, H. Wikstrçm, J. Med. Chem. 1996, 39, 4717-4726.
29. M. Leopoldo, E. Lacivita, P. De Giorgio, C. Fracasso, S. Guzzetti, S. Caccia, M. Contino, N. A. Colabufo, F. Berardi, R. Perrone, J. Med. Chem. 2008, 51, 5813-5822.
30. R. L. Elliott, H. Kopecka, D. E. Gunn, N. H. Lin, D. S. Garvey, K. B. Ryther, M. W. Holladay, D. J. Anderson, J. E. Campbell, J. P. Sullivan, M. J. Buckley, K. L. Gunther, A. B. O'Neill, M. W. Decker, S. P. Arneric', Bioorg. Med. Chem. Lett. 1996, 6, 2283-2288.
31. M. Williams, E. A. Kowaluk, S. P. Arneric, J. Med. Chem. 1999, 42, 1481-1500.
32. A. Carocci, A. Duranti, G. Lentini, N. Tangari, B. Stankov, V. Lucini, R. Nonno, F. Fraschini, V. Tortorella, Book of Abstracts, Italian Chemical Society (SCI) Meeting, Torino (Italy), September 1997, A15.
33. T. Anger, D. J. Madge, M. Mulla, D. Riddall, J. Med. Chem. 2001, 44, 115-137.
34. R. K. Portenoy, J. Pain Symptom Manage. 2000, 19 (Suppl. 1), 16-20.
35. K. Huang, M. Ortiz-Marciales, V. Stepanenko, M. De Jesùs, W. Correa, J. Org. Chem. 2008, 73, 6928-6931.
36. D. G. Loughhead, L. A. Flippin, R. J. Weikert, J. Org. Chem. 1999, 64, 3373-3375.
37. K. Kingwell, Nat. Rev. Drug Discovery 2009, 8, 931.
38. F. Lovering, J. Bikker, C. Humblet, J. Med. Chem. 2009, 52, 6752-6756.
39. G. Carbonara, A. Carocci, G. Fracchiolla, C. Franchini, G. Lentini, F. Loiodice, P. Tortorella, ARKIVOC 2004, Part (v), 5-25.
40. W. C. Still, M. Kahn, A. Mitra, J. Org. Chem. 1978, 43, 2923-2925.
41. J. E. Comer, K. Y. Tam in Pharmacokinetic Optimization in Drug Research (Eds.: B. Testa, H. van de Waterbeemd, G. Folkers, R. H. Guy), Wiley-VCH, Weinheim, 2001, pp. 275-304.
42. A. Avdeef, Quant. Struct.-Act. Relat. 1992, 11, 510-517.
43. A. Avdeef, J. Pharm. Sci. 1993, 82, 183-190.
44. A. Avdeef in Lipophilicity in Drug Action and Toxicology (Eds.: V. Pilška, B. Testa, H. van de Waterbeemd), VCH Publishers, Weinheim, 1996, pp. 109-139.
45. A. Avdeef, K. J. Box, J. E. Comer, M. Gilges, M. Hadley, C. Hibbert, W. Patterson, K. Y. Tam, J. Pharm. Biomed. Anal. 1999, 20, 631-641.
46. V. Audinot, S. Lochon, A. Newman-Tancredi, G. Lavielle, M. J. Millan, Eur. J. Pharmacol. 1997, 327, 247-256.
47. J. Ji, W. H. Bunnelle, D. J. Anderson, C. Faltynek, T. Dyhring, P. K. Ahring, L. E. Rueter, P. Curzon, M. J. Buckley, K. C. Marsh, A. Kempf-Grote, M. D. Meyer, Biochem. Pharmacol. 2007, 74, 1253-1262.
48. J. P. O'Callaghan, S. G. Holtzman, J. Pharmacol. Exp. Ther. 1976, 197, 533-544.