Synthesis and structure-activity relationships of new carbonyl guanidine derivatives as novel dual 5-HT2B and 5-HT7 receptor antagonists

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 24, 2013, Pages 7841-7852

  Moritomo, Ayako ^a   Yamada, Hiroyoshi ^a   Watanabe, Toshihiro ^a   Itahana, Hirotsune ^a   Akuzawa, Shinobu ^a   Okada, Minoru ^a   Ohta, Mitsuaki ^a  

^a ASTELLAS PHARMA INC   (Japan)

Author keywords

5 HT2B receptor; 5 HT7 receptor; Carbonyl guanidine; Dual antagonist; Migraine

Indexed keywords

10H PHENOXAZINE 2 CARBONITRILE; 10H PHENOXAZINE 2 CARBOXYLIC ACID; 3 [2 [2 (4 METHYL 1 PIPERIDINYL)ETHYL] 1 PYRROLIDINESULFONYL]PHENOL; 4 (2 AMINOPHENOXY) 3 FLUOROBENZONITRILE; 9 OXO 9H FLUORENE 3 CARBOXYLIC ACID; CARBONYLGUANIDINE DERIVATIVE; DIBENZO[B,D]FURAN 3 CARBOXYLIC ACID; GUANIDINE DERIVATIVE; METHYL 3 (2 FORMYLPHENOXY)BENZOATE; METHYL 3 (2 TRIFLUOROMETHANESULFONATE)BENZOATE; METHYL 9H CARBAZOLE 2 CARBOXYLATE; N (9 HYDROXY 9H FLUORENE 2 CARBONYL)GUANIDINE; N (9 HYDROXY 9H FLUORENE 3 CARBONYL)GUANIDINE; N (9 OXO 9H FLUORENE 3 CARBONYL)GUANIDINE; N (9H FLUORENE 1 CARBONYL)GUANIDINE; N (9H FLUORENE 4 CARBONYL)GUANIDINE; N (DIAMINOMETHYLENE) 10H PHENOXAZINE 2 CARBOXAMIDE; N (DIAMINOMETHYLENE) 10H PHENOXAZINE 3 CARBOXAMIDE; N (DIAMINOMETHYLENE) 3 (9 HYDROXY 9H FLUOREN 2 YL)ACRYLAMIDE; N (DIAMINOMETHYLENE) 3 (9 OXO 9H FLUOREN 2 YL)ACRYLAMIDE; N (DIAMINOMETHYLENE) 9 OXO 9H FLUORENE 2 CARBOXAMIDE; N (DIAMINOMETHYLENE) 9H CARBAZOLE 2 CARBOXAMIDE; N (DIAMINOMETHYLENE) 9H FLUORENE 2 CARBOXAMIDE; N (DIAMINOMETHYLENE)DIBENZO[B,D]FURAN 3 CARBOXAMIDE; PIZOTIFEN; RS 127445; SEROTONIN 2B RECEPTOR; SEROTONIN 7 RECEPTOR; SEROTONIN ANTAGONIST; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; DOSE RESPONSE; DRUG IDENTIFICATION; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; EMBRYO; GUINEA PIG; HIGH THROUGHPUT SCREENING; HUMAN; HUMAN CELL; IN VITRO STUDY; MALE; MOLECULAR MODEL; NONHUMAN; RECEPTOR AFFINITY; SINGLE DRUG DOSE; STRUCTURE ACTIVITY RELATION;

CAVIA;

5-HT(2B) RECEPTOR; 5-HT(7) RECEPTOR; CARBONYL GUANIDINE; DUAL ANTAGONIST; MIGRAINE;

DOSE-RESPONSE RELATIONSHIP, DRUG; GUANIDINE; HUMANS; MOLECULAR STRUCTURE; RECEPTOR, SEROTONIN, 5-HT2B; RECEPTORS, SEROTONIN; SEROTONIN ANTAGONISTS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84888430545     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2013.10.010     Document Type: Article

References (41)

1. M.A. Moskowitz Ann. Neurol. 16 1984 157
2. G. Hirose Nihon Naika Gakkai Zasshi 90 2001 595
3. D.S. Stephen Headache 34 1994 408
4. S. Mehrotra, S. Gupta, K.Y. Chan, C.M. Villalón, D. Centurión, P.R. Saxena, and A. MaassenVanDenBrink Naunyn Schmiedebergs Arch. Pharmacol. 378 2008 371
5. K.W. Johnson, L.A. Phebus, M.L. Cohen, and E. Jucker Prog. Drug Res. 51 1998 219
6. E.J. Mylecharane J. Neurol. 238 1991 S45
7. J. Arnt, J. Hyttel, and J.J. Larsen Acta Pharm. Toxicol. 55 1984 363
8. J.E. Leysen, F. Awouters, L. Kennis, P.M. Laduron, J. Vandenberk, and P.A.J. Janssen Life Sci. 28 1981 1015
9. A. Newman-Tancredi, C. Conte, C. Chaput, L. Verriele, V. Audinot-Bouchez, S. Lochon, G. Lavielle, and M.J. Millan Naunyn Schmiedebergs Arch. Pharmacol. 355 1997 682
10. K.W. Johnson, D.L. Nelson, D.K. Dieckman, D.B. Wainscott, V.L. Lucaites, J.E. Audia, W.M. Owton, and L.A. Phebus Cephalalgia 23 2003 117
11. P. Manivet, S. Mouillet-Richard, J. Callebert, C.G. Nebigil, L. Maroteaux, S. Hosoda, O. Kellermann, and J.-M. Launay J. Biol. Chem. 275 2000 9324
12. E.P. Wei, M.A. Moskowitz, P. Boccalini, and H.A. Kontos Circ. Res. 70 1992 1313
13. D.W. Bonhaus, L.A. Flippin, R.J. Greenhouse, S. Jaime, C. Rocha, M. Dawson, K.V. Natta, L.K. Chang, T. Pulido-Rios, A. Webber, E. Leung, R.M. Eglen, and G.R. Martin Br. J. Pharmacol. 127 1999 1075
14. G. Poissonnet, J.G. Parmentier, J.A. Boutin, and S. Goldstein Mini Rev Mini-Rev. Med. Chem. 4 2004 325
15. J.A. Terrón, I. Bouchelet, and E. Hamel Neurosci. Lett. 302 2001 9
16. J.A. Terrón Eur. J. Pharmacol. 439 2002 1
17. P.A. Pierce, G.-X. Xie, S.J. Peroutka, and J.D. Levine Region. Anesth. 21 1996 219
18. P.J. Lovell, S.M. Bromidge, S. Dabbs, D.M. Duckworth, I.T. Forbes, A.J. Jennings, F.D. Kings, D.N. Middlemiss, S.K. Rahman, D.V. Saunder, L.L. Collin, J.J. Hagan, G.J. Riley, and D.R. Thomans J. Med. Chem. 43 2000 342
19. X. Wang, Y. Fang, J. Liang, Z. Yin, J. Mian, and N. Luo Headache 50 2010 579
20. C. Ullmer, K. Schmuck, H.O. Kalkman, and H. Lübbert FEBS Lett. 370 1995 215
21. Akuzawa, S.; Watanabe, T. WO 2,005,079,845.
22. Yamada, H.; Itahana, H.; Moritomo, A.; Matsuzawa, T.; Harada, K.; Fujiyasu, J.; Koga, Y.; Oku, M.; Okazaki, T.; Akuzawa, S. WO 2,005,080,322.
23. J.H. Weisburger J. Org. Chem. 23 1958 1193
24. G.N. Koshel, P. Magagnini, S.G. Koshel, N.V. Lebedeva, M.V. Postnova, V.G. Kulichikhin, and A.Y. Bilibin Russ. J. Org. Chem. 37 2001 830
25. C.W. Holzapfel, and C. Dwyer Heterocycles 48 1998 1513
26. G.C. Eastmond, T.L. Glichrist, J. Paprotny, and A. Steiner New J. Chem. 25 2001 385
27. C. Hansch, J.E. Quinlan, and G.L. Lawrence J. Org. Chem. 33 1968 347
28. S.C. Valvani, S.H. Yalkowsky, and T.J. Roseman J. Pharm. Sci. 70 1981 502
29. J. Ali, P. Camilleri, M.B. Brown, A.J. Hutt, and S.B. Kirton J. Chem. Inf. Model. 52 2012 2950
30. ACD/Labs version 12.01; Advanced Chemistry Development: Toronto, Canada.
31. Molecular Operating Environment (MOE), 2011.10; Chemical Computing Group: 1010 Sherbooke St. West, Suite #910, Montreal, QC, Canada, H3A 2R7, 2011.
32. M.L. Connolly J. Appl. Crystallogr. 16 1983 548
33. K. Schmuck, C. Ullmer, P. Engels, and H. Lübbert FEBS Lett. 342 1994 85
34. Y.C. Cheng, and W.H. Prussoff Biochem. Pharmacol. 22 1973 3099
35. J.A. Bard, J. Zgombick, N. Adham, P. Vaysse, T.A. Branchek, and R.L. Weinshank J. Biol. Chem. 268 1993 23422
36. J.R. Jasper, A. Kosaka, Z.P. To, D.J. Chang, and R.M. Eglen Br. J. Pharmacol. 122 1997 126
37. J.E. Leysen, C.J.E. Niemegeers, J.M.V. Nueten, and P.M. Laduron Mol. Pharmacol. 21 1982 301
38. M.C. Michel, O.-E. Brodde, B. Schnepel, J. Behrendt, R. Tschada, H.J. Motulsky, and P.A. Insel Mol. Pharmacol. 35 1989 324
39. L.T. Potter, C.A. Ferrendelli, and H.E. Hanchett Cell. Mol. Neurol. 8 1988 181
40. M. Terai, K. Hidaka, and Y. Nakamura Eur. J. Pharmacol. 173 1989 177
41. R.A. Spokes, and V.C. Middlefell Eur. J. Phamacol. 281 1995 75