Fluoro-substituted phenylazocarboxamides: Dopaminergic behavior and N-arylating properties for irreversible binding

Bioorganic and Medicinal Chemistry

Volumn 23, Issue 14, 2015, Pages 3938-3947

  Bartuschat, Amelie L ^a   Schellhorn, Tamara ^a   Hübner, Harald ^a   Gmeiner, Peter ^a   Heinrich, Markus R ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

Azocarboxamide; Bioisosteres; Covalent ligands; D3< inf> receptor; Dopamine; GPCR

Indexed keywords

2 (3,4 DIFLUOROPHENYL) N [2 [(2,3 DIHYDRO 1H INDEN 2 YL)(PROP 1 YL)AMINO]ETHYL]DIAZENE 1 CARBOXAMIDE; 2 (3,4 DIFLUOROPHENYL) N [4 [(2,3 DIHYDRO 1H INDEN 2 YL)(PROP 1 YL)AMINO]BUTYL]DIAZENE 1 CARBOXAMIDE; 2 (3,4 DIFLUOROPHENYL) N [4 [4 (2 METHOXYPHENYL)PIPERAZIN 1 YL]BUTYL]DIAZENE 1 CARBOXAMIDE; AMIDE; DOPAMINE 3 RECEPTOR BLOCKING AGENT; DOPAMINE 3 RECEPTOR STIMULATING AGENT; N [2 [(2,3 DIHYDRO 1H INDEN 2 YL)(PROP 1 YL)AMINO]ETHYL] 2 (3,4,5 TRIFLUOROPHENYL)DIAZENE 1 CARBOXAMIDE; N [2 [(2,3 DIHYDRO 1H INDEN 2 YL)(PROP 1 YL)AMINO]ETHYL] 2 (4 FLUOROPHENYL)DIAZENE 1 CARBOXAMIDE; N [2 [(2,3 DIHYDRO 1H INDEN 2 YL)(PROP 1 YL)AMINO]ETHYL] 3 (4 FLUOROPHENYL)ACRYLAMIDE; N [4 [(2,3 DIHYDRO 1H INDEN 2 YL)(PROP 1 YL)AMINO]BUTYL] 2 (3,4,5 TRIFLUOROPHENYL)DIAZENE 1 CARBOXAMIDE; N [4 [(2,3 DIHYDRO 1H INDEN 2 YL)(PROP 1 YL)AMINO]BUTYL] 2 (4 FLUOROPHENYL)DIAZENE 1 CARBOXAMIDE; N [4 [(2,3 DIHYDRO 1H INDEN 2 YL)(PROP 1 YL)AMINO]BUTYL] 3 (4 FLUOROPHENYL)ACRYLAMIDE; N [4 [4 (2 METHOXYPHENYL)PIPERAZIN 1 YL]BUTYL] 2 (3,4,5 TRIFLUOROPHENYL)DIAZENE 1 CARBOXAMIDE; PHENYLAZOCARBOXAMIDE DERIVATIVE; UNCLASSIFIED DRUG; DOPAMINE 3 RECEPTOR; FLUORINE; GLUTAMIC ACID; LIGAND; LYSINE;

ANIMAL CELL; ARTICLE; ARYLATION; BINDING AFFINITY; CHEMICAL MODIFICATION; CONCENTRATION RESPONSE; CONTROLLED STUDY; COVALENT BOND; DOPAMINERGIC ACTIVITY; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; EC50; HUMAN; HUMAN CELL; INCUBATION TIME; LIGAND BINDING; MEDICINAL CHEMISTRY; NONHUMAN; PHYSICAL CHEMISTRY; REACTION ANALYSIS; AGONISTS; ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; GENETICS; HEK293 CELL LINE; METABOLISM; MUTATION; PRECLINICAL STUDY; PROCEDURES; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

AMIDES; CHEMISTRY TECHNIQUES, SYNTHETIC; DRUG EVALUATION, PRECLINICAL; FLUORINE; GLUTAMIC ACID; HEK293 CELLS; HUMANS; LIGANDS; LYSINE; MOLECULAR STRUCTURE; MUTATION; RECEPTORS, DOPAMINE D3; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84931275605     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2014.12.012     Document Type: Article

References (76)

1. M. Pilla, S. Perachon, F. Sautel, F. Garrido, A. Mann, C.G. Wermuth, J.C. Schwartz, B.J. Everitt, and P. Sokoloff Nature 400 1999 371
2. J.N. Joyce Pharmacol. Ther. 90 2001 231
3. T. Kienast, and A. Heinz CNS Neurol. Disord.: Drug Targets 5 2006 109
4. A.E. Hackling, and H. Stark ChemBioChem 3 2002 946
5. P. Sokoloff, J. Diaz, B. Le Foll, O. Guillin, L. Leriche, E. Bezard, and C. Gross CNS Neurol. Disord.: Drug Targets 5 2006 25
6. F. Boeckler, and P. Gmeiner Pharmacol. Ther. 112 2006 281
7. A. Zhang, J.L. Neumeyer, and R.J. Baldessarini Chem. Rev. 107 2007 274
8. O. Prante, S. Maschauer, and A. Banerjee J. Labelled Comp. Radiopharm. 56 2013 130
9. L. Herroelen, J.P. Debacker, N. Wilczak, A. Flamez, G. Vauquelin, and J. Dekeyser Brain Res. 648 1994 222
10. P. Sokoloff, and J.C. Schwartz Trends Pharmacol. Sci. 16 1995 270
11. A.H. Newman, P. Grundt, and M.A. Nader J. Med. Chem. 48 2005 3663
12. S. Löber, H. Hübner, N. Tschammer, and P. Gmeiner Trends Pharmacol. Sci. 32 2011 148
13. P. Sokoloff, B. Giros, M.P. Martres, M.L. Bouthenet, and J.C. Schwartz Nature 347 1990 146
14. A.E. Hackling, R. Ghosh, S. Perachon, A. Mann, H.D. Holtje, C.G. Wermuth, J.C. Schwartz, W. Sippl, P. Sokoloff, and H. Stark J. Med. Chem. 46 2003 3883
15. W.H. Chu, Z. Tu, E. McElveen, J.B. Xu, M. Taylor, R.R. Luedtke, and R.H. Mach Bioorg. Med. Chem. 13 2005 77
16. M. Leopoldo, E. Lacivita, N.A. Colabufo, F. Berardi, and R. Perrone J. Pharm. Pharmacol. 58 2006 209
17. K. Schlotter, F. Boeckler, H. Hübner, and P. Gmeiner J. Med. Chem. 49 2006 3628
18. P. Grundt, K.M. Prevatt, J.J. Cao, M. Taylor, C.Z. Floresca, J.K. Choi, B.G. Jenkins, R.R. Luedtke, and A.H. Newman J. Med. Chem. 50 2007 4135
19. N. Tschammer, J. Elsner, A. Goetz, K. Ehrlich, S. Schuster, M. Ruberg, J. Kühhorn, D. Thompson, J. Whistler, H. Hübner, and P. Gmeiner J. Med. Chem. 54 2011 2477
20. D. Möller, R.C. Kling, M. Skultety, K. Leuner, H. Hübner, and P. Gmeiner J. Med. Chem. 57 2014 4861
21. L. Bettinetti, K. Schlotter, H. Hübner, and P. Gmeiner J. Med. Chem. 45 2002 4594
22. O. Saur, A.E. Hackling, S. Perachon, J.-C. Schwartz, P. Sokoloff, and H. Stark Arch. Pharm. 340 2007 178
23. A. Böcker, B.C. Sasse, M. Nietert, H. Stark, and G. Schneider ChemMedChem 2 2007 1000
24. S.B. Höfling, S. Maschauer, H. Hübner, P. Gmeiner, H.J. Wester, O. Prante, and M.R. Heinrich Bioorg. Med. Chem. Lett. 20 2010 6933
25. For the most important 11C-labeled D3 receptor ligand, napththoxazine [11C](+)-PHNO, see: A. Graff-Guerrero, M. Willeit, N. Ginovart, D. Mamo, R. Mizrahi, P. Rusjan, I. Vitcu, P. Seeman, A.A. Wilson, and S. Kapur Hum. Brain Mapp. 29 2008 400
26. A.A. Wilson, P. McCormick, S. Kapur, M. Willeit, A. Garcia, D. Hussey, S. Houle, P. Seeman, and N. Ginovart J. Med. Chem. 48 2005 4153
27. R.H. Mach, Z. Tu, J. Xu, S. Li, L.A. Jones, M. Taylor, R.R. Luedtke, C.P. Derdeyn, J.S. Perlmutter, and M.A. Mintun Synapse 65 2011 724
28. C. Hocke, S. Maschauer, H. Hübner, S. Löber, W. Utz, T. Kuwert, P. Gmeiner, and O. Prante ChemMedChem 5 2010 941
29. C. Hocke, O. Prante, S. Löber, H. Hübner, P. Gmeiner, and T. Kuwert Bioorg. Med. Chem. Lett. 15 2005 4819
30. C. Hocke, O. Prante, I. Salama, H. Hübner, S. Löber, T. Kuwert, and P. Gmeiner ChemMedChem 3 2008 788
31. C. Hocke, P. Cumming, S. Maschauer, T. Kuwert, P. Gmeiner, and O. Prante Nucl. Med. Biol. 41 2014 223
32. I. Salama, C. Hocke, W. Utz, O. Prante, F. Boeckler, H. Hübner, T. Kuwert, and P. Gmeiner J. Med. Chem. 50 2007 489
33. S.K. Fehler, S. Maschauer, S.B. Höfling, A.L. Bartuschat, N. Tschammer, H. Hübner, P. Gmeiner, O. Prante, and M.R. Heinrich Chem. Eur. J. 20 2014 370
34. S.B. Höfling, A.L. Bartuschat, and M.R. Heinrich Angew. Chem., Int. Ed. 49 2010 9769
35. H. Jasch, S. Höfling, and M.R. Heinrich J. Org. Chem. 77 2012 1520
36. Unpublished results.
37. For reviews covalent ligand binding, see: G. Dormán, and G.D. Prestwich Trends Biotechnol. 18 2000 64
38. E.L. Vodovozova Biochemistry (Mosc.) 72 2007 1
39. A. Sinz Angew. Chem., Int. Ed. 46 2007 660
40. P.J. Weber, and A.G. Beck-Sickinger J. Pept. Res. 49 1997 375
41. G.-L. Chee, J.C. Yalowich, A. Bodner, X. Wu, and B.B. Hasinoff Bioorg. Med. Chem. 18 2010 830
42. M.R. Bond, H. Zhang, P.D. Vu, and J.J. Kohler Nat. Protoc. 4 2009 1044
43. J.R. Lever, M.F. Zou, M.L. Parnas, R.A. Duval, S.E. Wirtz, J.B. Justice, R.A. Vaughan, and A.H. Newman Bioconj. Chem. 16 2005 644
44. A. Beaumont, J.F. Hernandez, P. Chaillet, P. Crine, and B.P. Roques Mol. Pharmacol. 32 1987 594
45. W. Wouters, J. van Dun, and P.M. Laduron Eur. J. Biochem. 145 1984 273
46. J.M. Belanger, Y. Raviv, M. Viard, M.J. de la Cruz, K. Nagashima, and R. Blumenthal Virology 417 2011 221
47. K. Pleban, S. Kopp, E. Csaszar, M. Peer, T. Hrebicek, A. Rizzi, G.F. Ecker, and P. Chiba Mol. Pharmacol. 67 2005 365
48. D. Weichert, A.C. Kruse, A. Manglik, C. Hiller, C. Zhang, H. Hübner, B.K. Kobilka, and P. Gmeiner Proc. Natl. Acad. Sci. U.S.A. 111 2014 10744
49. E. Buck, and J.A. Wells Proc. Natl. Acad. Sci. U.S.A. 102 2005 2719
50. E. Buck, H. Bourne, and J.A. Wells J. Biol. Chem. 280 2005 4009
51. See also Ref. 34.
52. J. Milecki, S.P. Baker, K.M. Standifer, T. Ishizu, Y. Chida, J.W. Kusiak, and J. Pitha J. Med. Chem. 30 1987 1563
53. S. Nijmeijer, H. Engelhardt, S. Schultes, A.C. van de Stolpe, V. Lusink, C. de Graaf, M. Wijtmans, E.E. Haaksma, I.J. de Esch, K. Stachurski, H.F. Vischer, and R. Leurs Br. J. Pharmacol. 170 2013 89
54. A. Manglik, A.C. Kruse, T.S. Kobilka, F.S. Thian, J.M. Mathiesen, R.K. Sunahara, L. Pardo, W.I. Weis, B.K. Kobilka, and S. Granier Nature 485 2012 321
55. F. Sanger Biochem. J. 39 1945 507
56. H.N. Eisen, S. Belman, and M.E. Carston J. Am. Chem. Soc. 75 1953 4583
57. D. Crich, and I. Sharma Angew. Chem., Int. Ed. 48 2009 2355
58. J.Y. Hwang, W. Huang, L.A. Arnold, R. Huang, R.R. Attia, M. Connelly, J. Wichterman, F. Zhu, I. Augustinaite, C.P. Austin, J. Inglese, R.L. Johnson, and R.K. Guy J. Biol. Chem. 286 2011 11895
59. N. Tschammer, M. Doerfler, H. Huebner, and P. Gmeiner ACS Chem. Neurosci. 1 2010 25
60. G. Hayes, T.J. Biden, L.A. Selbie, and J. Shine Mol. Endocrinol. 6 1992 920
61. P. Sokoloff, M. Andrieux, R. Besançon, C. Pilon, M.-P. Martres, B. Giros, and J.-C. Schwartz Eur. J. Pharmacol. 225 1992 331
62. V. Asghari, S. Sanyal, S. Buchwaldt, A. Paterson, V. Jovanovic, and H.H.M. Van Tol J. Neurochem. 65 1995 1157
63. H. Hübner, C. Haubmann, W. Utz, and P. Gmeiner J. Med. Chem. 43 2000 756
64. The synthesis of the cinnamic acid amides 1, 16, 17 used as reference compounds was achieved through coupling of the respective cinnamic acid chloride to amines 12-14. For a detailed procedure, see Ref. 9.
65. Attempts with the difluorinated ligand 6 revealed a too low reactivity of the aromatic core for reactions with primary aliphatic amines.
66. The hydrolyzed derivative (free carboxylic acid) of 19 was obtained as side product. Control experiments showed that the nucleophilic substitution can be accelerated by the addition of DMSO to the PBS buffer solution.
67. D.M. Rosenbaum, C. Zhan, J.A. Lyons, R. Holl, D. Aragao, D.H. Arlow, S.G.F. Rasmussen, H.-J. Choi, B.T. DeVree, R.K. Sunahara, P.S. Chae, S.H. Gellman, R.O. Dror, D.E. Shaw, W.I. Weis, M. Caffrey, P. Gmeiner, and B.K. Kobilka Nature 469 2011 236
68. A.C. Kruse, A.M. Ring, A. Manglik, J. Hu, K. Hu, K. Eitel, H. Hübner, E. Pardon, C. Valant, P.M. Sexton, A. Christopoulos, C.C. Felder, P. Gmeiner, J. Steyaert, W.I. Weis, K.C. Garcia, J. Wess, and B.K. Kobilka Nature 504 2013 101
69. H. Jasch, J. Scheumann, and M.R. Heinrich J. Org. Chem. 77 2012 10699
70. J. Hofmann, H. Jasch, and M.R. Heinrich J. Org. Chem. 79 2014 2314
71. Bentley, J. M.; Roffey, J. R. A.; Davidson, E. P.; Mansell, H. L.; Hamlyn, R. J.; Adams, I. D. R.; Monck, N. J.; U.S. 006706750B1, 2004.
72. M. Jordan, A. Schallhorn, and F.M. Wurm Nucleic Acids Res. 24 1996 596
73. O.H. Lowry, N.J. Rosebrough, A.L. Farr, and R.J. Randall J. Biol. Chem. 193 1951 265
74. Y. Cheng, and W.H. Prusoff Biochem. Pharmacol. 22 1973 3099
75. M. Dörfler, N. Tschammer, K. Hamperl, H. Hübner, and P. Gmeiner J. Med. Chem. 51 2008 6829
76. E. Kostenis, L. Martini, J. Ellis, M. Waldhoer, A. Heydorn, M.M. Rosenkilde, P.K. Norregaard, R. Jorgensen, J.L. Whistler, and G. Milligan J. Pharmacol. Exp. Ther. 313 2005 78