Fancy bioisosteres: Metallocene-derived G-protein-coupled receptor ligands with subnanomolar binding affinity and novel selectivity profiles

Journal of Medicinal Chemistry

Volumn 48, Issue 11, 2005, Pages 3696-3699

  Schlotter, Karin ^a   Boeckler, Frank ^a   Hübner, Harald ^a   Gmeiner, Peter ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2 DIPROPYLAMINO 8 HYDROXYTETRALIN; 8 CHLORO 2,3,4,5 TETRAHYDRO 3 METHYL 5 PHENYL 1H 3 BENZAZEPIN 7 OL HYDROGEN MALEATE; AMIDE; BP 897; CENTRAL NERVOUS SYSTEM AGENTS; DOPAMINE 3 RECEPTOR; DOPAMINE 4 RECEPTOR; DOPAMINE RECEPTOR STIMULATING AGENT; FAUC 378; FAUC 413; FERROCENE DERIVATIVE; FERROCENYLCARBOXAMIDE DERIVATIVE; G PROTEIN COUPLED RECEPTOR; KETANSERIN; LIGAND; METAL DERIVATIVE; PRAZOSIN; QUINPIROLE; RUTHENOCENE DERIVATIVE; SEROTONIN RECEPTOR; SPIPERONE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; BIOISOSTERE; CENTRAL NERVOUS SYSTEM; CHEMICAL STRUCTURE; CONTROLLED STUDY; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; NONHUMAN; PLASTICITY; RADIOASSAY;

ANIMALS; BINDING SITES; BINDING, COMPETITIVE; CHO CELLS; CRICETINAE; CRICETULUS; CYCLOPENTANES; FERROUS COMPOUNDS; GUANOSINE 5'-O-(3-THIOTRIPHOSPHATE); LIGANDS; MITOSIS; MODELS, MOLECULAR; ORGANOMETALLIC COMPOUNDS; RADIOLIGAND ASSAY; RECEPTOR, SEROTONIN, 5-HT1A; RECEPTORS, DOPAMINE D2; RECEPTORS, DOPAMINE D3; RECEPTORS, DOPAMINE D4; RECEPTORS, G-PROTEIN-COUPLED; RUTHENIUM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 20144375764     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm050170s     Document Type: Article

References (32)

1. Chen, X.; Wang, W. The use of bioisosteric groups in lead optimization. Annu. Rep. Med. Chem. 2003, 35, 333-346.
2. (a) Bettinetti, L.; Schlotter, K.; Hübner, H.; Gmeiner, P. Interactive SAR studies: rational discovery of super-potent and highly selective dopamine D3 receptor antagonists and partial agonists. J. Med. Chem. 2002, 45, 4594-4597.
3. (b) Boeckler, F.; Leng, A.; Mura, A. Bettinetti, L.; Feldon, J.; Gmeiner, P.; Ferger, B. Attenuation of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) neurotoxicity by the novel selective dopamine D3-receptor partial agonist FAUC 329 predominantly in the nucleus accumbens of mice. Biochem. Pharmacol. 2003, 66, 1025-1032.
4. (a) Löber, S.; Hübner, H.; Utz, W.; Gmeiner, P. Rationally based efficacy tuning of selective dopamine D4 receptor ligands leading to the complete antagonist 2-[4-(4-chlorophenyl)piperazin-1-ylmethyl]pyrazolo[1,5-a] pyridine (FAUC 213). J. Med. Chem. 2001, 44, 2691-2694.
5. (b) Boeckler, F.; Russig, H.; Zhang, W.; Löber, S.; Schetz, J.; Hübner, H.; Ferger, B.; Gmeiner, P.; Feldon, J. FAUC 213, a highly selective dopamine D4 receptor full antagonist, exhibits atypical antipsychotic properties in behavioural and neurochemical models of schizophrenia. Psychopharmacology (Berlin) 2004, 175, 7-17.
6. (a) Hübner, H.; Haubmann, C.; Utz, W.; Gmeiner, P. Conjugated enynes as nonaromatic catechol bioisosteres: synthesis, binding experiments, and computational studies of novel dopamine receptor agonists recognizing preferentially the D3 subtype. J. Med. Chem. 2000, 43, 756-762.
7. (b) Lenz, C.; Haubmann, C.; Huebner, H.; Boeckler, F.; Gmeiner, P. Fancy bioisosteres: synthesis and dopaminergic properties of the endiyne FAUC 88 as a novel non-aromatic D3 agonist. Bioorg. Med. Chem. 2004, 13, 185-191.
8. (a) Ortner, B.; Waibel, R.; Gmeiner, P. Indoloparacyclophanes: synthesis and dopamine receptor binding of a novel arylbioisostere. Angew. Chem., Int. Ed. 2001, 40, 1283-1285.
9. (b) Ortner, B.; Hübner, H.; Gmeiner, P. Planar chiral indoles: synthesis and biological effects of the enantiomers. Tetrahedron: Asymmetry 2001, 12, 3205-3208.
10. (a) Pilla, M.; Perachon, S.; Sautel, F.; Garrido, F.; Mann, A.; Wermuth, C. G.; Schwartz, J.-C.; Everitt, B. J.; Sokoloff, P. Selective inhibition of cocaine-seeking behaviour by a partial dopamine D3 receptor agonist. Nature 1999, 400, 371-375.
11. (b) Bezard, E.; Ferry, S.; Mach, U.; Stark, H.; Leriche, L.; Boraud, T.; Gross, C.; Sokoloff, P. Attenuation of levodopa-induced dyskinesia by normalizing dopamine D3 receptor function. Nat. Med. 2003, 9, 762-767.
12. (a) van Staveren, D. R.; Metzler-Nolte, N. Bioorganometallic chemistry of ferrocene. Chem. Rev. 2004, 104, 5931-5985.
13. (b) Wenzel, M.; Wu, Y. Ferrocene, ruthenocene and rhodocene analogs in haloperidol synthesis and organ distribution after labeling with 103Ru and 103mRh. Int. J. Radiat. Appl. Instrum., Part A 1988, 39, 1237-1241.
14. (a) Rausch, M. D.; Fischer, E. O.; Grubert, H. The aromatic reactivity of ferrocene, ruthenocene, and osmocene. J. Am. Chem. Soc. 1960, 82, 76-82.
15. (b) Reeves, P. C. Carboxylation of aromatic compounds: ferrocenecarboxylic acid. Org. Synth. 1977, 56, 28-31.
16. (a) Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. Simple, efficient catalyst system for the palladium-catalyzed amination of aryl chlorides, bromides, and triflates. J. Org. Chem. 2000, 65, 1158-1174.
17. (b) Hartwig, J. F. Transition metal catalyzed synthesis of arylamines and aryl ethers from aryl halides and triflates: scope and mechanism. Angew. Chem., Int. Ed. 1998, 37, 2046-2067.
18. (a) Nishiyama, M.; Yamamoto, T.; Koie, Y. Synthesis of N-arylpiperazines from aryl halides and piperazine under a palladium tri-tert-butylphosphine catalyst. Tetrahedron Lett. 1998, 39, 617-620.
19. (b) Torisawa, Y.; Nishi, T.; Minamikawa, J.-i. Progress in arylpiperazine synthesis by the catalytic amination reaction. Bioorg. Med. Chem. 2002, 10, 4023-4027.
20. Plazuk, D.; Zakrzewski, J. Friedel-Crafts Type reaction of ferrocene with β-ketoesters. J. Org. Chem. 2002, 67, 8672-8674.
21. B subtypes in a heterologous cell line. Mol. Endocrinol. 1992, 6, 920-926.
22. Sokoloff, P.; Andrieux, M.; Besançon, R.; Pilon, C.; Martres, M.-P.; Giros, B.; Schwartz, J.-C. Pharmacology of human dopamine D3 receptor expressed in a mammalian cell line: comparison with D2 receptor. Eur. J. Pharmacol. 1992, 225, 331-337.
23. Asghari, V.; Sanyal, S.; Buchwaldt, S.; Paterson, A.; Jovanovic, V.; Van Tol, H. H. M. Modulation of intracellular cyclic AMP levels by different human dopamine D4 receptor variants. J. Neurochem. 1995, 65, 1157-1165.
24. (a) Mierau, J.; Schneider, F. J.; Ensinger, H. A.; Chio, C. L.; Lajiness, M. E.; Huff, R. M. Pramipexole binding and activation of cloned and expressed dopamine D2, D3 and D4 receptors. Eur. J. Pharmacol. 1995, 290, 29-36.
25. (b) Hübner, H.; Kraxner, J.; Gmeiner, P. Cyanoindole derivatives as highly selective dopamine D4 receptor partial agonists: solid-phase synthesis, binding assays, and functional experiments. J. Med. Chem. 2000, 43, 4563-4569.
26. Chio, C.; Lajiness, M. E.; Huff, R. M. Activation of heterologously expressed D3 dopamine receptors: comparison with D2 dopamine receptors. Mol. Pharmacol. 1994, 45, 51-60.
27. long dopamine receptors expressed in recombinant cells. Br. J. Pharmacol. 1996, 118, 1544-1550.
28. 35S] Guanosine-5′-0-(3-thio)triphosphate binding as a measure of efficacy at human recombinant dopamine D4.4 receptors: actions of antiparkinsonian and antipsychotic agents. J. Pharmacol. Exp. Ther. 1997, 282, 181-191.
29. Meyer, E. A.; Castellano, R. K.; Diederich, F. Interactions with aromatic rings in chemical and biological recognition. Angew. Chem., Int. Ed. 2003, 42, 1210-1250.
30. Allen, F. H. The Cambridge Structural Database: a quarter of a million crystal structures and rising. Acta Crystallogr. 2002, B58, 380-388.
31. PC Spartan Plus; Wavefunction Inc.: Irvine, CA, 1998.
32. SYBYL 6.9.1, Tripos Inc. (1699 South Hanley Rd, St. Louis, MO, 63144).