Dopamine/serotonin receptor ligands. 16.1 Expanding dibenz[d,g]azecines to 11- and 12-membered homologues. Interaction with dopamine D1-D5 receptors

Journal of Medicinal Chemistry

Volumn 50, Issue 18, 2007, Pages 4528-4533

  Enzensperger, Christoph ^a   Müller, Franziska K U ^a   Schmalwasser, Bärbel ^a   Wiecha, Petra ^a   Traber, Heidi ^a   Lehmann, Jochen ^a  

^a FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2,3,4,5 TETRAHYDRO 7,8 DIHYDROXY 1 PHENYL 1H 3 BENZAZEPINE; 7 METHYL 5,6,7,8,9,14 HEXAHYDRODIBENZ[D,G]AZECINE; AZACYCLODODECENE; AZACYCLOUNDECENE; CLOZAPINE; DOPAMINE; DOPAMINE 1 RECEPTOR; DOPAMINE 2 RECEPTOR; DOPAMINE 3 RECEPTOR; DOPAMINE 4 RECEPTOR; DOPAMINE 5 RECEPTOR; DOPAMINE RECEPTOR; DOPAMINE RECEPTOR BLOCKING AGENT; ECOPIPAM; SEROTONIN RECEPTOR; UNCLASSIFIED DRUG;

ARTICLE; BISCHLER NAPIERALSKI CYCLIZATION; CELL STRAIN HEK293; CHLORINATION; CONTROLLED STUDY; CYCLIZATION; DEMETHYLATION; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HYDROLYSIS; LIGAND BINDING; RECEPTOR AFFINITY; RING OPENING; STRUCTURE ACTIVITY RELATION;

BINDING, COMPETITIVE; CELL LINE; HETEROCYCLIC COMPOUNDS, 3-RING; HUMANS; LIGANDS; MACROCYCLIC COMPOUNDS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RADIOLIGAND ASSAY; RECEPTORS, DOPAMINE; RECEPTORS, DOPAMINE D1; RECEPTORS, DOPAMINE D2; RECEPTORS, DOPAMINE D3; RECEPTORS, DOPAMINE D4; RECEPTORS, DOPAMINE D5;

EID: 34548489854     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm070388+     Document Type: Article

References (21)

1. Enzensperger, C.; Kilian, S.; Ackermann, M.; Koch, A.; Kelch, K.; Lehmann, J. Dopamine/serotonin receptor ligands. Part 15: Oxygenation of the benz-indolo-azecine LE 300 leads to novel subnanomolar dopamine D(1)/D(5) antagonists. Bioorg. Med. Chem. Lett 2007, 17, 1399-1402.
2. Pei, L.; Lee, F. J.; Moszczynska, A.; Vukusic, B.; Liu, F. Regulation of dopamine D1 receptor function by physical interaction with the NMDA receptors. J. Neurosci. 2004, 24, 1149-1158.
3. Liu, F.; Wan, Q.; Pristupa, Z. B.; Yu, X. M.; Wang, Y. T.; Niznik, H. B. Direct protein-protein coupling enables cross-talk between dopamine D5 and gamma-aminobutyric acid A receptors. Nature 2000, 403, 274-280.
4. Burnett, D. A. Preparation of benzazepines and benzonaphthazepines as selective dopamine D1/D5 receptor antagonists for the treatment of metabolic and CNS disorders. Schering Corporation. 2004-850530-[2005075325], 170. 2004. U.S. 20-5-2004.
5. Wu, W. L.; Burnett, D. A. Preparation of benzazepine derivatives as selective D1/D5 receptor antagonists for the treatment of obesity and CNS disorders. Schering Corporation. 2003-US26878[2004020442], 54. 2004. WO. 27-8-2003.
6. Price, K. L.; Middaugh, L. D. The dopamine D1 antagonist reduces ethanol reward for C57BL/6 mice. Alcohol: Clin. Exp. Res. 2004, 28, 1666-1675.
7. Romach, M. K.; Glue, P.; Kampman, K.; Kaplan, H. L.; Somer, G. R.; Poole, S.; Clarke, L.; Coffin, V.; Cornish, J.; O'Brien, C. P.; Sellers, E. M. Attenuation of the euphoric effects of cocaine by the dopamine D1/D5 antagonist ecopipam (SCH 39166). Arch. Gen. Psychiatry 1999, 56, 1101-1106.
8. Decker, M.; Lehmann, J. LE300. New results on its ability to antagonize the discriminative stimulus effects of cocaine. Dopamine/serotonin receptor antagonists, part XI. Pharmazie 2006, 61, 248-250.
9. Elliot, E. E.; Sibley, D. R.; Katz, J. L. Locomotor and discriminative-stimulus effects of cocaine in dopamine D5 receptor knockout mice. Psychopharmacology (Berlin) 2003, 169, 161-168.
10. Horacek, J.; Bubenikova-Valesova, V.; Kopecek, M.; Palenicek, T.; Dockery, C.; Mohr, P.; Hoschl, C. Mechanism of action of atypical antipsychotic drugs and the neurobiology of schizophrenia. CNS Drugs 2006, 20, 389-409.
11. Meltzer, H. Y. What's atypical about atypical antipsychotic drugs? Curr. Opin. Pharmacol. 2004, 4, 53-57.
12. Hoefgen, B.; Decker, M.; Mohr, P.; Schramm, A. M.; Rostom, S. A.; El Subbagh, H.; Schweikert, P. M.; Rudolf, D. R.; Kassack, M. U.; Lehmann, J. Dopamine/serotonin receptor ligands. 10: SAR studies on azecine-type dopamine receptor ligands by functional screening at human cloned D1, D2L, and D5 receptors with a microplate reader based calcium assay lead to a novel potent D1/D5 selective antagonist. J. Med. Chem. 2006, 49, 760-769.
13. Wittig, T. W.; Enzensperger, C.; Lehmann, J. Dopamine/serotonin receptor ligands VI. Dibenz[g,j]-1-oxa-4-azacycloundecene and dibenz[d,g]- 2-azacycloundecene: synthesis of two new heterocyclic ring systems as potential ligands for dopamine receptor subtypes. Heterocycles 2003, 60, 887-898.
14. Enzensperger, C.; Lehmann, J. Dopamine/serotonin receptor ligands. 13: Homologization of a benzindoloazecine-type dopamine receptor antagonist modulates the affinities for dopamine D(1)-D(5) receptors. J. Med. Chem. 2006, 49, 6408-6411.
15. Tanaka, T.; Hayasaka, T.; Saito, K.; Narita, S. Synthesis of 5,6,7,8,9,-14-hexahydrodibenz[d,g]azecine derivatives. J. Pharm. Soc. Jpn. 1977, 98 (5), 649-652.
16. Schlueter, G.; Meise, W. Isoquino[1,2-a][2]benzazepines. II. Preparation of 1-phenyl[2]benzazepines derivatives by Bischler-Napieralski reaction. Liebigs Ann. Chem. 1988, 9, 833-837.
17. Meise, W.; Onusseit, O.; Clemens, M. Synthesis of isoquino[1,2-alpha][2] benzazepines and biochemical testing of isomeric homoberbines and related papaverine-derivatives on the inhibition of phosphodiesterases. Pharmazie 1999, 54, 658-666.
18. Krollpfeiffer, F.; Mueller, A. Phenacylpyridinium compounds. Chem. Ber. 1935, 68B, 1169-1177.
19. Calverley, M. J. Chloroformate ester-induced reductive 1,2-bond cleavage of 1,2,3,4-tetrahydro-beta-carboline derivatives. Stereochemistry and application in sequence with an oxidative bond regeneration reaction to the synthesis of indole alkaloids. J. Chem. Res., Synop. 1983, 1848-1890.
20. Mohr, P.; Decker, M.; Enzensperger, C.; Lehmann, J. Dopamine/serotonin receptor ligands. 12(1): SAR studies on hexahydro-dibenz-[d,g]azecines lead to 4-chloro-7-methyl-5,6,7,8,9,14-hexahydrodibenz-[d,g]azecin-3-ol, the first picomolar D5-selective dopamine-receptor antagonist. J. Med. Chem. 2006, 49, 2110-2116.
21. NIMH. Psychoactive Drug Screening Program (PDSP), 2006. http://pdsp.med.unc.edu/pdsp.php.