Synthesis and pharmacological characterization of a series of geometrically constrained 5-HT2A/2C receptor ligands

Journal of Medicinal Chemistry

Volumn 46, Issue 16, 2003, Pages 3526-3535

  Chambers, James J ^a   Parrish, Jason C ^a   Jensen, Niels H ^a   Kurrasch Orbaugh, Deborah M ^a   Marona Lewicka, Danuta ^a   Nichols, David E ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

(6 METHOXY 2A,3,4,5 TETRAHYDRO 2H NAPHTHO[1,8 BC]FURAN 5 YL)AMINOMETHANE; (6 METHOXY 4,5 DIHYDRO 3H NAPHTHO[1,8 BC]FURAN 5 YL)AMINOMETHANE HEMIOXALATE; (8 BROMO 6 METHOXY 2A,3,4,5 TETRAHYDRO 2H NAPHTHO[1,8 BC]FURAN 5 YL)AMINOMETHANE; (8 BROMO 6 METHOXY 4,5 DIHYDRO 3H NAPHTHO[1,8 BC]FURAN 5 YL)AMINOMETHANE; FURAN DERIVATIVE; IOFETAMINE I 125; LYSERGIDE; PHOSPHATIDYLINOSITIDE; SEROTONIN 1A RECEPTOR; SEROTONIN 2A AGONIST; SEROTONIN 2A RECEPTOR; SEROTONIN 2C AGONIST; SEROTONIN 2C RECEPTOR; SODIUM CHLORIDE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; BINDING KINETICS; CONTROLLED STUDY; DRUG ACTIVITY; DRUG CONFORMATION; DRUG DETERMINATION; DRUG DISCRIMINATION; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG SYNTHESIS; HYDROLYSIS; IN VITRO STUDY; MALE; NONHUMAN; RAT; RECEPTOR AFFINITY; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

ANIMALS; BINDING, COMPETITIVE; CELLS, CULTURED; DISCRIMINATION LEARNING; FURANS; HETEROCYCLIC COMPOUNDS, 3-RING; INOSITOL PHOSPHATES; LIGANDS; LYSERGIC ACID DIETHYLAMIDE; MALE; MOLECULAR CONFORMATION; RADIOLIGAND ASSAY; RATS; RATS, SPRAGUE-DAWLEY; RECEPTOR, SEROTONIN, 5-HT2A; RECEPTOR, SEROTONIN, 5-HT2C; RECEPTORS, SEROTONIN; RECEPTORS, SEROTONIN, 5-HT1; SEROTONIN AGONISTS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0041342057     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm030064v     Document Type: Article

References (28)

1. Monte, A. P.; Marona-Lewicka, D.; Cozzi, N. V.; Nichols, D. E. Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4-(methylenedioxy)amphetamine. J. Med. Chem. 1993, 36, 3700-3706.
2. 2A receptor. J. Med. Chem. 1998, 41, 5148-5149.
3. (2A/2C) receptor agonists. J. Med. Chem. 2001, 44, 1003-1010.
4. Monte, A. P.; Marona-Lewicka, D.; Lewis, M. M.; Mailman, R. B.; Wainscott, D. B.; Nelson, D. L.; Nichols, D. E. Substituted naphthofurans as hallucinogenic phenethylamine-ergoline hybrid molecules with unexpected muscarinic antagonist activity. J. Med. Chem. 1998, 41, 2134-2145.
5. Makriyannis, A.; Knittel, J. Conformational-analysis of amphetamine in solution based on unambiguous assignment of the diastereotopic benzylic protons in the H-1-NMR spectra. Tetrahedron Lett. 1981, 22, 4631-4634.
6. Spartan 5.0; Wavefunction, Inc., 18401 Von Karman Ave, Ste 370, Irvine, California, 92612.
7. Curran, D. P.; Xu, J. o-Bromo-p-methoxyphenyl ethers. Protecting/radical translocating (PRT) groups that generate radicals from C-H bonds β to oxygen atoms. J. Am. Chem. Soc. 1996, 118, 3142-3147.
8. Sunitha, K.; Balasubramanian, K. K. A reinvestigation of the Claisen rearrangement of methyl gamma-aryloxycrotonates. A convenient synthesis of 3-ethylidenebenzofuran-2(3H)-ones. Tetrahedron 1987, 43, 3269-3278.
9. Shankaran, K.; Sloan, C. P.; Snieckus, V. Synthetic connections to the aromatic directed metalation reaction. Radical-induced cyclization to substituted benzofurans, benzopyrans, and furopyridines. Tetrahedron Lett. 1985, 26, 6001-6004.
10. Abraham, D. J.; Kennedy, P. E.; Mehanna, A. S.; Patwa, D. C.; Williams, F. L. Design, synthesis, and testing of potential antisickling agents. 4. Structure-activity relationships of benzyloxy and phenoxy acids. J. Med. Chem. 1984, 27, 967-978.
11. Barnett, C. J.; Wilson, T. M.; Wendel, S. R.; Winningham, M. J.; Deeter, J. B. Asymmetric synthesis of Lometrexol ((6R)-5,-10-dideaza-5,6,7,8-tetrahydrofolic acid). J. Org. Chem. 1994, 59, 7038-7045.
12. Horaguchi, S.; Mamoru, H.; Suzuki, T. Furan derivatives. IV. On the effects of substituents in the synthesis of 4,5-dihydro-3H-naphtho[1,8-bc]furans. Bull. Chem. Soc. Jpn. 1982, 55, 865-869.
13. Flaugh, M. E.; Mullen, D. L.; Fuller, R. W.; Mason, N. R. 6-Substituted 1,3,4,5-tetrahydrobenz[cd]indol-4-amines: potent serotonin agonists. J. Med. Chem. 1988, 31, 1746-1753.
14. Groutas, W. C.; Felker, D. Synthetic applications of cyanotrimethylsilane, iodotrimethylsilane, azidotrimethylsilane, and methylthiotrimethylsilane. Synthesis 1980, 11, 861-868.
15. DeBernardis, J. F.; Kyncl, J. J.; Basha, F. Z.; Arendsen, D. L.; Martin, Y. C.; Winn, M.; Kerkman, D. J. Conformationally defined adrenergic agents. 2. Catechol imidazoline derivatives: biological effects at α1 and α2 adrenergic receptors. J. Med. Chem. 1986, 29, 463-467.
16. Haefliger, W. V.; Klöppner, E. Stereospezifische synthese einer neuen morphin-teilstruktur (Stereospecific synthesis of a new morphine structure). Helv. Chim. Acta 1982, 65, 1837-1852.
17. Leanna, M. R.; Martinelli, M. J.; Varie, D. L.; Kress, T. J. Diasteroselectivity in ergoline synthesis: A face selective epoxidation. Tetrahedron Lett. 1989, 30, 3935-3938.
18. Thompson, H. W. Stereochemical control of reductions. The directive effect of carbomethoxy vs hydroxymethyl groups in catalytic hydrogenation. J. Org. Chem. 1971, 36, 2577-2581.
19. Thompson, H. W.; McPherson, E.; Lences, B. L. Stereochemical control of reductions. 5. Effects of electron density and solvent on group haptophilicity. J. Org. Chem. 1976, 41, 2903-2906.
20. Ranade, V. S.; Consiglio, G.; Prins, R. Functional-group-directed diastereoselective hydrogenation of aromatic compounds. 2(1). J. Org. Chem. 2000, 65, 1132-1138.
21. Shulgin, A. T.; Sargent, T.; Naranjo, C. Structure-activity relationships of one-ring psychotomimetics. Nature 1969, 221, 537-541.
22. 2A/2C agonist. J. Med. Chem. 1994, 37, 4346-4351.
23. Monte, A. P.; Marona-Lewicka, D.; Kanthasamy, A.; Sanders-Bush, E.; Nichols, D. E. Stereoselective LSD-like activity in a series of D-lysergic acid amides of (R)- and (S)-2-aminoalkanes. J. Med. Chem. 1995, 38, 958-966.
24. 2A receptor derived from an in silico activated G-protein coupled receptor. J. Comput.-Aided Mol. Des. 2002, 16, 511-520.
25. Monte, A. P.; Waldman, S. R.; Marona-Lewicka, D.; Wainscott, D. B.; Nelson, D. L.; Sanders-Bush, E.; Nichols, D. E. Dihydrobenzofuran analogues of hallucinogens. 4. Mescaline derivatives. J. Med. Chem. 1997, 40, 2997-3008.
26. 2 receptor defines a family of structurally distinct but functionally conserved serotonin receptors. Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 928-932.
27. Berg, K. A.; Clarke, W. P.; Sailstad, C.; Saltzman, A.; Maayani, S. Signal transduction differences between 5-hydroxytryptamine type 2A and type 2C receptor systems. Mol. Pharmacol. 1994, 46, 477-484.
28. Marona-Lewicka, D.; Kurrasch-Orbaugh, D. M.; Selken, J. R.; Cumbay, M. G.; Lisnicchia, J. G.; Nichols, D. E. Reevaluation of lisuride pharmacology: 5-hydroxytryptaminelA receptor-mediated behavioral effects overlap its other properties. Psychopharmacology 2002, 164, 93-107.