Substituted naphthofurans as hallucinogenic phenethylamine -Ergoline hybrid molecules with unexpected muscarinic antagonist activity

Journal of Medicinal Chemistry

Volumn 41, Issue 12, 1998, Pages 2134-2145

  Monte, Aaron P ^d   Marona Lewicka, Danuta ^e   Lewis, Mechelle M ^b   Mailman, Richard B ^b   Wainscott, David B ^c   Nelson, David L ^c   Nichols, David E ^a  

^a PURDUE UNIVERSITY   (United States)

^b UNIVERSITY OF NORTH CAROLINA SCHOOL OF MEDICINE   (United States)

^c ELI LILLY AND COMPANY   (United States)

^d UNIVERSITY OF WISCONSIN LA CROSSE   (United States)

^e NONE

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINO 8 BROMO 6 METHOXY 2A,3,4,5 TETRAHYDRO 2H NAPHTHO[1,8 BC]FURAN; ERGOLINE DERIVATIVE; FURAN DERIVATIVE; MUSCARINIC RECEPTOR BLOCKING AGENT; NAPHTHOFURAN DERIVATIVE; PHENETHYLAMINE DERIVATIVE; PSYCHEDELIC AGENT; SEROTONIN 2A RECEPTOR; SEROTONIN 2C RECEPTOR; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; HALLUCINATION; NONHUMAN; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION;

ANIMALS; BINDING, COMPETITIVE; BRAIN; CELL LINE; CRICETINAE; DISCRIMINATION LEARNING; ERGOLINES; FURANS; HALLUCINOGENS; HUMANS; LYSERGIC ACID DIETHYLAMIDE; MALE; MICE; MUSCARINIC ANTAGONISTS; PHENETHYLAMINES; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, MUSCARINIC; RECEPTORS, SEROTONIN; RECOMBINANT PROTEINS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TETRAHYDRONAPHTHALENES;

EID: 0032482317     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980076u     Document Type: Article

References (45)

1. 2 Receptor. Mol. Pharmacol. 1990, 38 604-609.
2. Pierce, P. A.; Peroutka, S. J. Hallucinogenic Drug Interactions with Neurotransmitter Receptor Binding Sites in Human Cortex. Psychopharmacology 1989, 97, 118-122.
3. 2 Receptor Subtypes. Mol. Pharmacol. 1990, 38, 594-598.
4. Marini-Bettolo, G. B.; Chiavarelli, S.; Bovet, D. Synthetic Sympatholytic Substances of the Ergotamine Series. I. Nitrogen-Substituted Derivatives of the dl-1,2,3,4-Tetrahydro-2-Naphthylamine-Containing Amino and Amido Functional Groups. Gazz. Chim. Ital. 1951, 80, 281-298.
5. 2 Receptor: Identification of Amino Acids Necessary for Ligand Binding and Receptor Activation. Mol. Pharmacol. 1993, 43, 931-940.
6. 2 receptor from a human to a rat pharmacology. FEBS Lett. 1992, 307, 324-328.
7. Nichols, D. E.; Barfknecht, C. F.; Rusterholz, D. B.; Benington, F.; Morin, R. D. Asymmetric Synthesis of Psychotomimetic Phenylisopropylamines. J. Med. Chem. 1973, 16, 480-483.
8. Shulgin, A. T.; Dyer, D. C. Psychotomimetic Phenylisopropylamines. 5. 4-Alkyl-2,5-Dimethoxyphenylisopropylamines. J. Med. Chem. 1975, 18, 1201-1204.
9. Glennon, R. A.; Young, R.; Jacyno, J. M. Indolalkylamine and Phenalkylamine Hallucinogens. Biochem. Pharmacol. 1983, 32, 1267-1273.
10. Monte, A. P.; Marona-Lewicka, D.; Parker, M. A.; Mayleben, M.; Mailman, R. B.; Wainscott, B.; Nelson, D. L.; Nichols, D. E. Dihydrobenzofuran Analogues of Hallucinogens. 3. Models of 4-Substituted (2,5-Dimethoxyphenyl)alkylamine Derivatives with Rigidified Methoxy Groups. J. Med. Chem. 1996, 39, 2953-2961.
11. Appel, J. B.; Cunningham, K. A. The Use of Drug Discrimination Procedures to Characterize Hallucinogenic Drug Actions. Psychopharmacol. Bull. 1986, 22, 959-967.
12. Jung, M. E.; Abrecht, S. Improved Synthesis of 3-Substituted 7-Methoxybenzofurans, Useful Intermediates for Preparation of Morphine Analogues. J. Org. Chem. 1988, 53, 423-425.
13. Chan, J. H.-T.; Elix, J. A.; Ferguson, B. A. Annelated Furans. XVII The Wittig Reaction of Benzofurans. Aust. J. Chem. 1975, 28, 1097-1111.
14. McKervey, M. A.; Tuladhar, S. M.; Twohig, M. F. Efficient Synthesis of Bicyclo[5.3.0]decatrienones and of 2-Tetralones via Rhodium(II) Acetate-Catalysed Cyclization of α-Diazoketones Derived from 3-Arylpropionic Acids. J. Chem. Soc., Chem. Commun. 1984, 129-130.
15. Beames, D. J.; Mander, L. N. Studies on Intramolecular Alkylation. IV. The Preparation of Spirodienones from Phenolic Diazoketones. Aust. J. Chem. 1974, 27, 1257-1268.
16. Cushman, M.; Choong, T.-C.; Valko, J. T.; Koleck, M. P. Total Synthesis of (±)-Chelidonine. J. Org. Chem. 1980, 45, 5067-5073.
17. Cushman, M.; Abbaspour, A.; Gupta, Y. P. Total Synthesis of (±)-14-Epicorynoline, (±)-Corynoline, and (±)-6-Oxocorynoline. J. Am. Chem. Soc. 1983, 105, 2873-2879.
18. Borch, R. F.; Hassid, A. I. A New Method for the Methylation of Amines. J. Org. Chem. 1972, 37, 1673-1674.
19. 2 Receptor. Eur. J. Pharmacol. 1993, 239, 111-118.
20. 2 Antagonists: Novel Structures and Pharmacology. Life Sci. 1993, 52, 497-503.
21. Freedman, S. B.; Dawson, G. R.; Iversen, L. L.; Baker, R.; Hargreaves, R. J. The Design of Novel Muscarinic Partial Agonists that Have Functional Selectivity in Pharmacological Preparations in Vitro and Reduced Side-Effect Profile in Vivo. Life Sci. 1993, 52, 489-495.
22. Lambrecht, G.; Moser, U.; Grimm, U.; Pfaff, O.; Hermanni, U.; Hildebrandt, C.; Waelbroeck, M.; Christophe, J.; Mutschler, E. New Functionally Selective Muscarinic Agonists. Life Sci. 1993, 52, 481-488.
23. Wess, J. Molecular Basis of Muscarinic Acetylcholine Receptor Function. TiPS 1993, 14, 308-312.
24. 2 Subtype. Life Sci. 1993, 53, 1743-1751.
25. Tomaszewski, Z.; Johnson, M. P.; Huang, X.; Nichols, D. E. Benzofuran Isosteres of Hallucinogenic Tryptamines. J. Med. Chem. 1992, 35, 2061-2064.
26. De Boer, T. J.; Backer, H. J. Diazomethane. Organic Syntheses; Wiley: New York, 1963; Collect. Vol. IV, pp 250-253.
27. Black, T. H. The Preparation and Reactions of Diazomethane. Aldrichim. Acta 1983, 16, 3-10.
28. Boegesoe, K. P.; Perregaard, J. K. 3-Aminomethyl Derivatives of Indane, Indoline, and Dihydrobenzofuran and Thiophene. European Patent Application No. 0 281 261 A2; July 9, 1988.
29. Nichols, D. E.; Snyder, S. E.; Oberlender, R.; Johnson, M. P.; Huang, X. 2,3-Dihydrobenzofuran Analogues of Hallucinogenic Phenethylamines. J. Med. Chem. 1991, 34, 276-281.
30. Oberlender, R.; Nichols, D. E. (+)-N-Methyl-1-(1,3-benzodioxol5-yl)-2-butanamine as a Discriminitive Stimulus in Studies of 3,4-Methylenedioxyamphetamine-Like Behavioral Activity. J. Pharmacol. Exp. Ther. 1990, 255, 1098-1106.
31. Oberlender, R.; Nichols, D. E. Drug Discrimination Studies with MDMA and Amphetamine. Psychopharmacology 1988, 95, 71-76.
32. Litchfield, J. T.; Wilcoxon, F. A. A Simplified Method of Evaluating Dose-Effect Experiments. J. Pharmacol. Exp. Ther. 1949, 96, 99-113.
33. 2 Receptor in Rat Frontal Cortex. Pharmacol. Biochem. Behav. 1990, 35, 211-217.
34. 2F Receptor. Mol. Pharmacol. 1993, 43, 419-426.
35. Bradford, M. M. A. A Rapid and Sensitive Method for the Quantitation of Microgram Quantities of Protein Utilizing the Principle of Protein-Dye Binding. Anal. Biochem. 1976, 72, 248-254.
36. 2 Receptor: Structurally Specific Differentiation by Ergolines and Tryptamines. J. Pharmacol. Exp. Ther. 1993, 265, 1272-1279.
37. 2β) Receptor. Naunyn-Schmiedebergs Arch. Pharmacol. 1998, 357, 17-24.
38. Pazos, A.; Hoyer, D.; Palacios, J. M. Mesulergine, a Selective Serotonin-2 Ligand in the Rat Cortex: Evidence for Species Differences in Brain Serotonin-2 Receptors. Eur. J. Pharmacol. 1985, 106, 531-538.
39. 1 Muscarinic Receptor is Associated with the Hydrolysis of Phosphatidylinositols in Transfected B82 Cells. Life Sci. 1988, 42, 2489-2502.
40. Lai, J.; Bloom, J. W.; Yamamura, H. I.; Roeske, W. R. Amplification of the rat M2 muscarinic receptor gene by the polymerase chain reaction: functional expression of the M2 muscarinic receptor. Life Sci. 1990, 47, 1001-1013.
41. Kashihara, K; Varga, E. V.; Waite, S. L.; Roeske, W. R.; Yamamura, H. I. Cloning of the rat M3, M4 and M5 muscarinic acetylcholine receptor genes by the polymerase chain reaction (PCR) and the pharmacological characterization of the expressed genes. Life Sci. 1992, 51, 955-971.
42. 1 Muscarinic Receptor and the Hydrolysis of Inositol Lipids in Transfected Murine Fibroblast Cells (B82) Expressing Different Receptor Densities. J. Pharmacol. Exp. Ther. 1989, 251, 90-97.
43. Harper, J. F.; Brooker, G. Femtomole Sensitive Radioimmunoassay for Cyclic AMP and Cyclic GMP after 2′O-Acetylation by Acetic Anhydride in Aqueous Solution. J. Cyclic Nucleotide Res. 1975, 1, 207-218.
44. 125I-Labeled Succinyl Cyclic Nucleotide Tyrosine Methyl Esters by High Performance Liquid Chromatography. Anal. Biochem. 1988, 168, 417-420.
45. 50) of an Enzymatic Reaction. Biochem. Pharmacol 1973, 22, 3099-3108.