Synthesis of tropeines and allosteric modulation of ionotropic glycine receptors

Journal of Medicinal Chemistry

Volumn 47, Issue 25, 2004, Pages 6384-6391

  Maksay, Gabor ^a   Nemes, Péter ^b   Biró, Tímea ^a  

^a CHEMICAL RESEARCH CENTER   (Hungary)

^b SZENT ISTVÁN UNIVERSITY   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

3ALPHA (2',3' BENZOFURAN 5',5' DIMETHYL 8' CHLORO 6' CARBONYLOXO)NORTROPANE; 3ALPHA AMINOTROPANE DERIVATIVE; 3ALPHA BENZOYLAMIDOTROPANE; 3ALPHA BENZOYLOXYNORTROPANE; 3ALPHA HYDROXYNORTROPANE DERIVATIVE; 3BETA BENZOYLOXYNORTROPANE; 3BETA HYDROXYNORTROPANE DERIVATIVE; AMIDE; BENZOIC ACID DERIVATIVE; ESTER DERIVATIVE; GLYCINE; GLYCINE RECEPTOR; GRANISETRON; IONOTROPIC RECEPTOR; RECEPTOR SUBUNIT; SEROTONIN 3 ANTAGONIST; SEROTONIN 3 RECEPTOR; STRYCHNINE; TRITIUM; TROPANE DERIVATIVE; TROPEINE DERIVATIVE; UNCLASSIFIED DRUG;

ALLOSTERISM; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; BINDING ASSAY; BRAIN CORTEX; CARBON NUCLEAR MAGNETIC RESONANCE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DEMETHYLATION; DISSOCIATION CONSTANT; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; HYDROGEN BOND; HYDROPHOBICITY; MALE; MOLECULAR INTERACTION; MOLECULAR MODEL; NONHUMAN; PHARMACOPHORE; PROTON NUCLEAR MAGNETIC RESONANCE; RAT; RECEPTOR AFFINITY; RECEPTOR OCCUPANCY; REGULATORY MECHANISM; SPINAL CORD; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNAPTIC MEMBRANE;

ALLOSTERIC REGULATION; AMIDES; ANIMALS; BENZOIC ACIDS; BINDING, COMPETITIVE; GLYCINE; MALE; MODELS, MOLECULAR; RATS; RATS, WISTAR; RECEPTORS, GLYCINE; RECEPTORS, SEROTONIN, 5-HT3; SPINAL CORD; STRUCTURE-ACTIVITY RELATIONSHIP; STRYCHNINE; TROPANES;

EID: 9744261667     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm040814g     Document Type: Article

References (29)

1. Aprison, M. H. The discovery of the neurotransmitter role of glycine. In: Glycine Neurotransmission; Ottersen, O. P., Storm-Mathisen, J., Eds.; John Wiley and Sons Ltd.: New York, 1990; pp 1-23.
2. Laube, B.; Maksay, G.; Schemm, R.; Betz, H. Modulation of glycine receptor activity: a novel approach for the therapeutic intervention at inhibitory synapses? Trends Pharmacol. Sci. 2002, 23, 519-527.
3. Breitinger, H. G.; Becker, C. M. The inhibitory glycine receptor: Prospects for a therapeutic orphan? Curr. Pharm. Des. 1998, 4, 315-334.
4. Laube, B.; Kuhse, J.; Rundström, N.; Kirsch, J.; Schmieden, V.; Betz, H. Modulation by zinc ions of native rat and recombinant human inhibitory glycine receptors. J. Physiol. 1995, 483, 613-619.
5. Mascia, M. P.; Machu, T. K.; Harris, R. A. Enhancement of homomeric glycine receptor function by long-chain alcohols and anaesthetics. Br. J. Pharmacol. 1996, 119, 1331-1336.
6. 3 antagonists in rat spinal cord. Br. J. Pharmacol. 1996, 118, 2115-2125.
7. Maksay, G.; Laube, B.; Betz, H. Selective blocking effects of tropisetron and atropine on recombinant glycine receptors. J. Neurochem. 1999, 73, 802-806.
8. Supplisson, S.; Chesnoy-Marchais, D. Glycine receptor β subunits play a critical role in potentiation of glycine responses by ICS-205,930. Mol. Pharmacol. 2000, 58, 763-770.
9. Maksay, G.; Laube, B.; Betz, H. Subunit-specific modulation of glycine receptors by neurosteroids. Neuropharmacology 2001, 41, 369-376.
10. 3 serotonin receptor ligands. Neuropharmacology 1998, 37, 1633-1641.
11. 3 receptor antagonists: insight into selectivity. Eur. J. Pharmacol. 2000, 402, 205-213.
12. Maksay, G.; Bíró, T. Dual cooperative allosteric modulation of binding to ionotropic glycine receptors. Neuropharmacology 2002, 43, 1087-1098 (Erratum: Neuropharmacology 2003, 44, 843).
13. Maksay, G.; Bíró, T. Dual cooperative allosteric modulation of binding to ionotropic glycine receptors. Neuropharmacology 2002, 43, 1087-1098 (Erratum: Neuropharmacology 2003, 44, 843).
14. 3 receptor antagonists: synthesis and pharmacological activity of various aromatic esters and amides derived from tropane and 1,2,6-trisubstituted piperidine. Eur. J. Med. Chem. 1993, 28, 869-880.
15. Wallace, J. L.; Kidd, M. R.; Cauthen, S. E.; Woodyard, J. D. The synthesis of several para-substituted tropanyl benzoates. J. Heterocycl. Chem. 1978, 15, 315-317.
16. Kraiss, G.; Nádor, K. A convenient synthesis of nortropine from tropine or tropinone. Tetrahedron Lett. 1971, 1, 57-58.
17. Wallace, J. L.; Kidd, M. R.; Cauthen, S. E.; Woodyard, J. D. New compounds: synthesis of para-substituted nortropanyl benzoates. J. Pharm. Sci 1980, 69, 1357-1358.
18. Momose, T.; Toshima, M.; Toyooka, N.; Hirai, Y.; Eugster, C. H. Bicyclo[3.3.1]nonanes as synthetic intermediates. Part 19. Asymmetric cleavage of ω-azabicyclo[3.n.1]alkan-3-ones at the 'fork head'. J. Chem. Soc., Perkin Trans. 1 1997, 1307-1314.
19. Lindenmann, A. Alkaloid synthesis. X. Syntheses of 6-alkoxy-tropane derivatives. Helv. Chim. Acta 1959, 42, 490-495.
20. Allegretti, M.; Berdini, V.; Cesta, M. C.; Curti, R.; Nicolini, L.; Topai, A. One-pot, new stereoselective synthesis of endo-tropanamine. Tetrahedron Lett. 2001, 42, 4257-4259.
21. 3 receptor antagonist: synthesis and structure-activity relationships. J. Med. Chem. 1992, 35, 310-319.
22. 3 and nACh ionotropic receptors: A perspective from the computational chemistry point of view. Curr. Med. Chem. 2002, 9, 99-125.
23. Agar, J. T. H.; Evans, W. C. Alkaloids of the genus Erythroxylum. Part 1. E. monogynumRoxb. roots. J. Chem. Soc., Perkin Trans, 1 1976, 1550-1558.
24. Nádor, K.; Scheiber, P. Konformationsanalyse der Tropeine: Konformation des Benzoyltropins und Benzoyl-ψ-tropins (Tropakokain) und ihre cholinolytische Wirkung. Arzneimittel forschung (Drug Res.) 1972, 22, 459-462.
25. Singh, S. P.; Kaufman, D.; Stenberg, V. I. J. Nitrogen photochemistry. Cocaine and its model compounds. J. Heterocycl. Chem. 1979, 16, 625-631.
26. Egyesult Gyogyszer es Tapszergyar. Patent BE 622,090, 1961. Tropeine derivatives. Chem. Abstr. 1964, 60, 576b.
27. Swain, C. J.; Baker, R.; Kneen, C.; Herbert, R.; Moseley, J.; Saunders, J.; Seward, E. M.; Stevenson, G. I.; Beer, M.; Stanton, J.; Watling, K; Ball, R. G. Novel 5-HT3 antagonists: indol-3-ylspiro(azabicycloalkane-3, 5′(4′H)-oxazoles). J. Med. Chem. 1992, 35, 1019-1031.
28. Hideo, I.; Yohya, W.; Chihiro, K. A new synthetic route to tropane alkaloids based on [4+2] nitroso cycloaddition to 1,3-cycloheptadienes. J. Org. Chem. 1985, 50, 1818-1825.
29. 3H]granisetron binding. J. Neurochem. 1996, 67, 407-412.