Homoazanicotine: A structure-affinity study for nicotinic acetylcholine (nACH) receptor binding

Journal of Medicinal Chemistry

Volumn 45, Issue 21, 2002, Pages 4724-4731

  Ferretti, G ^a,b   Dukat, M ^b   Giannella, M ^a   Piergentili, A ^a   Pigini, M ^a   Quaglia, W ^a   Damaj, M I ^b   Martin, B R ^b   Glennon, R A ^b  

^a UNIVERSITY OF CAMERINO   (Italy)

^b VIRGINIA COMMONWEALTH UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 [(1 METHYL) 4,5 DIHYDRO 1H IMIDAZOL 2 YL)METHYL]PYRIDINE; HOMOAZANICOTINE; IMIDAZOLINE; METHYL GROUP; NICOTINIC AGENT; NICOTINIC RECEPTOR; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; AROMATIZATION; ARTICLE; CONTROLLED STUDY; DEMETHYLATION; DRUG RECEPTOR BINDING; DRUG STRUCTURE; NONHUMAN; PHYSICAL CHEMISTRY; RAT; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION;

ACETAMIDES; ANIMALS; IMIDAZOLES; LIGANDS; MALE; MICE; MICE, INBRED ICR; NICOTINE; PAIN MEASUREMENT; PYRIDINES; RADIOLIGAND ASSAY; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, NICOTINIC; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0037057581     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm020188s     Document Type: Article

References (37)

1. Arneric, S. P.; Brioni, J. D., Eds. Neuronal Nicotinic Receptors; John Wiley and Sons: New York, 1999.
2. Lindstrom, J. Purification and cloning of nicotinic acetylcholine receptors. In Neuronal Nicotinic Receptors; Arneric, S. P., Brioni, J. D., Eds.; John Wiley and Sons: New York, 1999; pp 3-23.
3. Holladay, M. W.; Dart, M. J.; Lynch, J. K. Neuronal nicotinic acetylcholine receptors as targets for drug discovery. J. Med. Chem. 1997, 40, 4169-4194.
4. Decker, M. W.; Arneric, S. P. Nicotinic acetylcholine receptor-targeted compounds: A summary of the development pipeline and therapeutic potential. In Neuronal Nicotinic Receptors; Arneric, S. P., Brioni, J. D., Eds.; John Wiley and Sons: New York, 1999; pp 395-411.
5. Glennon, R. A.; Dukat, M. Nicotine receptor ligands. Med. Chem. Res. 1996, 6, 465-486.
6. Glennon, R. A.; Dukat, M. Nicotinic cholinergic receptor pharmacophores. In Neuronal Nicotinic Receptors; Arneric, S. P., Brioni, J. D., Eds.; John Wiley and Sons: New York, 1999; pp 271-284.
7. Glennon, R. A.; Dukat, M. Central nicotinic receptor ligands and pharmacophores. Pharm. Helv. Acta 2000, 74, 103-114.
8. Abreo, M. A.; Lin, N. H.; Garvey, D. S.; Gunn, D. E.; Hettinger, A. M.; Wasicak, J. T.; Pavlik, P. A.; Martin, Y. C.; Donnelly-Roberts, D. L.; Anderson, D. J.; Sullivan, J. P.; Williams, M.; Arneric, S. P.; Holladay, M. W. Novel 3-pyridyl ethers with subnanomolar affinity for central neuronal nicotinic acetylcholine receptors. J. Med. Chem. 1996, 39, 817-825.
9. Ferretti, G.; Dukat, M.; Giannella, M.; Piergentili, A.; Pigini, M.; Quaglia, W.; Damaj, M. I.; Martin, B. R.; Glennon, R. A. Chain-lengthened and imidazoline analogues of nicotine. Bioorg. Med. Chem. Lett. 2000, 10, 2665-2668.
10. Sakamoto, T.; Kondo, T.; Masumoto, K.; Yamanaka, H. Synthesis of methyl 2-(heteroaryl)propanoates via palladium-catalyzed reaction. Heterocycles 1993, 36, 2509-2512.
11. Agarwal, K. C.; Knaus, E. E. Synthesis and reactions of heterocyclic 2,3-epoxypropionitriles. J. Heterocycl. Chem. 1987, 24, 15-17.
12. Fromherz, K.; Spiegelberg, H. Pharmacologische Wirkung des β-Pyridylcarbinols (Niacol, Roche) und verwandter β-Pyridylvibinungen. Helv. Physiol. Pharmacol. Acta 1948, 6, 42-52.
13. Roth, B. L.; Kroeze, W. K.; Patel, S.; Lopez, E. The multiplicity of serotonin receptors: Uselessly diverse molecules or an embarrasment of riches? Neuroscientist 2000, 6, 252-262.
14. Cheng, Y.-X.; Dukat, M.; Dowd, M.; Fiedler, W.; Martin, B.; Damaj, M. I.; Glennon, R. A. Synthesis and binding of 6,7,8,9-tetrahydro-5H-pyrido[3,4-d]azepine and related ring-opened analogues at central nicotinic receptors. Eur. J. Med. Chem. 1999, 34, 177-190.
15. Glennon, R. A.; Maarouf, A.; Fahmy, S.; Martin, B.; Fan, F.; Yousif, Y.; Shafik, R. M.; Dukat, M. Structure-activity relationships of simple nicotine analogues. Med. Chem. Res. 1993, 2, 546-551.
16. Glassco, W.; May, E. L.; Damaj, M. I.; Martin, B. R. In vivo and in vitro activity of some N-substituted (±)nornicotine analogues. Med. Chem. Res. 1994, 4, 273-282.
17. Beers, W. H.; Reich, E. Structure and activity of acetylcholine. Nature 1970, 225, 917-922.
18. Sheridan, R. P.; Nilakantan, R.; Dixon, J. S.; Venkataraghavan, R. The ensemble approach to distance geometry: Application to the nicotinic pharmacophore. J. Med. Chem. 1986, 29, 899-906.
19. Caldwell, W. S.; Lippiello, P. M. Method for the treatment of neurodegenerative diseases. U.S. Patent 5,248,690, September 28, 1993.
20. Elliott, R. L.; Ryther, K. B.; Anderson, D. J.; Raszkiewicz, J. L.; Campbell, J. E.; Sullivan, J. P.; Garvey, D. S. Phenyl pyrrolidine analogues as potent nicotinic acetylcholine receptor (nAChR) ligands. Bioorg. Med. Chem. Lett. 1995, 5, 991-996.
21. Stitzel, J. A.; Jimenez, M.; Marks, M. J.; Tritto, T.; Collins, A. C. Potential role of the alpha4 and alpha6 nicotinic receptor subunits in regulating nicotine-induced seizures. J. Pharmacol. Exp. Ther. 2000, 293, 67-74.
22. Damaj, M. I.; Glassco, W.; Dukat, M.; Martin, B. R. Pharmacological characterization of nicotine-induced seizures in mice. J. Pharmacol. Exp. Ther. 1999, 291, 1284-1291.
23. McFarland, J. W.; Conover, L. H.; Howes, H. L.; Lynch, J. E.; Chisholm, D. R.; Austin, W. C.; Cornwell, R. L.; Danilewicz, J. C.; Courtney, W.; Morgan, D. H. Novel anthelmintic agents. II. Pyrantel and other cyclic amidines. J. Med. Chem. 1969, 12, 1066-1079.
24. Mertes, M. P.; Borne, R. F.; Hare, L. E. Synthesis of 3-pyridoxyalkanoic acids and their derivatives. J. Heterocycl. Chem. 1968, 5, 281-283.
25. Leo, D. G.; Brown, K. C.; Karaman, H. Oxidation of hydrocarbons. 17. Solvent and substituent effects on the oxidation of styrene derivatives by quaternary ammonium permanganates. Can. J. Chem. 1986, 64, 1054-1059.
26. Weller, D. D.; Stirchak, E. P.; Weller, D. L. Synthesis of 3-methyl-5,6-dihydro-3H-benzofuro[3,2-e]isoquinolin-7(7a)H-ones. J. Org. Chem. 1983, 48, 4597-4605.
27. Katritzky, A. R. An attempt to simulate the biogenesis of strychnine. Part I. Experiments with 4-(2′-aminomethyl)pyridine. J. Chem. Soc. 1955, 2581-2586.
28. Ohta, M.; Masaki, M. Mesoionic compounds. X. Syntheses of 4-substituted 3-(β-pyridyl)sydnones. Bull. Chem. Soc. Jpn. 1960, 33, 649-651.
29. McKay, A. F.; Bryce, J. R. G.; Rivington, D. E. Preparation and nitration of 1-sustituted-2-nitramino-2-imidazolines. Can. J. Chem. 1951, 29, 382-390.
30. Galat, A. A synthesis of α,β-unsaturated esters. J. Am. Chem. Soc. 1946, 68, 376-377.
31. Augeri, D. J.; O'Connor, S. J.; Janowick, D.; Szczepankiewicz, B.; Sullivan, G.; Larsen, J.; Kalvin, D.; Cohen, J.; Devine, E.; Zhang, H.; Cherian, S.; Saeed, B.; Ng, S.-C.; Rosenberg, S. Potent and selective noncysteine-containing inhibitors of protein farnesyltransferase. J. Med. Chem. 1998, 41, 4288-4300.
32. 3H]nicotine binding to mouse brain homogenate. J. Pharm. Pharmacol. 1988, 40, 793-797.
33. Dukat, M.; Fiedler, W.; Dumas, D.; Damaj, I.; Martin, B.; Rosecrans, J. A.; James, R. J.; Glennon, R. A. Pyrrolidine-modified and 6-substituted analogues of nicotine: A structure-affinity investigation. Eur. J. Med. Chem. 1996, 31, 875-888.
34. Munson, P. J.; Rodbard, D. Ligand: a versatile computerized approach for characterization of ligand-binding system. Anal. Biochem. 1980, 107, 220-239.
35. 50) of an enzymatic reaction. Biochem. Pharmacol. 1973, 22, 3099-3108.
36. Dewey, W. L.; Harris, L. S.; Howes, J. S.; Nuite, J. A. The effect of various neurohormonal modulations on the activity of morphine and the narcotic antagonists in tail-flick and phenylquinone test. J. Pharmacol. Exp. Ther. 1970, 175, 435-442.
37. Hylden, J. L.; Wilcox, G. L. Intrathecal morphine in mice: A new technique. Eur. J. Pharmacol. 1980, 67, 313-316.