Sulfur-substituted α-alkyl phenethylamines as selective and reversible MAO-A inhibitors: Biological activities, CoMFA analysis, and active site modeling

Journal of Medicinal Chemistry

Volumn 48, Issue 7, 2005, Pages 2407-2419

  Gallardo Godoy, Alejandra ^a,d   Fierro, Angélica ^b   McLean, Thomas H ^d   Castillo, Mariano ^a   Cassels, Bruce K ^a,c   Reyes Parada, Miguel ^b   Nichols, David E ^d  

^a UNIVERSITY OF CHILE   (Chile)

^b UNIVERSIDAD DE SANTIAGO DE CHILE   (Chile)

^c UNIVERSIDAD ANDRÉS BELLO   (Chile)

^d PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 (2 CHLORO 4,6 DIMETHOXYPHENYL) 2 AMINOPROPANE; 1 (2,5 DIMETHOXY 4 N PROPYLTHIOPHENYL) 2 AMINOPROPANE; 1 (2,6 DIMETHOXY 4 ETHYLTHIOPHENYL) 2 AMINOPROPANE; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME A; CLORGYLINE; MONOAMINE OXIDASE A INHIBITOR; PHENETHYLAMINE DERIVATIVE; PROPYLAMINE; SULFUR DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; CRYSTAL STRUCTURE; DRUG DESIGN; DRUG POTENCY; ENZYME ACTIVE SITE; ENZYME ASSAY; ENZYME INHIBITION; METHYLATION; MOLECULAR MODEL; PROTON NUCLEAR MAGNETIC RESONANCE; PSYCHOPHARMACOLOGY;

ANIMALS; BINDING SITES; BRAIN; CLORGYLINE; CRYSTALLOGRAPHY, X-RAY; MALE; METHYLATION; MITOCHONDRIA; MODELS, MOLECULAR; MONOAMINE OXIDASE; MONOAMINE OXIDASE INHIBITORS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RATS; RATS, SPRAGUE-DAWLEY;

EID: 17144432232     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0493109     Document Type: Article

References (37)

1. Nichols, D. E.; Marona-Lewicka, D.; Huang, X.; Johnson, M. P. Novel serotonergic agents. Drug Des. Discovery 1993, 9, 299-312.
2. Nichols, D. E. Medicinal Chemistry and Structure-Activity Relationships. In Amphetamine and Its Analogues; Psychopharmacology, Toxicology, and Abuse.; Cho, A. K. a. S. D. S., Ed.; Academic Press: San Diego, CA, 1994; pp 3-41.
3. Nichols, D. E. Hallucinogens. Pharmacol. Ther. 2004, 101, 131-181.
4. Johnston, J. P. Some observations upon a new inhibitor of monoamine oxidase in brain tissue. Biochem. Pharmacol. 1988, 17, 1285-1297.
5. Nagatsu, T. Progress in monoamine oxidase (MAO) research in relation to genetic engineering. Neurotoxicology 2004, 25, 11-20.
6. Shih, J. C. Cloning, after cloning, knock-out mice, and physiological functions of MAO A and B. Neurotoxicology 2004, 25, 21-30.
7. Yamada, M.; Yasuhara, H. Clinical pharmacology of MAO inhibitors: safety and future. Neurotoxicology 2004, 25, 215-221.
8. Youdim, M. B.; Weinstock, M. Therapeutic applications of selective and nonselective inhibitors of monoamine oxidase A and B that do not cause significant tyramine potentiation. Neurotoxicology 2004, 25, 243-250.
9. Gerlach, M.; Double, K.; Reichmann, H.; Riederer, P. Arguments for the use of dopamine receptor agonists in clinical and preclinical Parkinson's disease. J. Neural Transm. Suppl. 2003, 167-183.
10. Riederer, P.; Danielczyk, W.; Grunblatt, E. Monoamine oxidase-B inhibition in Alzheimer's disease. Neurotoxicology 2004, 25, 271-277.
11. Scorza, M. C.; Carrau, C.; Silveira, R.; Zapata-Torres, G.; Cassels, B. K.; Reyes-Parada, M. Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives: structure-activity relationships. Biochem. Pharmacol. 1997, 54, 1361-1369.
12. Florvall, L.; Ask, A. L.; Ogren, S. O.; Ross, S. B. Selective monoamine oxidase inhibitors. 1. Compounds related to 4-aminophenethylamine. J. Med. Chem. 1978, 21, 56-63.
13. Ask, A. L.; Fagervall, I.; Florvall, L.; Ross, S. B.; Ytterborn, S. Inhibition of monoamine oxidase in 5-hydroxytryptaminergic neurones by substituted p-aminophenylalkylamines. Br. J. Pharmacol. 1985, 85, 683-690.
14. Arai, Y.; Kim, S. K.; Kinemuchi, H.; Tadano, T.; Satoh, S. E.; Satoh, N.; Kisara, K. Inhibition of brain type A monoamine oxidase and 5-hydroxytryptamine uptake by two amphetamine metabolites, p-hydroxyamphetamine and p-hydroxynorephedrine. J. Neurochem. 1990, 55, 403-408.
15. Green, A. L.; El Hait, M. A. p-Methoxyamphetamine, a potent reversible inhibitor of type-A monoamine oxidase in vitro and in vivo. J. Pharm. Pharmacol. 1980, 32, 262-266.
16. Ma, J.; Yoshimura, M.; Yamashita, E.; Nakagawa, A.; Ito, A.; Tsukihara, T. Structure of rat monoamine oxidase A and its specific recognitions for substrates and inhibitors. J. Mol. Biol. 2004, 338, 103-114.
17. Shulgin, A. T.; Shulgin, A. PIHKAL a chemical love story; Transform Press: Berkeley, CA, 1992.
18. Jacob, P., III; Anderson, G., III; Meshul, C. K.; Shulgin, A. T.; Castagnoli, N., Jr. Monomethylthio analogues of 1-(2,4,5-trimethoxyphenyl)-2- aminopropane. J. Med. Chem. 1977, 20, 1235-1239.
19. Maillard, J.; Vincent, M.; Delaunay, P.; Fumeron, B. Derivatives of phloroglucinol. Synthesis and acetylacion of mono-, di- and triethers of mono- and dichloro-2,4,6-trihydroxybenzoic acid. Bull. Soc. Chim. Fr. 1966, 8, 2520-2524.
20. Newman, M. S.; Karnes, H. K. The conversion of phenols to thiophenols via dialkylthiocarbamates. J. Org. Chem. 1966, 31, 3980-3984.
21. Kwart, H.; Evans, E. R. The vapor phase rearrangement of thioncarbonates and thioncarbamates. J. Org. Chem. 1966, 31, 410-413.
22. Reyes-Parada, M.; Scorza, M. C.; Silveira, R.; Dajas, F.; Cassels, B. K. 4-Dimethylaminophenetnylamine, a sensitive, specific, electrochemically detectable monoamine oxidase-B substrate. Life Sci. 1994, 54, 1955-1963.
23. Hurtado-Guzman, C.; Fierro, A.; Iturriaga-Vasquez, P.; Sepulveda-Boza, S.; Cassels, B. K.; Reyes-Parada, M. Monoamine oxidase inhibitory properties of optical isomers and N-substituted derivatives of 4-methylthioamphetamine. J. Enzyme Inhib. Med. Chem. 2003, 18, 339-347.
24. Lowry, O.; Rosebrough, N.; Farr, A.; Randall, R. Protein measurement with the Folin phenol reagent. J. Biol. Chem. 1951, 193, 265-275.
25. Tripos, Inc., 1699 S. Hanley Rd., St. Louis, MO 63144. SYBYL 6.9, 2004.
26. Mantle, T. J.; Tipton, K. F.; Garrett, N. J. Inhibition of monoamine oxidase by amphetamine and related compounds. Biochem. Pharmacol. 1976, 25, 2073-2077.
27. Robinson, J. B. Stereoselectivity and isoenzyme selectivity of monoamine oxidase inhibitors. Enantiomers of amphetamine, N-methylamphetamine and deprenyl. Biochem. Pharmacol. 1985, 34, 4105-4108.
28. Egashira, T.; Yamanaka, Y. Changes in monoamine oxidase activity in mouse brain associated with d-methamphetamine dependence and withdrawal. Biochem. Pharmacol. 1993, 46, 609-614.
29. Roman, D. L.; Saldana, S. N.; Nichols, D. E.; Carroll, F. I.; Barker, E. L. Distinct molecular recognition of psychostimulants by human and Drosophila serotonin transporters. J. Pharmacol. Exp. Ther. 2004, 308, 679-687.
30. DeLano Scientific, PyMOL, 2004.
31. Nichols, D. E.; Shulgin, A. T. Sulfur analogs of psychotomimetic amines. J. Pharm. Sci. 1976, 65, 1554-1556.
32. Caroli-Rezende, M.; Núñez, C.; Sepúlveda-Boza, S.; Cassels, B. K.; Hurtado-Guzmán, C. S-oxidation products of alkylthio-amphetamines. Synth. Commun. 2002, 32, 2741-2750.
33. Kuliev, A. M.; Gyul'akhmedov, L. M.; Kuliev, A. B.; Zeinalova, G. A. Synthesis of some derivatives of 2,5-dimethoxythiophenol. J. Org. Chem. USSR (Engl. Transl.) 1969, 5, 1760-1762.
34. Sindelar, K.; Holubek, J.; Svatek, E.; Schlanger, J.; Dlabac, A.; Valchar, M.; Hrubantova, M.; Protiva, M. Open-ring models of hetero-cannabinoids: synthesis of 2-(alkylthio)-5-(2-aminoethyl)-hydroquinone derivatives. Coll. Czech. Chem. Commun. 1990, 55, 782-796.
35. Standridge, R. T.; Howell, H. G.; Tilson, H. A.; Chamberlain, J. H.; Holava, H. M.; Gylys, J. A.; Partyka, R. A.; Shulgin, A. T. Phenylalkylamines with potential psychotherapeutic utility. 2. Nuclear substituted 2-amino-1-phenylbutanes. J. Med. Chem. 1980, 23, 154-162.
36. Wolfers, H.; Kraatz, U.; Korte, F. New route to 1-alkylthio-3,5- dihydroxybenzenes (monothiophloroglucinol-S-alkyl ethers). Synthesis 1975, 1, 43-44.
37. Sargent, M. V. Reaction of some 1,4-benzoquinone monooximes with methanolic hydrogen chloride. Journal of the Chemical Society, Perkin Transaction 1: Org. Bio-Org. Chem. 1982, 4, 1095-1098.