Synthesis and biological evaluation of enantiomerically pure pyrrolyloxazolidinones as a new class of potent and selective monoamine oxidase type A inhibitors

Farmaco

Volumn 58, Issue 3, 2003, Pages 231-241

  Mai, A ^a   Artico, Marino ^a   Esposito, M ^a   Ragno, R ^a   Sbardella, G ^b   Massa, S ^c  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b UNIVERSITY OF SALERNO   (Italy)

^c UNIVERSITY OF SIENA   (Italy)

Author keywords

Antimycobacterial agents; MAO; MAO inhibitors; Oxazolidinones

Indexed keywords

2 OXAZOLIDINONE DERIVATIVE; 5 AZIDOMETHYL 3 (1 METHYL 1H PYRROL 2 YL) 2 OXAZOLIDINONE; 5 HYDROXYMETHYL 3 (1H PYRROL 1 YL) 2 OXAZOLIDINONE; 5 METHOXYMETHYL 3 (1H PYRROL 1 YL) 2 OXAZOLIDINONE; 5 METHYLAMINO 3 (1 BENZYL 1H PYRROL 2 YL) 2 OXAZOLIDINONE; ANTIMYCOBACTERIAL AGENT; BEFLOXATONE; ETHAMBUTOL; LINEZOLID; MONOAMINE OXIDASE A INHIBITOR; PYRAZINAMIDE; STREPTOMYCIN; TOLOXATONE; U 100480; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIAL STRAIN; CONTROLLED STUDY; DRUG ACTIVITY; DRUG EFFECT; DRUG POTENCY; DRUG SCREENING; DRUG SELECTIVITY; DRUG SYNTHESIS; ENANTIOMER; ENZYME ACTIVITY; ENZYME INHIBITION; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM AVIUM; MYCOBACTERIUM SMEGMATIS; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN;

EID: 0037373722     PISSN: 0014827X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0014-827X(03)00016-8     Document Type: Article

References (41)

1. Shih J.C., Chen K., Ridd M.J. Monoamine oxidase: from genes to behavior. Annu. Rev. Neurosci. 22:1999;197-217.
2. Shih J.C., Thompson R.F. Monoamine oxidase in neuropsychiatry and behavior. Am. J. Hum. Genet. 65:1999;593-598.
3. Chiba K., Trevor A., Castagnoli N. Metabolism of the neurotoxic tertiary amine, MPTP, by brain monoamine oxidase. Biochem. Biophys. Res. Commun. 120:1984;574-578.
4. Fritz R.R., Abell C.W., Patel N.T., Gessner W., Brossi A. Metabolism of the neurotoxin in MPTP by human liver monoamine oxidase B. FEBS Lett. 186:1985;224-228.
5. Grimsby J., Toth M., Chen K., Kumazawa T., Klaidman L., Adams J.D., Karoum F., Gal J., Shih J.C. Increased stress response and beta-phenylethylamine in MAOB-deficient mice. Nat. Genet. 17:1997;206-210.
6. De Zutter G.S., Davis R.J. Pro-apoptotic gene expression mediated by the p38 mitogen-activated protein kinase signal transduction pathway. Proc. Natl. Acad. Sci. USA. 98:2001;6168-6173.
7. Bach A.W.J., Lan N.C., Johnson D.L., Abell C.W., Bembenek M.E., Kwan S.-W., Seeburg P.H., Shih J.C. cDNA cloning of human liver monoamine oxidase A and B: molecular basis of differences in enzymatic properties. Proc. Natl. Acad. Sci. USA. 85:1988;4934-4938.
8. Johnston J.P. Some observations upon a new inhibitor of monoamine oxidase in brain tissue. Biochem. Pharmacol. 17:1968;1285-1297.
9. Kalgutkar A.S., Castagnoli N. Jr., Testa B. Selective inhibitors of monoamine oxidase (MAO-A and MAO-B) as probes of its catalytic site and mechanism. Med. Res. Rev. 15:1995;325-388.
10. Westlund R.N., Denney R.M., Kochersperger L.M., Rose R.M., Abell C.W. Distinct monoamine oxidase A and B populations in primate brain. Science. 230:1985;181-183.
11. Knoll J., Magyar K. Some puzzling pharmacological effects of monoamine oxidase inhibitors. Adv. Biochem. Psycopharmacol. 5:1972;393-408.
12. Kearney E.B., Salach J.I., Walker W.H., Seng R.L., Kenny W., Zeszotek E., Singer T.P. The covalently bound flavin of hepatic monoamine oxidase. Isolation and sequence of a flavin peptide and evidence of a binding at the 8-a position. Eur. J. Biochem. 24:1971;321-327.
13. Yu P.H. Studies on the pargyline-binding site of different types of monoamine oxidase. Can. J. Biochem. 59:1981;30-37.
14. Wu H.F., Chen K., Shih J.C. Site-directed mutagenesis of monoamine oxidase A and B: role of cysteines. Mol. Pharmacol. 43:1993;888-893.
15. Wouters J. Structural aspects of monoamine oxidase and its reversible inhibition. Curr. Med. Chem. 5:1998;137-162.
16. Grimsby J., Chen K., Wang L.-J., Lan N.C., Shih J.C. Human monoamine oxidase A and B genes exhibit identical exon-intron organization. Proc. Natl. Acad. Sci. USA. 88:1991;3637-3641.
17. Brunner H.G., Nelen M., Breakfield X.O., Ropers H.H., Van Oost B.A. Abnormal behavior associated with a point mutation in the structural gene for monoamine oxidase A. Science. 262:1993;578-580.
18. Cases O., Seif I., Grimsby J., Gaspar P., Chen K., Pournin S., Muller U., Aguet M., Babinet C., Shih J.C., De Maeyer E. Aggressive behavior and altered amounts of brain serotonin and norepinephrine in mice lacking MAO A. Science. 268:1995;1763-1766.
19. Tyrer P., Shawcross C. Monoamine oxidase inhibitors in anxiety disorders. J. Psychiatr. Res. Suppl. 1:1988;87-98.
20. Malorni W., Gianmmorioli A.M., Matarrese P., Pietrangeli P., Agostinelli E., Ciaccio A., Grassili E., Mondovì B. Protection against apoptosis by monoamine oxidase A inhibitors. FEBS Lett. 426:1998;155-159.
21. Knoll J., Ecsery Z., Kelemen K., Nievel J., Knoll B. Phenylisopropylmethyl-propinylamine (E-250), a new psychic energizer. Arch. Int. Pharmachodyn. Ther. 155:1965;154-164.
22. Tetrud J.W., Langston J.W. The effect of deprenyl (selegiline) on the natural history of Parkinson's disease. Science. 245:1989;519-522.
23. Cesura A.M., Pletscher A. The new generation of monoamine oxidase inhibitors. Prog. Drug Res. 38:1992;171-257.
24. Strolin-Benedetti M., Dostert P. Monoamine oxidase: from physiology and pathophysiology to the design and clinical application of reversible inhibitors. Adv. Drug Res. 23:1992;65-125.
25. Da Prada M., Kettler R., Keller H.H., Burkard W.P., Muggli-Maniglio D., Haefely W.E. Neurochemical profile of moclobemide, a short-acting and reversible inhibitor of monoamine oxidase type A. J. Pharmacol. Exp. Ther. 248:1989;400-414.
26. Waldmeier P.C., Felner A.E., Tipton K.F. The monoamine oxidase inhibiting properties of CGP 11305 A. Eur. J. Pharmacol. 94:1983;73-83.
27. Da Prada M., Kettler R., Keller H.H., Cesura A.M., Richards J.G., Saura Marti J., Muggli-Maniglio D., Wyss P.-C., Kyburz E., Imhof R. From moclobemide to Ro 19-6327 and Ro 41-1049: the development of a new class of reversible, selective MAO-A and MAO-B inhibitors. J. Neural Transm. [Suppl.]. 29:1990;279-292.
28. Dostert P., Strolin-Benedetti M., Tipton K.F. Interactions of monoamine oxidase with substrates and inhibitors. Med. Res. Rev. 9:1989;45-89.
29. Kan J.-P., Pujol J.-F., Malnoe A., Strolin-Benedetti M., Gouret C., Raynaud G. Effects of a new antidepressant (3-methyl)-3-phenyl-5-hydroxymethyl-2-oxazolidinone (toloxatone) upon 5-hydroxytryptamine pathways. Eur. J. Med. Chem.-Chim. Ther. 12:1977;13-16.
30. Moureau F., Wouters J., Vercauteren D.P., Collin S., Evrard G., Durant F., Ducrey F., Koenig J.J., Jarreau F.X. A reversible monoamine oxidase inhibitor, toloxatone: structural and electronic properties. Eur. J. Med. Chem. 27:1992;939-948.
31. Moureau F., Wouters J., Vercauteren D.P., Collin S., Evrard G., Durant F., Ducrey F., Koenig J.J., Jarreau F.X. A reversible monoamine oxidase inhibitor, Toloxatone: spectrophotometric and molecular orbital studies of the interaction with flavin adenine dinucleotide (FAD). Eur. J. Med. Chem. 29:1994;269-277.
32. Moureau F., Wouters J., Depas M., Vercauteren D.P., Durant F., Ducrey F., Koenig J.J., Jarreau F.X. A reversible monoamine oxidase inhibitor, Toloxatone: comparison of its physicochemical properties with those of other inhibitors including Brofaromine, Harmine, R40519 and Moclobemide. Eur. J. Med. Chem. 30:1995;823-838.
33. Rabasseda X., Sorbera L.A., Castaner J. Befloxatone. Drugs Fut. 24:1999;1057-1067.
34. Wouters J., Moureau F., Evrard G., Koenig J.J., Jegham S., George P., Durant F. A reversible monoamine oxidase A inhibitor, Befloxatone: structural approach of its mechanism of action. Bioorg. Med. Chem. 7:1999;1683-1693.
35. P. Dostert, C. Douzon, G. Bourgery, C. Gouret, G. Mocquet, J.A. Coston, 3-Aryl-2-oxazolidinones (Delalande S.A., Fr.). Ger. Offen. DE 2708236, 1977.
36. Massa S., Mai A., Corelli F. Synthesis of new tetracyclic system related to aptazapine (CGS 7525A) by one-pot double annalation. Tetrahedron Lett. 29:1988;6471-6474.
37. Massa S., Mai A., Artico M., Corelli F., Botta M. Synthesis of 3b,4,6,7-tetrahydro-5H,9H-pyrazino[2,1-c]pyrrolo[1,2-a][1,4]benzodiazepine, a valuable precursor of potential central nervous system agents. Tetrahedron. 45:1989;2763-2772.
38. Massa S., Artico M., Mai A., Corelli F., Botta M., Tafi A., Pantaleoni G.C., Giorgi R., Coppolino M.F., Cagnotto A., Skorupska M. Pyrrolobenzodiazepines and related systems. 2. Synthesis and biological properties of isonoraptazepine derivatives. J. Med. Chem. 35:1992;4533-4541.
39. Mai A., Di Santo R., Massa S., Artico M., Pantaleoni G.C., Giorgi R., Coppolino M.F., Barracchini A. Pyrrolobenzodiazepines with antinociceptive activity: synthesis and pharmacological activities. Eur. J. Med. Chem. 30:1995;593-601.
40. Diekema D.J., Jones R.N. Oxazolidinones. A review. Drugs. 59:2000;7-16.
41. J.C. Hamel, D. Stapert, J.K. Moerman, C.W. Ford, Linezolid, Critical Characteristics, Infection 28 (2000) 60-64.