5-[4-(Benzyloxy)phenyl]-1,3,4-oxadiazol-2(3H)-one Derivatives and Related Analogues: New Reversible, Highly Potent, and Selective Monoamine Oxidase Type B Inhibitors

Journal of Medicinal Chemistry

Volumn 36, Issue 9, 1993, Pages 1157-1167

  Mazouz, Fathi ^a   Gueddari, Salah ^a   Burstein, Claude ^a   Mansuy, Daniel ^b   Milcent, René ^a  

^a UNIVERSITÉ PARIS DESCARTES   (France)

^b UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

5 [4 (BENZYLOXY)PHENYL] 1,3,4 OXADIAZOL 2(3H) ONE; 5 [4 (BENZYLOXY)PHENYL] 1,3,4 OXADIAZOLE 2(3H) THIONE; 5 [4 (BENZYLOXY)PHENYL] 3 (2 CYANOETHYL) 1,3,4 OXADIAZOL 2(3H) ONE; 5 [4 (BENZYLOXY)PHENYL] 3 (2 HYDROXYETHYL) 1,3,4 OXADIAZOL 2(3H) ONE; MONOAMINE OXIDASE INHIBITOR; OXADIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; COMPETITIVE INHIBITION; DRUG MECHANISM; DRUG SELECTIVITY; ENZYME ACTIVITY; INHIBITION KINETICS; NERVE DEGENERATION; NONHUMAN; PARKINSON DISEASE; PRIORITY JOURNAL; RAT; STRUCTURE ACTIVITY RELATION; SYNAPTIC TRANSMISSION;

ANIMAL; BINDING, COMPETITIVE; BRAIN; KINETICS; MALE; MITOCHONDRIA; MOLECULAR STRUCTURE; MONOAMINE OXIDASE INHIBITORS; OXADIAZOLES; RATS; RATS, SPRAGUE-DAWLEY; STRUCTURE-ACTIVITY RELATIONSHIP; SUPPORT, NON-U.S. GOV'T;

EID: 0027175990     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00061a006     Document Type: Article

References (42)

1. Kearney, E. B.; Salach, J. I.; Walker, W. H.; Seng, R. L.; Kenney, W.; Zeszotek, E.; Singer, T. 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. 1971, 24, 321–327.
2. Greenawalt, J. W. Localization of monoamine oxidase in rat liver mitochondria. Adv. Biochem. Psychopharmacol. 1972, 5, 207–226.
3. Johnston, J. P. Some observations upon a new inhibitor of monoamine oxidase in brain tissue. Biochem. Pharmacol. 1968, 17, 1285–1297.
4. Knoll, J.; Magyar, K. Some puzzling pharmacological effects of monoamine oxidase inhibitors. Adv. Biochem. Psychopharmacol. 1972, 5, 393–408.
5. Dostert, P.; Strohn Benedetti, M.; Tipton, K. F. Interactions of monoamine oxidase with substrates and inhibitors. Med. Res. Rev. 1989, 9, 45–89.
6. Strohn Benedetti, M.; Dostert, P.; Tipton, K. F. Contributions of monoamine oxidase to the metabolism of xenobiotics. Prog. Drug. Metab. 1988, 11, 149–174.
7. Bach, A. J. W.; Lan, N. C.; Johnson, D. L.; Abell, C. W.; Bembenek, M. E.; Kwan, S. W.; Seeburg, P.; Shih, J. C. cDNA cloning of human liver monoamine oxidase A and B: Molecular basis of differences in enzymatic properties. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 4934–4938.
8. For review, see: Chen, S. Molecular basis of human MAO A and B Neuropsychopharmacology 1991, 4, 1–7.
9. Strohn Benedetti, M.; Dostert, P. Monoamine oxidase, brain ageing and degenerative diseases. Biochem. Pharmacol. 1989, 38, 555–561.
10. Cesura, A. M.; Pletscher, A. The new generation of monoamine oxidase inhibitors. Prog. Drug Res. 1992, 38, 171–297.
11. Richards, J. G.; Saura, J.; Ulrich, J.; Da Prada, M. Molecular neuroanatomy of monoamine oxidases. Psychopharmacoly 1992, 106 (Suppl.), 21–23.
12. Olanov, C. W. Oxidation reactions in Parkinson's disease. Neurotomy 1990, 40 (Suppl. 3), 32–39.
13. Riederer, G. P.; Jellinger, K. Neurochemical insights into monoamine oxidase inhibitors, with special reference to deprenyl (selegeline). Acta Neurol. Scand. 1983, 95, 43–55.
14. Birkmayer, W.; Birkmayer, G. J. Strategy and tactic of modern Parkinson therapy. Acta Neurol. Scand. 1989, 126 (Suppl.), 171–175.
15. Parkinson Study Group. DATATOP: A multicenter controlled clinical trial in Parkinson's disease. Arch. Neurol. 1989, 46, 1052–1060.
16. Langston, J. W. Selegeline as neuroprotective therapy in Parkinson's disease. Neurology 1990, 40 (Suppl. 3), 61–66.
17. The Parkinson Study Group. Effect of the progression of disability in early Parkinson's disease. N. Engl. J. Med. 1990, 322, 1526–1528.
18. Strolin Benedetti, M.; Dostert, P. Monoamine oxidase: From physiology and pathophysiology to the design and clinical application of reversible inhibitors. Adv. Drug Res. 1992, 23, 65–125.
19. Youdim, M. B. H.; Finberg, J. P. M. MAO type B inhibitors as adjunct to L-DOPA therapy. Adv. Neurol. 1986, 45, 127–136.
20. Zreika, M.; McDonald, I. A.; Bey, P.; Palfreyman, M. G. MDL 72,145, an enzyme-activated irreversible inhibitor with selectivity for monoamine oxidase B. J. Neurochem. 1984, 43, 448–454.
21. Zreika, M.; Fozard, J. R.; Dudley, M. W.; Bey, P.; McDonald, I. A.; Palfreyman, M. G. MDL 72,974: A potent and selective enzyme-activated irreversible inhibitor of monoamine oxidase type B with potential for use in Parkinson's disease. J. Neural. Trans. (P-D Sec) 1989, 1, 243–254.
22. Haefely, W. E.; Kettler, R.; Keller, H. H.; Da Prada, M. Ro 19-6327, a reversible and highly selective monoamine oxidase B inhibitor: A novel tool to explore the MAO B function in humans. Adv. Neurol. 1990, 53, 505–512.
23. Delini-Stula, A.; Radeke, E.; Waldmeier, P. C. Basic and clinical aspects of the new monoamine oxidase inhibitors. Psychopharmacol. Ser. 1988, 5, 147–158.
24. Da Prada, M.; Kettler, R.; Keller, H. H.; Bonetti, E. P.; Imhof, R. Ro 16-6491, a new reversible and highly selective MAO-B inhibitor protects mice from the dopaminergic neurotoxicity of MPTP. Adv. Neurol. 1986, 45, 175–178.
25. Mazouz, F.; Lebreton, L.; Milcent, R.; Burstein, C. 5-Aryl-1,3,4-oxadiazol-2(3H)-one derivatives and sulfur analogues as new selective and competitive monoamine oxidase type B inhibitors. Eur. J. Med. Chem. 1990, 25, 659–671.
26. Mazouz, F.; Lebreton, L.; Milcent, R.; Burstein, C. Inhibition of monoamine oxidase types A and B by 2-Aryl-4H-1,3,4-oxadiazin-5(6H)-one derivatives. Eur. J. Med. Chem. 1988, 23, 441–451.
27. Sherman, W. R. 5-Nitro-2-furyl-substituted 1,3,4-oxadiazoles, 1,3,4-thiadiazoles, and 1,3,5-triazines. J. Org. Chem. 1961, 26, 88–95.
28. Van Alphen, J. 1,3,4-Oxadiazines, IV. Recl. Trav. Chim. 1929, 48, 417–421.
29. Kjaer, A. Thiobenzoylation of esters and amides of a-amino acids. Acta Chem. Scand. 1950, 4, 1347–1350.
30. Feiner, A. F.; Waldmeier, P. C. Cumulative effects of irreversible MAO inhibitors in vivo. Biochem. Pharmacol. 1979, 28, 995–1002.
31. Kyburz, E. New developments in the field of monoamine oxidase inhibitors (MAO-I). In Trends in Medicinal Chemistry, Van der Goot, H., Domany, G., Pallos, L., Timmerman, H., Eds.; Elsevier: Amsterdam, 1988; pp 523–542.
32. Silverman, R. B. The use of mechanism based inactivators to probe the mechanism of monoamine oxidase. Biochem. Soc. Trans. 1991, 19, 201–206.
33. Cha, S. Tight-binding inhibitora-I. Biochem. Pharmacol. 1975, 24, 2177–2185.
34. Morrison, J. F.; Walsh, C. T. The behaviour and significance of slow-binding enzyme inhibitors. Adv. Enzym. 1988, 61, 201–301.
35. Henderson, P. J. A linear equation that describes the steady-state kinetics of enzymes and subcellular particules interacting with tightly bound inhibitors. Biochem. J. 1972, 127, 321–33.
36. Arai, Y.; Kinemuchi, H. Differences between MAO concentrations in striatum and forebrain of aged and young rats. J. Neural. Transm. 1988, 72, 99–105.
37. McDaniel, D. H.; Smoot, C. R. Approximations in the kinetics of consecutive reactions. J. Phys. Chem. 1956, 60, 966–969.
38. Oreland, L.; Hiraga, Y.; Jossan, S. S.; Regland, B.; Gottfries, C. G. Increased monoamine oxidase activity and vitamin B-12 deficiency in dementia disorders. In The Early Markers in Parkinson's and Alzheimer's Diseases; Dostert, P., Riederer, P., Strohn Benedetti, M., Roncucci, R., Eds.; Springer-Verlag: Wien, New York, 1990; pp 267–286.
39. Baggaley, K. H.; Fears, R.; Hindley, R. M.; Morgan, B.; Murrell, E.; Thome, D. E. Hypolipidemic analogues of ethyl 4-benzylox-ybenzoate. J. Med. Chem. 1977, 20, 1388–1393.
40. Hoffmann, U.; Jacobi, B. Amino nitriles and their conversion products. Ger. Patent 1934, 598,185; Chem. Abstr. 1934, 28, 5473–9.
41. Lowry, O. H.; Rosebrough, N. J.; Farr, A. L.; Randall, R. J. Protein measurement with the Folin phenol reagent. J. Biol. Chem. 1951, 193, 265–275.
42. Strolin Benedetti, M.; Dostert, P.; Guffroy, C.; Tipton, K. F. Partial or total protection from long-acting monoamine oxidase inhibitors (MAOIs) by new short-acting MAOs type A MD 780515 and type B MD 780236. Mod. Probl. Pharmacopsychiatry 1983, 19, 82–104.