Synthesis and Selective Inhibitory Activity of 1-Acetyl-3,5-diphenyl-4,5-dihydro-(1H)-pyrazole Derivatives against Monoamine Oxidase

Journal of Medicinal Chemistry

Volumn 47, Issue 8, 2004, Pages 2071-2074

  Chimenti, Franco ^a   Bolasco, Adriana ^a   Manna, Fedele ^a   Secci, Daniela ^a   Chimenti, Paola ^a   Befani, Olivia ^a   Turini, Paola ^a   Giovannini, Valentina ^a   Mondovì, Bruno ^a   Cirilli, Roberto ^b   La Torre, Francesco ^b  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b ISTITUTO SUPERIORE DI SANITÀ   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1 ACETYL 3,5 DIPHENYL 4,5 DIHYDRO (1H) PYRAZOLE DERIVATIVE; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME A; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME B; MONOAMINE OXIDASE INHIBITOR; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CHIRALITY; COMPARATIVE STUDY; CONTROLLED STUDY; DRUG POTENCY; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; ENZYME ACTIVITY; ENZYME INHIBITION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IC 50; IN VITRO STUDY; INHIBITION KINETICS; MELTING POINT; NONHUMAN; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

ANIMALS; BRAIN; CATTLE; ISOENZYMES; MITOCHONDRIA; MONOAMINE OXIDASE; MONOAMINE OXIDASE INHIBITORS; PYRAZOLES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 11144358502     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm031042b     Document Type: Article

References (23)

1. Mondovi, B. in Structure and function of amine oxidases; CRC Press: Boca Raton, FL, 1985.
2. Johnston, J. P. Some observations upon a new inhibitor of monoamine oxidase in brain tissue. Biochem. Pharmacol. 1968, 17, 1285-1297.
3. Weyler, W.; Hsu, Y. P.; Breakefield, O. Biochemistry and genetics of monoamine oxidase. Pharmacol. Ther. 1990, 47, 391-417.
4. Geha, R. M.; Rebrin, I.; Chen, K.; Shih, J. C. Substrate and inhibitor specificities for human monoamine oxidase A and B are influenced by a single amino acid. J. Biol. Chem. 2001, 276, 9877-9882.
5. Strolin-Benedetti, M.; Dostert, P. L. Monoamine oxidase: From physiology and pathophysiology to the design and clinical application of reversible inhibitors. Adv. Drug Res. 1992, 23, 65-125.
6. Youdim, M. B. H.; Finberg, J. P. M. New directions in monoamine oxidase A and B. Selective inhibitors and substrates. Biochem. Pharmacol. 1991, 41, 155-162.
7. Cesura, A. M.; Pletscher, A. The new generation of monoamine oxidase inhibitors. Prog. Drug Res. 1992, 38, 171-297.
8. Rudorfer, M. V.; Potter, W. Z. Antidepressants. A comparative review of the clinical pharmacology and therapeutic use of the "newer" versus the "older drugs". Drugs 1989, 37, 713-738.
9. Wouters, J. Structural aspects of monoamine oxidase and its reversible inhibition. Curr. Med. Chem. 1998, 5, 137-162.
10. Tetrud, J. W.; Langston, J. W. The effect of deprenyl (selegiline) on the natural history of Parkinson's disease. Science 1989, 245, 519-522.
11. Binda, C.; Newton-Vinson, P.; Hubálek, F.; Edmondson, D. E.; Mattevi, A. Structure of human monoamine oxidase B, a drug target for the treatment of neurological disorders. Nat. Struct. Biol. 2002, 9, 22-26.
12. Wouters, J.; Ooms, F.; Jegham, S.; Koenig, J. J.; George, P.; Durant, F. Reversible inhibition of type B monoamine oxidase. Theoretical study of model diazo heterocyclic compounds. Eur. J. Med. Chem. 1997, 32, 721-730.
13. 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. 1999, 7, 1683-1693.
14. Altomare, C.; Cellamare S.; Summo, L.; Catto, M.; Carotti, A. Inhibition of monoamine oxidase-B by condensed pyridazines and pyrimidines: effects of lipophilicity and structure-activity relationships. J. Med. Chem. 1998, 41, 3812-3820.
15. Parmar, S. S.; Pandey, B. R.; Dwivedi, C.; Harbison, R. D. Anticonvulsivant activity and monoamine oxidase inhibitory properties of 1,3,5-trisubstituted pyrazolines. J. Pharm. Sci. 1974, 63, 1152-1155.
16. Soni, N.; Pande, K.; Kalsi, R.; Kupta, K. T.; Parmar, S. S.; Barthwal, J. P. Inhibition of rat brain monoamine oxidase and succinic dehydrogenase by anticonvulsivant pyrazolines. Res. Commun. Chem. Pathol. Pharmacol. 1987, 56 (1), 129-132.
17. Palaska, E.; Erol, D.; Demirdamar, R. Synthesis and antidepressant activities of some 1,3,5-triphenyl-2-pyrazolines. Eur. J. Med. Chem. 1996, 31, 43-47.
18. Manna, F.; Chimenti F.; Bolasco, A.; Bizzarri, B.; Befani, O.; Pietrangeli, P.; Mondovì, B.; Turini, P. Inhibitory effect of 1,3,5-triphenyl-4,5-dihydro-(1H)-pyrazole derivatives on activity of amine oxidases. J. Enzyme Inhib. 1998, 13, 207-216.
19. Manna, F.; Chimenti, F.; Bolasco, A.; Secci, D.; Bizzarri, B.; Befani, O.; Mondovi, B.; Turini, P.; Alcaro, S.; Tafi, A. Inhibition of amine oxidases activity by 1-acetyl-3,5-diphenyl-4,5-dihydro-(1H)-pyrazole derivatives. Bioorg. Med. Chem. Lett. 2002, 12, 3629-3633.
20. Yashima, E.; Yamamoto, C.; Okamoto, Y. Polysaccharide-based chiral LC columns. Synlett. 1998, 344-360.
21. Basford, R. E. Preparation and properties of brain mitochondria. Methods Enzymol. 1967, 10, 96-101.
22. Matsumoto, T.; Suzuki, O.; Furuta T.; Asai, M.; Kurokawa, Y.; Rimura, Y. ; Katsumata, Y.; Takahashi, I. A sensitive fluorometric assay for serum monoamine oxidase with kynuramine as substrate. Clin. Biochem. 1985, 18, 126-129.
23. Bradford, M. M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 1976, 72, 248-254.