Synthesis, stereochemical separation, and biological evaluation of selective inhibitors of human MAO-B: 1-(4-Arylthiazol-2-yl)-2-(3- methylcyclohexylidene)hydrazines

Journal of Medicinal Chemistry

Volumn 53, Issue 17, 2010, Pages 6516-6520

  Chimenti, Franco ^a   Secci, Daniela ^a   Bolasco, Adriana ^a   Chimenti, Paola ^a   Granese, Arianna ^a   Carradori, Simone ^a   Yáñez, Matilde ^b   Orallo, Francisco ^b   Sanna, M Luisa ^c   Gallinella, Bruno ^c   Cirilli, Roberto ^c  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^c ISTITUTO SUPERIORE DI SANITÀ   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1 (4 ARYLTHIAZOL 2 YL) 2 (3 METHYLCYCLOHEXYLIDENE)HYDRAZINE DERIVATIVE; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME B; HYDRAZINE DERIVATIVE; MONOAMINE OXIDASE B INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; ENZYME ACTIVITY; ENZYME INHIBITION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IC 50; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYCLOHEXANES; HUMANS; HYDRAZINES; ISOENZYMES; MONOAMINE OXIDASE; MONOAMINE OXIDASE INHIBITORS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZOLES;

EID: 77956305471     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm100120s     Document Type: Article

References (29)

1. Edmondson, D. E.; Mattevi, A.; Binda, C.; Li, M.; Hubálek, F. Structure and mechanism of monoamine oxidase Curr. Med. Chem. 2004, 11, 1983-1993
2. Edmondson, D. E.; DeColibus, L.; Binda, C.; Li, M.; Mattevi, A. New insights into the structures and functions of human monoamine oxidases A and B J. Neural Transm. 2007, 114, 703-705
3. Edmondson, D. E.; Binda, C.; Wang, J.; Upadhayay, A. K.; Mattevi, A. Molecular and mechanistic properties of the membrane-bound mitochondrial monoamine oxidases Biochemistry 2009, 48, 4220-4230
4. Shih, J. C.; Chen, K.; Ridd, M. J. Monoamine oxidase: from genes to behaviour Annu. Rev. Neurosci. 1999, 22, 197-217
5. Shih, J. C.; Chen, K. Regulation of MAO-A and MAO-B gene expression Curr. Med. Chem. 2004, 11, 1995-2005
6. 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. 1990, 29, 279-292
7. Guay, D. R. Rasagiline (TVP-1012): a new selective monoamine oxidase inhibitor for Parkinson's disease Am. J. Geriatr. Pharmacother. 2006, 4 (4) 330-346
8. Son, S. Y.; Ma, J.; Kondou, Y.; Yoshimura, M.; Yamashita, E.; Tsukihara, T. Structure of human monoamine oxidase A at 2.2-Å resolution: the control of opening the entry for substrates/inhibitors Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 5739-5744. Data deposition: www.pdb.org (PDB ID code 2Z5X)
9. Hubálek, F.; Binda, C.; Khalil, A.; Li, M.; Mattevi, A.; Castagnoli, N.; Edmondson, D. E. Demonstration of isoleucine 199 as a structural determinant for the selective inhibition of human monoamine oxidase B by specific reversible inhibitors J. Biol. Chem. 2005, 280 (16) 15761-15766. Data deposition: www.pdb.org (PDB ID code 2BK3)
10. Mellick, G. D.; Buchanan, D. D.; McCann, S. J.; James, K. M.; Johnson, A. G.; Davis, D. R.; Liyou, N.; Chan, D.; Le Couteur, D. G. Variations in the monoamine oxidase B (MAO B) gene are associated with Parkinson's disease Mov. Disord. 1999, 14, 219-224
11. Riederer, P.; Lachenmayer, L.; Laux, G. Clinical applications of MAO-inhibitors Curr. Med. Chem. 2004, 11, 2033-2043
12. Youdim, M. B. H.; Edmondson, D. E.; Tipton, K. F. The therapeutic potential of monoamine oxidase inhibitors Nat. Rev. Neurosci. 2006, 7, 295-309
13. Bortolato, M.; Chen, K.; Shih, J. C. Monoamine oxidase inactivation: from pathophysiology to therapeutics Adv. Drug Delivery Rev. 2008, 60, 1527-1533
14. Carreiras, M. C.; Marco, J. L. Recent approaches to novel anti-Alzheimer therapy Curr. Pharm. Des. 2004, 10 (25) 3167-3175
15. Drukarch, B.; Muiswinkel, F. L. Drug treatment of Parkinson's disease Biochem. Pharmacol. 2000, 59, 1023-1031
16. Sayre, L. M.; Perry, G.; Smith, M. A. Oxidative stress and neurotoxicity Chem. Res. Toxicol. 2008, 21, 172-188
17. Blandini, F. Neuroprotection by rasagiline: a new therapeutic approach to Parkinson's disease CNS Drug Rev. 2005, 11, 183-194
18. Youdim, M. B.; Gross, A.; Finberg, J. P. Rasagiline [ N -propargyl-1 R (+)-aminoindan], a selective and potent inhibitor of mitochondrial monoamine oxidase B Br. J. Pharmacol. 2001, 132 (2) 500-506
19. Binda, C.; Hubálek, F.; Li, M.; Herzig, Y.; Sterling, J.; Edmondson, D. E.; Mattevi, A. Crystal structures of monoamine oxidase B in complex with four inhibitors of the N -propargylaminoindan class J. Med. Chem. 2004, 47, 1767-1774
20. Bolasco, A.; Fioravanti, R.; Carradori, S. Recent development of monoamine oxidase inhibitors Expert Opin. Ther. Pat. 2005, 15 (12) 1763-1782
21. Chimenti, F.; Maccioni, E.; Secci, D.; Bolasco, A.; Chimenti, P.; Granese, A.; Befani, O.; Turini, P.; Alcaro, S.; Ortuso, F.; Cardia, M. C.; Distinto, S. Selective inhibitory activity against MAO and molecular modeling studies of 2-thiazolylhydrazone derivatives J. Med. Chem. 2007, 50, 707-712
22. Chimenti, F.; Maccioni, E.; Secci, D.; Bolasco, A.; Chimenti, P.; Granese, A.; Carradori, S.; Alcaro, S.; Ortuso, F.; Yáñez, M.; Orallo, F.; Cirilli, R.; Ferretti, R.; La Torre, F. Synthesis, stereochemical identification, and selective inhibitory activity against human monoamine oxidase-B of 2-methylcyclohexylidene-(4-arylthiazol-2-yl)hydrazones J. Med. Chem. 2008, 51, 4874-4880
23. Chimenti, F.; Carradori, S.; Secci, D.; Bolasco, A.; Chimenti, P.; Granese, A.; Bizzarri, B. Synthesis and biological evaluation of novel conjugated coumarin-thiazole systems J. Heterocycl. Chem. 2009, 46 (3) 575
24. Chimenti, F.; Secci, D.; Bolasco, A.; Chimenti, P.; Granese, A.; Carradori, S.; D'Ascenzio, M.; Yáñez, M.; Orallo, F. Synthesis and selective inhibition of human monoamine oxidases of a large scaffold of (4,5-substituted-thiazol-2-yl)hydrazones Med. Chem. Commun. 2010, 1, 61-72
25. Cirilli, R.; Ferretti, R.; La Torre, F.; Secci, D.; Bolasco, A.; Carradori, S.; Pierini, M. High-performance liquid chromatographic separation of enantiomers and diastereomers of 2-methylcyclohexanone thiosemicarbazone, and determination of absolute configuration and configurational stability J. Chromatogr., A 2007, 1172, 160-169
26. Yáñez, M.; Fraiz, N.; Cano, E.; Orallo, F. Inhibitory effects of cis-and trans -resveratrol on noradrenaline and 5-hydroxytryptamine uptake and on monoamine oxidase activity Biochem. Biophys. Res. Commun. 2006, 344, 688-695
27. Li, M.; Binda, C.; Mattevi, A.; Edmondson, D. E. Functional role of the "aromatic cage" in human monoamine oxidase B: structures and catalytic properties of Tyr435 mutant proteins Biochemistry 2006, 45, 4775-4784
28. Chimenti, F.; Bizzarri, B.; Secci, D.; Bolasco, A.; Fioravanti, R.; Chimenti, P.; Granese, A.; Carradori, S.; Rivanera, D.; Lilli, D.; Zicari, A.; Distinto, S. Synthesis and in vitro activity of 2-thiazolylhydrazone derivatives compared with the activity of clotrimazole against clinical isolates of Candida spp Bioorg. Med. Chem. Lett. 2007, 17 (16) 4635-4640
29. Chimenti, F.; Bizzarri, B.; Maccioni, E.; Secci, D.; Bolasco, A.; Chimenti, P.; Fioravanti, R.; Granese, A.; Carradori, S.; Tosi, F.; Ballario, P.; Vernarecci, S.; Filetici, P. A novel histone acetyltransferase inhibitor modulating Gcn5 network: cyclopentylidene-[4-(4′-chlorophenyl)thiazol-2- yl]hydrazone J. Med. Chem. 2009, 52 (2) 530-536