Synthesis of a series of unsaturated ketone derivatives as selective and reversible monoamine oxidase inhibitors

Bioorganic and Medicinal Chemistry

Volumn 23, Issue 19, 2015, Pages 6486-6496

  Choi, Ji Won ^a,b   Jang, Bo Ko ^a,c   Cho, Nam Chul ^a   Park, Jong Hyun ^a   Yeon, Seul Ki ^a   Ju, Eun Ji ^a   Lee, Yong Sup ^c   Han, Gyoonhee ^b   Pae, Ae Nim ^a,d   Kim, Dong Jin ^a   Park, Ki Duk ^a,d  

^a Korea Institute of Science and Technology   (South Korea)

^b Yonsei University   (South Korea)

^c Kyung Hee University   (South Korea)

^d University of Science and Technology (UST)   (South Korea)

Author keywords

Chalcone; MAO B inhibitor; Monoamine oxidase; Reversible inhibitor; , Unsaturated carbonyl derivatives

Indexed keywords

1 (2 METHOXYPHENYL) 3 PHENYLPROP 2 EN 1 ONE; 1 (2 METHOXYPHENYL) 3 [2 (TRIFLUOROMETHYL)PHENYL]PROP 2 EN 1 ONE; 1 (3 METHOXYPHENYL) 3 PHENYLPROP 2 EN 1 ONE; 1 (3 METHOXYPHENYL) 3 [2 (TRIFLUOROMETHYL)PHENYL]PROP 2 EN 1 ONE; 1 (4 HYDROXYPHENYL) 3 (2 METHOXYPHENYL)PROP 2 EN 1 ONE; 1 (4 HYDROXYPHENYL) 3 PHENYLPROP 2 EN 1 ONE; 1 (4 HYDROXYPHENYL) 3 [2 (TRIFLUOROMETHYL)PHENYL]PROP 2 EN 1 ONE; 1 (4 METHOXYPHENYL) 3 (2 CHLOROPHENYL)PROP 2 EN 1 ONE; 1 (4 METHOXYPHENYL) 3 (2 FLUOROPHENYL)PROP 2 EN 1 ONE; 1 (4 METHOXYPHENYL) 3 (2 METHOXYPHENYL)PROP 2 EN 1 ONE; 1 (4 METHOXYPHENYL) 3 (3 METHOXYPHENYL)PROP 2 EN 1 ONE; 1 (4 METHOXYPHENYL) 3 (4 METHOXYPHENYL) PROP 2 EN 1 ONE; 1 (4 METHOXYPHENYL) 3 PHENYLPROP 2 EN 1 ONE; 1 (4 METHOXYPHENYL) 3 [2 (TRIFLUOROMETHYL)PHENYL]PROP 2 EN 1 ONE; 1 (4 METHOXYPHENYL) 3 [3 (TRIFLUOROMETHYL)PHENYL]PROP 2 EN 1 ONE; 1 (4 METHOXYPHENYL) 3 [4 (TRIFLUOROMETHYL)PHENYL]PROP 2 EN 1 ONE; 3 (2 CHLOROPHENYL) N (3 HYDROXYPHENYL) 2 PROPENAMIDE; 3 (2 CHLOROPHENYL) N (4 HYDROXYPHENYL) 2 PROPENAMIDE; 3 (2 CHLOROPHENYL) N (4 METHOXYPHENYL) 2 PROPENAMIDE; 3 (2 CHLOROPHENYL) N PHENYL 2 PROPENAMIDE; 3 [2 (TRIFLUOROMETHYL)PHENYL] N (3 FLUOROPHENYL) 2 PROPENAMIDE; 3 [2 (TRIFLUOROMETHYL)PHENYL] N (3 HYDROXYPHENYL) 2 PROPENAMIDE; 3 [2 (TRIFLUOROMETHYL)PHENYL] N (4 HYDROXYPHENYL) 2 PROPENAMIDE; 3 [2 (TRIFLUOROMETHYL)PHENYL] N (4 METHOXYPHENYL) 2 PROPENAMIDE; 3 [2 (TRIFLUOROMETHYL)PHENYL] N PHENYL 2 PROPENAMIDE; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME B; KETONE DERIVATIVE; MONOAMINE OXIDASE INHIBITOR; SELEGILINE; UNCLASSIFIED DRUG; UNINDEXED DRUG; AMINE OXIDASE (FLAVIN CONTAINING); HYDROGEN PEROXIDE; KETONE; PROTEIN BINDING; SCAVENGER;

ARTICLE; CONTROLLED STUDY; DRUG PROTEIN BINDING; DRUG SELECTIVITY; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HYDROPHOBICITY; IC50; MOLECULAR DOCKING; STRUCTURE ACTIVITY RELATION; BINDING SITE; CHEMISTRY; KINETICS; METABOLISM; PROTEIN TERTIARY STRUCTURE; SYNTHESIS;

BINDING SITES; FREE RADICAL SCAVENGERS; HUMANS; HYDROGEN PEROXIDE; KETONES; KINETICS; MOLECULAR DOCKING SIMULATION; MONOAMINE OXIDASE; MONOAMINE OXIDASE INHIBITORS; PROTEIN BINDING; PROTEIN STRUCTURE, TERTIARY; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84942197132     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2015.08.012     Document Type: Article

References (30)

1. A.S. Kalgutkar, D.K. Dalvie, N. Castagnoli, and T.J. Taylor Chem. Res. Toxicol. 14 2001 1139
2. R.B. Silverman Acc. Chem. Res. 28 1995 335
3. J.C. Shih, K. Chen, and M.J. Ridd Annu. Rev. Neurosci. 22 1999 197
4. M.B. Youdim, and J.P. Finberg Biochem. Pharmacol. 41 1991 155
5. J. Gottowik, A.M. Cesura, P. Malherbe, G. Lang, and M. Daprada FEBS Lett. 317 1993 152
6. R.M. Geha, I. Rebrin, K. Chen, and J.C. Shih J. Biol. Chem. 276 2001 9877
7. M.B. Youdim, D. Edmondson, and K.F. Tipton Nat. Rev. Neurosci. 7 2006 295
8. N.T. Tzvetkov, S. Hinz, P. Kuppers, M. Gastreich, and C.E. Muller J. Med. Chem. 57 2014 6679
9. J.P. Finberg Pharmacol. Ther. 143 2014 133
10. S. Duty, and P. Jenner Br. J. Pharmacol. 164 2011 1357
11. A. Lees Drugs Aging 22 2005 731
12. F. Hubalek, C. Binda, M. Li, Y. Herzig, J. Sterling, M.B. Youdim, A. Mattevi, and D.E. Edmondson J. Med. Chem. 47 2004 1760
13. S. Jo, O. Yarishkin, Y.J. Hwang, Y.E. Chun, M. Park, D.H. Woo, J.Y. Bae, T. Kim, J. Lee, H. Chun, H.J. Park, D.Y. Lee, J. Hong, H.Y. Kim, S.J. Oh, S.J. Park, H. Lee, B.E. Yoon, Y. Kim, Y. Jeong, I. Shim, Y.C. Bae, J. Cho, N.W. Kowall, H. Ryu, E. Hwang, D. Kim, and C. Lee J. Nat. Med. 20 2014 886
14. S. Carradori, and J.P. Petzer Expert Opin. Ther. Patents 25 2015 91
15. F. Chimenti, R. Fioravanti, A. Bolasco, P. Chimenti, D. Secci, F. Rossi, M. Yáñez, F. Orallo, F. Ortuso, and S. Alcaro J. Med. Chem. 52 2009 2818
16. S.J. Robinson, J.P. Petzer, A. Petzer, J.J. Bergh, and A.C.U. Lourens Bioorg. Med. Chem. Lett. 23 2013 4985
17. S.K. Kumar, E. Hager, C. Pettit, H. Gurulingappa, N.E. Davidson, and S.R. Khan J. Med. Chem. 46 2003 2813
18. M.L. Go, X. Wu, and X.L. Liu Curr. Med. Chem. 12 2005 483
19. J.R. Dimmock, D.W. Elias, M.A. Beazely, and N.M. Kandepu Curr. Med. Chem. 6 1999 1125
20. N. Morales-Camilo, C.O. Salas, C. Sanhueza, C. Espinosa-Bustos, S. Sepúlveda-Boza, M. Reyes-Parada, F. Gonzalez-Nilo, M. Caroli-Rezende, and A. Fierro Chem. Biol. Drug Des. 85 2015 685
21. S.Y. Woo, J.H. Kim, M.K. Moon, S.H. Han, S.K. Yeon, J.W. Choi, B.K. Jang, H.J. Song, Y.G. Kang, J.W. Kim, J. Lee, D.J. Kim, O. Hwang, and K.D. Park J. Med. Chem. 57 2014 1473
22. K.D. Park, P. Morieux, C. Salome, S.W. Cotten, O. Reamtong, C. Eyers, S.J. Gaskell, J.P. Stables, R.H. Liu, and H. Kohn J. Med. Chem. 52 2009 6897
23. V. Kumar, S. Kumar, M. Hassan, H. Wu, R.K. Thimmulappa, A. Kumar, S.K. Sharma, V.S. Parmar, S. Biswal, and S.V. Malhotra J. Med. Chem. 54 2011 4147
24. Y. Tsugeno, and A. Ito J. Biol. Chem. 272 1997 14033
25. E.M. Milczek, C. Binda, S. Rovida, A. Mattevi, and D.E. Edmondson FEBS J. 278 2011 4860
26. N. Desideri, A. Bolasco, R. Fioravanti, L.P. Monaco, F. Orallo, M. Yáñez, F. Ortuso, and S. Acaro J. Med. Chem. 54 2011 2155
27. L.H.A. Prins, J.P. Petzer, and S.F. Malan Eur. J. Med. Chem. 45 2010 4458
28. A. Detsi, M. Majdalani, C.A. Kontogiorgis, D. Hadjipavlou-Litina, and P. Kefalas Bioorg. Med. Chem. 17 2009 8073
29. M. Kunishima, C. Kawachi, J. Monta, K. Terao, F. Iwasaki, and S. Tani Tetrahedron 55 1999 13159
30. L.C. Seaver, and J.A. Imlay J. Bacteriol. 183 2001 7173