Development of fluorinated methoxylated chalcones as selective monoamine oxidase-B inhibitors: Synthesis, biochemistry and molecular docking studies

Bioorganic Chemistry

Volumn 62, Issue , 2015, Pages 22-29

  Mathew, Bijo ^a   Mathew, Githa Elizabeth ^b   Uçar, Gülberk ^c   Baysal, Ipek ^c   Suresh, Jerad ^d   Vilapurathu, Jobin Kunjumon ^a   Prakasan, Aneesh ^b   Suresh, Jeethu Kuruppath ^b   Thomas, Anjana ^b  

^a Division of Drug Design and Medicinal Chemistry Research Lab Department of Pharmaceutical Chemistry Grace College of Pharmacy   (India)

^b Grace College of Pharmacy   (India)

^c HACETTEPE UNIVERSITY   (Turkey)

^d MADRAS MEDICAL COLLEGE   (India)

Author keywords

MAO A; MAO B; Methoxylated chalcone; Molecular docking

Indexed keywords

1 (4 METHOXYPHENYL) 3 [2 (TRIFLUOROMETHYL) PHENYL] PROP 2 EN 1 ONE; 1 (4 METHOXYPHENYL) 3 [4 (TRIFLUOROMETHYL) PHENYL] PROP 2 EN 1 ONE; 3 (2 FLUOROPHENYL) 1 (4 METHOXYPHENYL) PROP 2 EN 1 ONE; 3 (3 FLUOROPHENYL) 1 (4 METHOXYPHENYL) PROP 2 EN 1 ONE; 3 (4 FLUOROPHENYL) 1 (4 METHOXYPHENYL) PROP 2 EN 1 ONE; CHALCONE DERIVATIVE; MONOAMINE OXIDASE B INHIBITOR; UNCLASSIFIED DRUG; 1-(4-METHOXYPHENYL)-3-(4-(TRIFLUOROMETHYL)PHENYL)PROP-2-EN-1-ONE; AMINE OXIDASE (FLAVIN CONTAINING); FLUORINATED HYDROCARBON; MONOAMINE OXIDASE A, HUMAN; MONOAMINE OXIDASE INHIBITOR; PROPANE;

ARTICLE; BIOCHEMISTRY; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG STRUCTURE; DRUG SYNTHESIS; FLUORESCENCE; IN VITRO STUDY; MOLECULAR DOCKING; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; ANALOGS AND DERIVATIVES; DRUG EFFECTS; HUMAN; SYNTHESIS;

CHALCONES; HUMANS; HYDROCARBONS, FLUORINATED; MOLECULAR DOCKING SIMULATION; MONOAMINE OXIDASE; MONOAMINE OXIDASE INHIBITORS; PROPANE;

EID: 84937955455     PISSN: 00452068     EISSN: 10902120     Source Type: Journal    
DOI: 10.1016/j.bioorg.2015.07.001     Document Type: Article

References (34)

1. M. Yáñez, J.F. Padín, J.A. Arranz-Tagarro, M. Camiña, and R. Laguna Curr. Top. Med. Chem. 12 2012 2275 2282
2. M.B.I. Youdim, and Y.S. Bakhle Br. J. Pharmacol. 147 2006 S287 S296
3. L. Oreland, S.S. Jossan, P. Hartvig, S.M. Aquilonius, and B. Langstrom J. Neural. Transm. Suppl. 32 1990 55 59
4. J. Reis, I. Encarnação, A. Gaspar, A. Morales, N. Milhazes, and F. Borges Curr. Top. Med. Chem. 12 2012 2177-2118
5. H.H. Fernandez, and J.J. Chen Pharmacotherapy 27 2007 174S 185S
6. G. Di Carlo, N. Mascolo, A.A. Izzo, and F. Capasso Life Sci. 65 1999 337 353
7. O. Afzal, S. Bawa, S. Kumar, R. Kumar, and Md.Q. Hassan Lett. Drug Des. Discov. 10 2013 75 85
8. S. Tanaka, Y. Kuwai, and M. Tabata Planta Med. 53 1987 5 8
9. T. Hatano, T. Fukuda, T. Miyase, T. Noro, and T. Okuda Chem. Pharm. Bull. 39 1991 1238 1243
10. X. Pan, L.D. Kong, Y. Zhang, C.H. Cheng, and R.X. Tan Acta Pharmacol. Sinica 21 2000 949 953
11. H. Haraguchi, Y. Tanaka, A. Kabbash, T. Fujioka, T. Ishizu, and A. Yagi Phytochemistry 65 2004 2255 2260
12. F. Chimenti, R. Fioravanti, A. Bolasco, P. Chimenti, D. Secci, F. Rossi, M. Yanez, F. Orallo, F. Ortuso, and S. Alcaro J. Med. Chem. 52 2009 2818 2824
13. G. Jo, S. Ahn, B.G. Kim, H.R. Park, Y.H. Kim, A.H. Cho, D. Koh, Y. Chong, J.H. Ahn, and Y. Lim Biorg. Med. Chem. 21 2013 7890 7897
14. S.J. Robinson, J.P. Petzer, A. Petzer, J.J. Bergh, and A.C.U. Lourens Bioorg. Med. Chem. Lett. 23 2013 4985 4989
15. B. Evranos-Aksöz, S. Yabanoʇlu-Çiftçi, G. Uçar, K. Yelekçi, and R. Ertan Bioorg. Med. Chem. Lett. 24 2014 3278 3284
16. 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 685 695
17. A.M. Helguera, G. Pérez-Machado, M.N.D.S. Cordeiro, and F. Borges Mini Rev. Med. Chem. 12 2012 907 919
18. B.V. Nayak, S. Ciftci-Yabanoglu, S. Bhakat, A.K. Timiri, B.N. Sinha, G. Ucar, M.E.S. Soliman, and V. Jayaprakash Bioorg. Chem. 58 2015 72 80
19. M.C. Anderson, F. Hasan, J.M. McCrodden, and K.F. Tipton Neurochem. Res. 18 1993 1145 1149
20. F. Chimenti, E. Maccioni, D. Secci, A. Bolasco, P. Chimenti, A. Granese, S. Carradori, S. Alcaro, F. Ortuso, and M. Yáñez J. Med. Chem. 51 2008 4874 4880
21. M. Yáñez, N. Fraiz, E. Cano, and F. Orallo Biochem. Biophys. Res. Commun. 344 2 2006 688 695
22. M.M. Bradford Anal. Biochem. 72 1976 248 254
23. F. Chimenti, S. Carradori, D. Secci, A. Bolasco, B. Bizzarri, P. Chimenti, A. Granese, M. Yáñez, and F. Orallo Eur. J. Med. Chem. 45 2010 800 804
24. G.M. Morris, R. Huey, W. Lindstrom, M.F. Sanner, R.K. Belew, D.S. Goodsell, and A.J. Olson J. Comput. Chem. 30 2009 2785 2791
25. L. De Colibus, M. Li, C. Binda, A. Lustig, D.E. Edmondson, and A. Mattevi Proc. Natl. Acad. Sci. USA 102 36 2005 12684 12689
26. B.V. Nayak, S. Ciftci-Yabanoglu, S.S. Jadav, M. Jagrat, B.N. Sinha, G. Ucar, and V. Jayaprakash Eur. J. Med. Chem. 69 2013 762 767
27. A.W. Schuttelkopf, and D.M. van Aalten Acta Crystallogr. D Biol. Crystallogr. 60 2004 1355 1363
28. B. Mathew, J. Suresh, and S. Anbazhagan S. Dev. Biomed. Aging Pathol. 4 2014 297 301
29. L.J. Legoabe, A. Petzer, and J.P. Petzer Chem. Biol. Drug Des. 2015 10.1111/cbdd.12508
30. C. Binda, M. Li, F. Hubalek, N. Restelli, and D.E. Edmondson Proc. Natl. Acad. Sci. USA 100 2003 9750 9755
31. L. Legoabe, J. Kruger, A. Petzer, J.J. Bergh, and J.P. Petzer Eur. J. Med. Chem. 46 2011 5162 5174
32. D.E. Edmondson, A. Mattevi, C. Binda, M. Li, and F. Hubalek Curr. Med. Chem. 11 2004 1983 1993
33. L. Novaroli, A. Daina, E. Favre, J. Bravo, A. Carotti, F. Leonetti, M. Catto, P.A. Carrupt, and M. Reist J. Med. Chem. 49 2006 6264 6272
34. B. Strydom, S.F. Malan Jr., N. Castagnoli, J.J. Bergh, and J.P. Petzer Bioorg. Med. Chem. 18 2010 1018 1028