Correction to: Discovery of New Chemical Entities for Old Targets: Insights on the Lead Optimization of Chromone-Based Monoamine Oxidase B (MAO-B) Inhibitors (Journal of Medicinal Chemistry (2016) 59 (5879-5893) DOI: 10.1021/acs.jmedchem.6b00527);Discovery of New Chemical Entities for Old Targets: Insights on the Lead Optimization of Chromone-Based Monoamine Oxidase B (MAO-B) Inhibitors

Journal of Medicinal Chemistry

Volumn 59, Issue 12, 2016, Pages 5879-5893

  Reis, Joana ^a   Cagide, Fernando ^a   Chavarria, Daniel ^a   Silva, Tiago ^a   Fernandes, Carlos ^a   Gaspar, Alexandra ^a   Uriarte, Eugenio ^b   Remião, Fernando ^a   Alcaro, Stefano ^c   Ortuso, Francesco ^c   Borges, Fernanda ^a  

^a UNIVERSITY OF PORTO   (Portugal)

^b UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^c UNIVERSITY MAGNA GRAECIA OF CATANZARO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME A; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME B; CARBONYL DERIVATIVE; CHROMONE DERIVATIVE; MONOAMINE OXIDASE B INHIBITOR; N (2' BROMOPHENYL) 4 OXO 4H CHROMENE 3 CARBOXAMIDE; N (2' CHLOROPHENYL) 4 OXO 4H CHROMENE 3 CARBOXAMIDE; N (2' HYDROXYPHENYL) 4 OXO 4H CHROMENE 3 CARBOXAMIDE; N (2',3' DIMETHYLPHENYL) 4 OXO 4H CHROMENE 3 CARBOXAMIDE; N (3' BROMOPHENYL) 4 OXO 4H CHROMENE 3 CARBOXAMIDE; N (3' CHLOROPHENYL) 4 OXO 4H CHROMENE 3 CARBOXAMIDE; N (3' HYDROXYPHENYL) 4 OXO 4H CHROMENE 3 CARBOXAMIDE; N (3',4' DICHLOROPHENYL) 4 OXO 4H CHROMENE 3 CARBOXAMIDE; N (3',4' DIMETHYLPHENYL) 4 OXO 4H CHROMENE 3 CARBOXAMIDE; N (3',4',5' TRICHLOROPHENYL) 4 OXO 4H CHROMENE 3 CARBOXAMIDE; N (3',4',5' TRIMETHYLPHENYL) 4 OXO 4H CHROMENE 3 CARBOXAMIDE; N (4' BROMOPHENYL) 4 OXO 4H CHROMENE 3 CARBOXAMIDE; N (4' ETHYLPHENYL) 4 OXO 4H CHROMENE 3 CARBOXAMIDE; N (4' ETHYNYLPHENYL) 4 OXO 4H CHROMENE 3 CARBOXAMIDE; N (4' FLUOROPHENYL) 4 OXO 4H CHROMENE 3 CARBOXAMIDE; N (4' IODOPHENYL) 4 OXO 4H CHROMENE 3 CARBOXAMIDE; N (4' MERCAPTOPHENYL) 4 OXO 4H CHROMENE 3 CARBOXAMIDE; N (4' VINYLPHENYL) 4 OXO 4H CHROMENE 3 CARBOXAMIDE; N (M TOLYL) 4 OXO 4H CHROMENE 3 CARBOXAMIDE; N (O TOLYL) 4 OXO 4H CHROMENE 3 CARBOXAMIDE; N METHYL N PHENYL 4 OXO 4H CHROMENE 3 CARBOXAMIDE; N [4' (DIMETHYLAMINO)PHENYL] 4 OXO 4H CHROMENE 3 CARBOXAMIDE; O (P TOLYL) 4 OXO 4H CHROMENE 3 CARBOXYLATE; TERT BUTYL [4 (4 OXO 4H CHROMENE 3 CARBOXAMIDE)PHENYL]CARBAMATE; UNCLASSIFIED DRUG; UNINDEXED DRUG; AMINE OXIDASE (FLAVIN CONTAINING); MONOAMINE OXIDASE INHIBITOR;

ARTICLE; BLOOD BRAIN BARRIER; CELL VIABILITY; CRYSTAL STRUCTURE; DRUG ABSORPTION; DRUG DISTRIBUTION; DRUG EXCRETION; DRUG METABOLISM; DRUG POTENCY; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC50; LIPOPHILICITY; MAXIMUM REACTION VELOCITY; MOLECULAR DOCKING; NEUROBLASTOMA CELL; STRUCTURE ACTIVITY RELATION; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG DEVELOPMENT; DRUG EFFECTS; METABOLISM; MOLECULAR MODEL; SYNTHESIS; TUMOR CELL CULTURE;

CELL SURVIVAL; CHROMONES; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DISCOVERY; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MONOAMINE OXIDASE; MONOAMINE OXIDASE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

EID: 84975871993     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/acs.jmedchem.8b00600     Document Type: Erratum

References (36)

1. Jankovic, J.; Aguilar, L. G. Current approaches to the treatment of Parkinson's disease Neuropsychiatr. Dis. Treat. 2008, 4, 743-757 10.2147/NDT.S2006
2. Schapira, A. H. V. Present and future drug treatment for Parkinson's disease J. Neurol., Neurosurg. Psychiatry 2005, 76, 1472-1478 10.1136/jnnp.2004.035980
3. Tipton, K. F.; Boyce, S.; O'Sullivan, J.; Davey, G. P.; Healy, J. Monoamine oxidases: certainties and uncertainties Curr. Med. Chem. 2004, 11, 1965-1982 10.2174/0929867043364810
4. Youdim, M. B.; Bakhle, Y. S. Monoamine oxidase: isoforms and inhibitors in Parkinson's disease and depressive illness Br. J. Pharmacol. 2006, 147 (Suppl. 1) S287-S296 10.1038/sj.bjp.0706464
5. Youdim, M. B. H. Why do we need multifunctional neuroprotective and neurorestorative drugs for Parkinson's and Alzheimer's diseases as disease modifying agents Exp. Neurobiol. 2010, 19, 1-14 10.5607/en.2010.19.1.1
6. De la Fuente-Fernández, R.; Sossi, V.; Huang, Z.; Furtado, S.; Lu, J.-Q.; Calne, D. B.; Ruth, T. J.; Stoessl, A. J. Levodopa-induced changes in synaptic dopamine levels increase with progression of Parkinson's disease: implications for dyskinesias Brain 2004, 127, 2747-2754 10.1093/brain/awh290
7. Youdim, M. B. H.; Gross, A.; Finberg, J. P. M. Rasagiline [N-propargyl-1R(+)-aminoindan], a selective and potent inhibitor of mitochondrial monoamine oxidase B Br. J. Pharmacol. 2001, 132, 500-506 10.1038/sj.bjp.0703826
8. Binda, C.; Wang, J.; Pisani, L.; Caccia, C.; Carotti, A.; Salvati, P.; Edmondson, D. E.; Mattevi, A. Structures of human monoamine oxidase B complexes with selective noncovalent inhibitors: safinamide and coumarin analogs J. Med. Chem. 2007, 50, 5848-5852 10.1021/jm070677y
9. Ellis, G. P. The Chemistry of Heterocyclic Compounds, Chromenes, Chromanones, and Chromones; Wiley: New York, 2009; Vol. 31, p 1085.
10. Gaspar, A.; Matos, M. J.; Garrido, J.; Uriarte, E.; Borges, F. Chromone: a valid scaffold in medicinal chemistry Chem. Rev. 2014, 114, 4960-4992 10.1021/cr400265z
11. Alcaro, S.; Gaspar, A.; Ortuso, F.; Milhazes, N.; Orallo, F.; Uriarte, E.; Yáñez, M.; Borges, F. Chromone-2- and -3-carboxylic acids inhibit differently monoamine oxidases A and B Bioorg. Med. Chem. Lett. 2010, 20, 2709-2712 10.1016/j.bmcl.2010.03.081
12. Gaspar, A.; Reis, J.; Fonseca, A.; Milhazes, N.; Viña, D.; Uriarte, E.; Borges, F. Chromone 3-phenylcarboxamides as potent and selective MAO-B inhibitors Bioorg. Med. Chem. Lett. 2011, 21, 707-709 10.1016/j.bmcl.2010.11.128
13. Gaspar, A.; Teixeira, F.; Uriarte, E.; Milhazes, N.; Melo, A.; Cordeiro, M. N. D. S.; Ortuso, F.; Alcaro, S.; Borges, F. Towards the discovery of a novel class of monoamine oxidase inhibitors: structure-property-activity and docking studies on chromone amides ChemMedChem 2011, 6, 628-632 10.1002/cmdc.201000452
14. Gaspar, A.; Silva, T.; Yáñez, M.; Vina, D.; Orallo, F.; Ortuso, F.; Uriarte, E.; Alcaro, S.; Borges, F. Chromone, a privileged scaffold for the development of monoamine oxidase inhibitors J. Med. Chem. 2011, 54, 5165-5173 10.1021/jm2004267
15. Cagide, F.; Silva, T.; Reis, J.; Gaspar, A.; Borges, F.; Gomes, L. R.; Low, J. N. Discovery of two new classes of potent monoamine oxidase-B inhibitors by tricky chemistry Chem. Commun. 2015, 51, 2832-2835 10.1039/C4CC08798D
16. Cagide, F.; Reis, J.; Gaspar, A.; Borges, F. Accelerating lead optimization of chromone carboxamide scaffold throughout microwave-assisted organic synthesis Tetrahedron Lett. 2011, 52, 6446-6449 10.1016/j.tetlet.2011.09.095
17. Vedachalam, S.; Zeng, J.; Gorityala, B. K.; Antonio, M.; Liu, X.-W. N-Heterocyclic carbene-catalyzed intramolecular aldehyde-nitrile cross coupling: an easy access to 3- aminochromones Org. Lett. 2010, 12, 352-355 10.1021/ol9026232
18. Abdel-Magid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures J. Org. Chem. 1996, 61, 3849-3862 10.1021/jo960057x
19. Joshi, R. S.; Mandhane, P. G.; Badadhe, P. V.; Gill, C. H. Development of practical methodologies for the synthesis of novel 3(4-oxo-4H-chromen-3-yl)acrylic acid hydrazides Ultrason. Sonochem. 2011, 18, 735-738 10.1016/j.ultsonch.2010.11.001
20. Gaspar, A.; Reis, J.; Matos, M. J.; Uriarte, E.; Borges, F. In search for new chemical entities as adenosine receptor ligands: development of agents based on benzo-γ-pyrone skeleton Eur. J. Med. Chem. 2012, 54, 914-918 10.1016/j.ejmech.2012.05.033
21. Leeson, P. D.; Springthorpe, B. The influence of drug-like concepts on decision-making in medicinal chemistry Nat. Rev. Drug Discovery 2007, 6, 881-890 10.1038/nrd2445
22. Clark, D. E. Rapid calculation of polar molecular surface area and its application to the prediction of transport phenomena. 2. Prediction of blood-brain barrier penetration J. Pharm. Sci. 1999, 88, 815-821 10.1021/js980402t
23. Barton, P.; Riley, R. J. A new paradigm for navigating compound property related drug attrition Drug Discovery Today 2016, 21, 72-81 10.1016/j.drudis.2015.09.010
24. Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings Adv. Drug Delivery Rev. 2001, 46, 3-26 10.1016/S0169-409X(00)00129-0
25. Hitchcock, S. A.; Pennington, L. D. Structure-brain exposure relationships J. Med. Chem. 2006, 49, 7559-7583 10.1021/jm060642i
26. Pajouhesh, H.; Lenz, G. R. Medicinal chemical properties of successful central nervous system drugs NeuroRx 2005, 2, 541-553 10.1602/neurorx.2.4.541
27. Baell, J. B.; Holloway, G. A. New substructure filters for removal of pan assay interference compounds (PAINS) from screening libraries and for their exclusion in bioassays J. Med. Chem. 2010, 53, 2719-2740 10.1021/jm901137j
28. Lobner, D. Comparison of the LDH and MTT assays for quantifying cell death: validity for neuronal apoptosis? J. Neurosci. Methods 2000, 96, 147-152 10.1016/S0165-0270(99)00193-4
29. Chimenti, F.; Bolasco, A.; Secci, D.; Chimenti, P.; Granese, A.; Carradori, S.; Yanez, M.; Orallo, F.; Ortuso, F.; Alcaro, S. Investigations on the 2-thiazolylhydrazyne scaffold: synthesis and molecular modeling of selective human monoamine oxidase inhibitors Bioorg. Med. Chem. 2010, 18, 5715-5723 10.1016/j.bmc.2010.06.007
30. Berman, H. M.; Westbrook, J.; Feng, Z.; Gilliland, G.; Bhat, T. N.; Weissig, H.; Shindyalov, I. N.; Bourne, P. E. The Protein Data Bank Nucleic Acids Res. 2000, 28, 235-242 10.1093/nar/28.1.235
31. Son, S. Y.; Ma, J.; Kondou, Y.; Yoshimura, M.; Yamashita, E.; Tsukihara, T. Structure of human monoamine oxidase A at 2.2-A resolution: the control of opening the entry for substrates/inhibitors Proc. Natl. Acad. Sci. U. S. A. 2008, 105, 5739-5744 10.1073/pnas.0710626105
32. MacroModel, version 10.8; Schrödinger, LLC: New York, NY, 2015.
33. Maestro, version 10.2; Schrödinger, LLC: New York, NY, 2015.
34. Glide, version 6.7; Schrödinger, LLC: New York, NY, 2015.
35. Impact, version 6.7; Schrödinger, LLC: New York, NY, 2015.
36. Desmond Molecular Dynamics System, version 4.2; D. E. Shaw Research: New York, NY, 2015.