Combining QSAR classification models for predictive modeling of human monoamine oxidase inhibitors

European Journal of Medicinal Chemistry

Volumn 59, Issue , 2013, Pages 75-90

  Helguera, Aliuska Morales ^a,b   Pérez Garrido, Alfonso ^c   Gaspar, Alexandra ^a   Reis, Joana ^a   Cagide, Fernando ^a   Vina, Dolores ^d   Cordeiro, M Natália D S ^a   Borges, Fernanda ^a  

^a UNIVERSITY OF PORTO   (Portugal)

^b CENTRAL UNIVERSITY OF LAS VILLAS   (Cuba)

^c CATHOLIC UNIVERSITY OF MURCIA   (Spain)

^d UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

Consensus; hMAO A; hMAO B; Monoamine oxidase inhibitor; QSAR; Selectivity

Indexed keywords

2 HYDROXYMETHYL 4 OXO 4H BENZOPYRAN; 3 HYDROXYMETHYL 4 OXO 4H BENZOPYRAN; CHALCONE DERIVATIVE; CHROMONE DERIVATIVE; COUMARIN DERIVATIVE; ETHYL (6 CLORO 4 OXO 4H BENZOPYRAN) 2 CARBOXYLATE; ETHYL 4 OXO 4H BENZOPYRAN 2 CARBOXYLATE; ETHYL 4 OXO 4H BENZOPYRAN 3 CARBOXYLATE; HYDRAZONE DERIVATIVE; ISOENZYME; MONOAMINE OXIDASE INHIBITOR; PROPYL 4 OXO 4H BENZOPYRAN 2 CARBOXYLATE; PROPYL 4 OXO 4H BENZOPYRAN 3 CARBOXYLATE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CLASSIFICATION ALGORITHM; COLUMN CHROMATOGRAPHY; CONSENSUS; DISCRIMINANT ANALYSIS; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; MOLECULAR MODEL; PREDICTION; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RANDOMIZATION; STRUCTURE ANALYSIS;

CELL LINE, TUMOR; CELL PROLIFERATION; DRUG DESIGN; HUMANS; INHIBITORY CONCENTRATION 50; MODELS, BIOLOGICAL; MOLECULAR STRUCTURE; MONOAMINE OXIDASE INHIBITORS; OLIGOPEPTIDES; PRODRUGS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84870213017     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.10.035     Document Type: Article

References (92)

1. L.W. Elmer, and J.M. Bertoni The increasing role of monoamine oxidase type B inhibitors in Parkinson's disease therapy Expert Opin. Pharmacother. 9 2008 2759 2772
2. J.J. Chen, D.M. Swope, and K. Dashtipour Comprehensive review of rasagiline, a second-generation monoamine oxidase inhibitor, for the treatment of Parkinson's disease Clin. Ther. 29 2007 1825 1849
3. M.B. Youdim, D. Edmondson, and K.F. Tipton The therapeutic potential of monoamine oxidase inhibitors Nat. Rev. Neurosci. 7 2006 295 309
4. D.S. Knudsen Gerber Selegiline and rasagiline: twins or distant cousins? guidelines Consult Pharm. 26 2011 48 51
5. J.J. Chen, and D.M. Swope Pharmacotherapy for Parkinson's disease Pharmacotherapy 27 2007 161S 173S
6. J.K. Mallajosyula, D. Kaur, S.J. Chinta, S. Rajagopalan, A. Rane, D.G. Nicholls, D.A. Di Monte, H. Macarthur, and J.K. Andersen MAO B elevation in mouse brain astrocytes results in Parkinson's pathology PloS One 3 2008 e1616
7. J.S. Fowler, J. Logan, N.D. Volkow, G.J. Wang, R.R. MacGregor, and Y.S. Ding Monoamine oxidase: radiotracer development and human studies Methods 27 2002 263 277
8. C.M. Vandenberg MAOIs and transdermal delivery J. Clin. Psychiatry 73 2012 e28
9. A.A. Patkar, C.U. Pae, and P.S. Masand Transdermal selegiline: the new generation of monoamine oxidase inhibitors CNS Spectrum. 11 2006 363 375
10. O. Weinreb, T. Amit, O. Bar-Am, M. Yogev-Falach, and M.B. Youdim The neuroprotective mechanism of action of the multimodal drug ladostigil Front. Biosci. J. Virtual Libr. 13 2008 5131 5137
11. M.B. Núñez, F.P. Maguna, N.B. Okulika, and E.A. Castro QSAR modeling of the MAO inhibitory activity of xanthones derivatives Bioorg. Med. Chem. Lett. 14 2004 5611 5617
12. L. Pisani, G. Muncipinto, T. Miscioscia, i.O. Nicolott, F. Leonetti, M. Catto, C. Caccia, P. Salvati, R. Soto-Otero, E. Mendez-Alvarez, C. Passeleu, and A. Carotti Discovery of a novel class of potent coumarin monoamine oxidase B inhibitors: development and biopharmacological profiling of 7-[(3-chlorobenzyl) oxy]-4-[(methylamino)methyl]-2H-chromen-2-one methanesulfonate (NW-1772) as a highly potent, selective, reversible, and orally active monoamine oxidase B inhibitor J. Med. Chem. 52 21 2009 6685 6706
13. M.J. Matos, D. Vina, C. Picciau, F. Orallo, L. Santana, and E. Uriarte Synthesis and evaluation of 6-methyl-3-phenylcoumarins as potent and selective MAO-B inhibitors Bioorg. Med. Chem. Lett. 19 2009 5053 5055
14. M.J. Matos, D. Viña, E. Quezada, C. Picciau, G. Delogu, F. Orallo, L. Santana, and E. Uriarte A new series of 3-phenylcoumarins as potent and selective MAO-B inhibitors Bioorg. Med. Chem. Lett. 19 2009 3268 3270
15. N. Gökhan-Kelekçi, O. Simşek, A. Ercan, K. Yelekçi, Z. Sahin, S. Işik, G. Uçar, and A. Bilgin Synthesis and molecular modeling of some novel hexahydroindazole derivatives as potent monoamine oxidase inhibitors Bioorg. Med. Chem. 17 18 2009 6761 6772
16. L.H. Prins, J.P. Petzer, and S.F. Malan Inhibition of monoamine oxidase by indole and benzofuran derivatives Eur. J. Med. Chem. 45 2010 4458 4466
17. R. Fioravanti, A. Bolasco, F. Manna, F. Rossi, F. Orallo, M. Yáñez, A. Vitali, F. Ortuso, and S. Alcaro Synthesis and molecular modelling studies of prenylated pyrazolines as MAO-B inhibitors Bioorg. Med. Chem. Lett. 20 2010 6479 6482
18. J. Wouters, F. Ooms, S. Jegham, J.J. Koenig, P. George, and F. Durant Reversible inhibition of type B monoamine oxidase. Theoretical study of model diazo heterocyclic compounds Eur. J. Med. Chem. 32 1997 721 730
19. S. Kneubühler, U. Thull, C. Altomare, V. Carta, P. Gaillard, P.A. Carrupt, A. Carotti, and B. Testa Inhibition of monoamine oxidase-b by 5H-Indeno[1,2c]pyridazines: biological activities, quantitative structure-activity relationships (QSARs) and 3D-QSARS J. Med. Chem. 1995 3874 3883
20. S. Alcaro, A. Gaspar, F. Ortuso, N. Milhazes, F. Orallo, E. Uriarte, M. Yáñez, and F. Borges Chromone-2- and -3-carboxylic acids inhibit differently monoamine oxidases A and B Bioorg. Med. Chem. Lett. 20 2010 2709 2712
21. A. Gaspar, J. Reis, A. Fonseca, N. Milhazes, D. Vina, E. Uriarte, and F. Borges Chromone 3-phenylcarboxamides as potent and selective MAO-B inhibitors Bioorg. Med. Chem. Lett. 21 2011 707 709
22. A. Gaspar, F. Teixeira, E. Uriarte, N. Milhazes, A. Melo, N.D.S. Cordeiro, F. Ortuso, S. Alcaro, and F. Borges Towards the discovery of a novel class of monoamine oxidase inhibitors: structure-property-activity and docking studies on chromone amides ChemMedChem 6 2011 628 632
23. A. Gaspar, T. Silva, M. Yáñez, D. Vina, F. Orallo, F. Ortuso, E. Uriarte, S. Alcaro, and F. Borges Chromone a privileged scaffold for the development of monoamine oxidase inhibitors J. Med. Chem. 54 2011 5165 5173
24. F. Chimenti, A. Bolasco, F. Manna, D. Secci, P. Chimenti, A. Granese, O. Befani, P. Turini, R. Cirilli, F. La Torre, S. Alcaro, F. Ortuso, and T. Langer Synthesis, biological evaluation and 3D-QSAR of 1,3,5-Trisubstituted-4,5- Dihydro-(1H)-pyrazole derivatives as potent and highly selective monoamine oxidase a inhibitors Curr. Med. Chem. 13 2006 1411 1428
25. A. Helguera, R. Combes, M. González, and N. Cordeiro Applications of 2D descriptors in drug design: a DRAGON tale Curr. Top. Med. Chem. 8 2008 1628 1655
26. A.E. Medvedev, A.V. Veselovsky, V.I. Shvedov, O.V. Tikhonova, T.A. Moskvitina, O.A. Fedotova, L.N. Axenova, N.S. Kamyshanskaya, A.Z. Kirkel, and A.S. Ivanov Inhibition of monoamine oxidase by pirlindole analogues: 3D-QSAR and CoMFA analysis J. Chem. Inf. Comput. Sci. 38 1998 1137 1144
27. C. Gnerre, M. Catto, F. Leonetti, P. Weber, P.A. Carrupt, C. Altomare, A. Carotti, and B. Testa Inhibition of monoamine oxidases by functionalized coumarin derivatives: biological activities, QSARs, and 3D-QSARs J. Med. Chem. 43 2000 4747 4758
28. L. Santana, H. González-Díaz, E. Quezada, E. Uriarte, M. Yáñez, D. Viña, and F. Orallo Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors J. Med. Chem. 51 2008 6740 6751
29. Y.C. Martin, J.B. Holland, C.H. Jarboe, and N. Plotnikoff Discriminant analysis of the relationship between physical properties and the inhibition of monoamine oxidase by aminotetralins and aminoindans J. Med. Chem. 17 1974 409 413
30. A. Gallardo-Godoy, A. Fierro, T.H. McLean, M. Castillo, B.K. Cassels, M. Reyes-Parada, and D.E. Nichols Sulfur-substituted r-alkyl phenethylamines as selective and reversible MAO-a inhibitors: biological activities, CoMFA analysis, and active site modeling J. Med. Chem. 48 2005 2407 2419
31. W.T. Harkcom, and D.R. Bevan Molecular docking of inhibitors into monoamine oxidase B Biochem. Biophys. Res. Commun. 360 2007 401 406
32. F. Chimenti, D. Secci, A. Bolasco, P. Chimenti, A. Granese, S. Carradori, E. Maccioni, M.C. Cardia, M. Yáñez, F. Orallo, S. Alcaro, F. Ortuso, R. Cirilli, R. Ferretti, S. Distinto, J. Kirchmair, and T. Langer Synthesis, semipreparative HPLC separation, biological evaluation, and 3D-QSAR of hydrazothiazole derivatives as human monoamine oxidase B inhibitors Bioorg. Med. Chem. 18 2010 5063 5070
33. M. Reyes-Parada, A. Fierro, P. Iturriaga-Vásquez, and B.K. Cassels Monoamine oxidase inhibition in the light of new structural data Curr. Enzym. Inhib. 1 2005 85 95
34. J. Bajorath Methods in molecular biology J.M. Walker, Chemoinformatics: Concepts, Methods, and Tools for Drug Discovery 2004 Humana Press Inc. Totowa, New Jersey
35. C. Lemmen, and T. Lengauer Computational methods for the structural alignment of molecules J. Comput. Aided Mol. Des. 14 2000 215 232
36. C. Binda, M. Li, F. Hubalek, N. Restelli, D.E. Edmondson, and A. Mattevi Insights into the mode of inhibition of human mitochondrial monoamine oxidase B from high-resolution crystal structures Proc. Natl. Acad. Sci. U. S. A. 100 2003 9750 9755
37. S.Y. Son, J. Ma, Y. Kondou, M. Yoshimura, E. Yamashita, and T. Tsukihara 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. 105 2008 5739 5744
38. A. Tropsha, P. Gramatica, and V.K. Gombar The importance of being earnest: validation is the absolute essential for successful application and interpretation of QSPR models QSAR Comb. Sci. 22 2003 69 77
39. J.A. Moron, M. Campillo, V. Pérez, M. Unzeta, and L.J. Pardo Molecular determinants of MAO selectivity in a series of indolylmethylamine derivatives: biological activities, 3D-QSAR/CoMFA analysis, and computational simulation of ligand recognition J. Med. Chem. 43 2000 1684 1691
40. M. Li, F. Hubalek, P. Newton-Vinson, and D.E. Edmondson Highlevel expression of human liver monoamine oxidase A in Pichia pastoris: comparison with the enzyme expressed in Saccharomyces cerevisiae Protein Expr. Purif. 24 2002 152 162
41. P. Newton-Vinson, F. Hubalek, and D.E. Edmondson High-level expression of human liver monoamine oxidase B in Pichia pastoris Protein Expr. Purif. 20 2000 334 345
42. C. Binda, F. Hubalek, M. Li, Y. Herzig, J. Sterling, D.E. Edmondson, and A. Mattevi Crystal structures of MAO B in complex with four inhibitors of the N-propargylaminoindan class J. Med. Chem. 47 2004 1767 1774
43. F. Chimenti, R. Fioravanti, A. Bolasco, P. Chimenti, D. Secci, F. Rossi, M. Yáñez, F. Orallo, F. Ortuso, and S. Alcaro Chalcones: a valid scaffold for monoamine oxidases inhibitors J. Med. Chem. 52 2009 2818 2824
44. F. Chimenti, D. Secci, A. Bolasco, P. Chimenti, B. Bizzarri, A. Granese, S. Carradori, M. Yáñez, F. Orallo, F. Ortuso, and S. Alcaro Synthesis, molecular modeling, and selective inhibitory activity against human monoamine oxidases of 3-carboxamido-7-substituted coumarins J. Med. Chem. 52 2009 1935 1942
45. F. Chimenti, S. Carradori, D. Secci, A. Bolasco, P. Chimenti, A. Granese, and B. Bizzarri Synthesis and biological evaluation of novel conjugated coumarin-thiazole systems J. Heterocycl. Chem. 46 2009 575 578
46. F. Chimenti, D. Secci, A. Bolasco, P. Chimenti, A. Granese, S. Carradori, M. Yáñez, F. Orallo, M.L. Sanna, B. Gallinella, and R. Cirilli Synthesis, stereochemical separation, and biological evaluation of selective inhibitors of human MAO-B: 1-(4-arylthiazol-2-yl)-2-(3-methylcyclohexylidene) hydrazines J. Med. Chem. 53 2010 6516 6520
47. F. Chimenti, D. Secci, A. Bolasco, P. Chimenti, A. Granese, S. Carradori, M. D'Ascenzio, M. Yáñez, and F. Orallo Synthesis and selective inhibition of human monoamine oxidases of a large scaffold of (4,5-substituted-thiazol-2-yl)hydrazones Med. Chem. Commun. 1 2010 61 72
48. N. Desideri, A. Bolasco, R. Fioravanti, L.P. Monaco, F. Orallo, M. Yáñez, F. Ortuso, and S. Alcaro Homoisoflavonoids: natural scaffolds with potent and selective monoamine oxidase-B inhibition properties J. Med. Chem. 54 2011 2155 2164
49. E. Maccioni, S. Alcaro, F. Orallo, M.C. Cardia, S. Distinto, G. Costa, M. Yáñez, M.L. Sanna, S. Vigo, R. Meleddu, and D. Secci Synthesis of new 3-aryl-4,5-dihydropyrazole-1-carbothioamide derivatives. An investigation on their ability to inhibit monoamine oxidase Eur. J. Med. Chem. 45 2010 4490 4498
50. M.J. Matos, D. Vina, P. Janeiro, F. Borges, L. Santana, and E. Uriarte New halogenated 3-phenylcoumarins as potent and selective MAO-B inhibitors Bioorg. Med. Chem. Lett. 20 2010 5157 5160
51. F. Chimenti, A. Bolasco, D. Secci, P. Chimenti, A. Granese, S. Carradori, M. Yáñez, F. Orallo, F. Ortuso, and S. Alcaro Investigations on the 2-thiazolylhydrazyne scaffold: synthesis and molecular modeling of selective human monoamine oxidase inhibitors Bioorg. Med. Chem. 18 2010 5715 5723
52. F. Chimenti, S. Carradori, D. Secci, A. Bolasco, B. Bizzarri, P. Chimenti, A. Granese, M. Yáñez, and F. Orallo Synthesis and inhibitory activity against human monoamine oxidase of N1-thiocarbamoyl-3,5- di(hetero)aryl-4,5-dihydro-(1H)-pyrazole derivatives Eur. J. Med. Chem. 45 2010 800 804
53. F. Chimenti, R. Fioravanti, A. Bolasco, P. Chimenti, D. Secci, F. Rossi, M. Yáñez, F. Orallo, F. Ortuso, S. Alcaro, R. Cirilli, R. Ferretti, and M.L. Sanna A new series of flavones, thioflavones, and flavanones as selective monoamine oxidase-B inhibitors Bioorg. Med. Chem. 18 2010 1273 1279
54. N.E. Vergel, J.L. Lopez, F. Orallo, D. Vina, D.M. Buitrago, E. del Olmo, J.A. Mico, and M.F. Guerrero Antidepressant-like profile and MAO-A inhibitory activity of 4-propyl-2H-benzo[h]-chromen-2-one Life Sci. 86 2010 819 824
55. G. Delogu, C. Picciau, G. Ferino, E. Quezada, G. Podda, E. Uriarte, and D. Vina Synthesis, human monoamine oxidase inhibitory activity and molecular docking studies of 3-heteroarylcoumarin derivatives Eur. J. Med. Chem. 46 2011 1147 1152
56. L. Novaroli, A. Daina, E. Favre, J. Bravo, A. Carotti, F. Leonetti, M. Catto, P.A. Carrupt, and M. Reist Impact of species-dependent differences on screening, design, and development of MAO B inhibitors J. Med. Chem. 49 2006 6264 6272
57. M. Yáñez, N. Fraiz, E. Cano, and F. Orallo Inhibitory effects of cis- and trans-resveratrol on noradrenaline and 5-hydroxytryptamine uptake and on monoamine oxidase activity Biochem. Biophys. Res. Commun. 344 2006 688 695
58. M.J. Matos, C. Teran, Y. Perez-Castillo, E. Uriarte, L. Santana, and D. Vina Synthesis and study of a series of 3-arylcoumarins as potent and selective monoamine oxidase B inhibitors J. Med. Chem. 54 2011 7127 7137
59. I. StatSoft STATISTICA (Data Analysis Software System), Version 8.0 2007 USA www.statsoft.com
60. s. Talete Dragon for Windows (Software for Molecular Descriptors Calculation) version 5.4-2006 2006 Milano, Italy www.talete.mi.it
61. Molecular Operating Environment (MOE) 2008 Chemical Computing Group. Inc. Montreal, QC, Canada
62. Y. Gutierrez, and E. Estrada MODESLAB 1.0 (Molecular DEScriptors LABoratory) for Windows 2002
63. B.K. Sharma, P. Pilania, K. Sarbhai, P. Singh, and Y.S. Prabhakar Chemometric descriptors in modeling the carbonic anhydrase inhibition activity of sulfonamide and sulfamate derivatives Mol. Divers. 14 2010 371 384
64. M.Y. Shen, B.H. Su, E.X. Esposito, A.J. Hopfinger, and Y.J. Tseng A comprehensive support vector machine binary HERG classification model based on extensive but biased end point HERG data sets Chem. Res. Toxicol. 24 2011 934 949
65. E. Estrada How the parts organize in the whole? A top-down view of molecular descriptors and properties for QSAR and drug design Mini Rev. Med. Chem. 8 2008 213 221
66. R.A. Fisher The use of multiple measurements in taxonomic problems Ann. Eugen. 7 1936 179 188
67. A.M. Helguera, P.R. Duchowicz, M.Á.C. Pérez, E.A. Castro, M.N.D.S. Cordeiro, and M.P. González Application of the replacement method as a novel variable selection strategy in QSAR. 1. Carcinogenic potential Chemom. Intell. Lab. Syst. 81 2006 180
68. A. Perez-Garrido, A.M. Helguera, F. Borges, M.N. Cordeiro, V. Rivero, and A.G. Escudero Two new parameters based on distances in a receiver operating characteristic chart for the selection of classification models J. Chem. Inf. Model. 51 2011 2746 2759
69. R. Leardi Nature-inspired Methods in Chemometrics: Genetic Algorithms and Artificial Neural Networks 2003 Elsevier Genova, Italy
70. H. Kubinyi Variable selection in QSAR studies. I. An evolutionary algorithm Quant. Struct. Activity Relatsh. 13 1994 285 294
71. F. Provost, and T. Fawcett Analysis and Visualization of Classifier Performance: Comparison under Imprecise Class and Cost Distributions 1997 AAAI Press Huntington Beach, CA, Menlo Park
72. D.A. Pearlman, and P.S. Charifson Improved scoring of ligand-protein interactions using OWFEG free energy grids J. Med. Chem. 44 2001 502 511
73. B.W. Matthews Comparison of the predicted and observed secondary structure of T4 phage lysozyme Biochim. Biophys. Acta 405 1975 442 451
74. R.P. Sheridan, S.B. Singh, E.M. Fluder, and S.K. Kearsley Protocols for bridging the peptide to nonpeptide gap in topological similarity searches J. Chem. Inf. Comput. Sci. 41 2001 1395 1406
75. J.F. Truchon, and C.I. Bayly Evaluating virtual screening methods: good and bad metrics for the "early recognition" problem J. Chem. Inf. Model. 47 2007 488 508
76. S. Wold, and L. Eriksson Statistical validation of QSAR results H. van de Waterbeemd, Chemometrics Methods in Molecular Design 1995 VCH New York 309 318
77. T.I. Netzeva, A.P. Worth, T. Aldenberg, R. Benigni, M.T.D. Cronin, P. Gramatica, J.S. Jaworska, S. Kahn, G. Klopman, C.A. Marchant, G. Myatt, N. Nikolova-Jeliazkova, G.Y. Patlewicz, R. Perkins, D.W. Roberts, T.W. Schultz, D.T. Stanton, J.J.M. van de Sandt, W. Tong, G. Veith, and C. Yang Current status of methods for defining the applicability domain of (quantitative) structure-activity relationships. The report and recommendations of ECVAM workshop 52 Altern. Lab. Anim. 33 2005 155 173
78. S. Zhang, A. Golbraikh, S. Oloff, H. Kohn, and A. Tropsha A novel automated lazy learning QSAR (ALL-QSAR) approach: method development, applications, and virtual screening of chemical databases using validated ALL-QSAR models J. Chem. Inf. Model. 46 2006 1984 1995
79. G. Melagraki, A. Afantitis, H. Sarimveis, P.A. Koutentis, G. Kollias, and O. Igglessi-Markopoulou Predictive QSAR workflow for the in silico identification and screening of novel HDAC inhibitors Mol. Divers. 13 2009 301 311
80. L. Eriksson, J. Jaworska, A.P. Worth, M.T.D. Cronin, R.M. McDowell, and P. Gramatica Methods for reliability and uncertainty assessment and for applicability evaluations of classification- and regression-based QSARs Environ. Health Perspect. 111 2003 1361 1375
81. L.I. Kuncheva Combining Pattern Classifiers. Methods and Algorithms 2004 John Wiley & Sons, Inc. Hoboken, New Jersey
82. G.P. Ellis, G.J. Becket, D. Shaw, H.K. Wilson, C.J. Vardey, and I.F. Skidmore Benzopyrones. 14. Synthesis and antiallergic properties of some N-tetrazolylcarboxamides and related compounds J. Med. Chem. 21 1978 1120 1126
83. D.N. Davidson, and P.T. Kaye Chromone studies. Part 3. NMR analysis of rotational isomerism in 4-oxo-4H-chromene-2-carboxamides J. Chem. Soc. Perkin Trans. 2 1991 927 930
84. A. Gaspar, E.M. Garrido, M. Esteves, E. Quezada, N. Milhazes, J. Garrido, and F. Borges New insights into the antioxidant activity of hydroxycinnamic acids: synthesis and physicochemical characterization of novel halogenated derivatives Eur. J. Med. Chem. 44 2009 2092 2099
85. M. Hadjeri, M. Barbier, X. Ronot, A.M. Mariotte, A. Boumendjel, and J. Boutonnat Modulation of P-glycoprotein-mediated multidrug resistance by flavonoid derivatives and analogues J. Med. Chem. 46 2003 2125 2131
86. N. Ishizuka, K. Matsumura, K. Sakai, M. Fujimoto, S. Mihara, and T. Yamamori Structure-activity relationships of a novel class of endothelin-A receptor antagonists and discovery of potent and selective receptor antagonist, 2-(benzo[1,3]dioxol-5-yl)-6-isopropyloxy-4-(4-methoxyphenyl)-2H-chromene-3- carbox ylic acid (S-1255). 1. Study on structure-activity relationships and basic structure crucial for ET(A) antagonism J. Med. Chem. 45 2002 2041 2055
87. T. Walenzyk, C. Carola, H. Buchholz, and B. König Chromone derivatives which bind to human hair Tetrahedron 61 2005 7366 7377
88. M. Payard, M. Geneviève, P. Tronche, P. Bastide, and J. Bastide Recherche de composés antiallergiques dérivés de ĺhydroxyméthyl-2 chromone et analogues structuraux Eur. J. Med. Chem. 20 1985 117 120
89. P.-L. Zhao, J. Li, and G.-F. Yang Synthesis and insecticidal activity of chromanone and chromone analogues of diacylhydrazines Bioorg. Med. Chem. 15 2007 1888 1895
90. R. Araya-Maturana, J. Heredia-Moya, H. Pessoa-Mahana, and B. Weiss-López Improved selective reduction of 3-formylchromones using basic alumina and 2-propanol Synth. Commun. 33 2003 3225 3231
91. R. Todeschini, V. Consonni, and M. Pavan A distance measure between models: a tool for similarity/diversity analysis of model populations Chemom. Intell. Lab. Syst. 70 2004 55 61
92. A.K. Upadhyay, and D.E. E. Development of spin-labeled pargyline analogues as specific inhibitors of human monoamine oxidases A and B Biochemistry 48 2009 3928 3935