Generic placeholder image

Mini-Reviews in Medicinal Chemistry

Editor-in-Chief

ISSN (Print): 1389-5575
ISSN (Online): 1875-5607

Mini-Review Article

Single Heterocyclic Compounds as Monoamine Oxidase Inhibitors: From Past to Present

Author(s): Su-Min Wu, Xiao-Yang Qiu*, Shu-Juan Liu and Juan Sun*

Volume 20, Issue 10, 2020

Page: [908 - 920] Pages: 13

DOI: 10.2174/1389557520666200302114620

Price: $65

Abstract

Inhibitors of monoamine oxidase (MAO) have shown therapeutic values in a variety of neurodegenerative diseases such as depression, Parkinson’s disease and Alzheimer’s disease. Heterocyclic compounds exhibit a broad spectrum of biological activities and vital leading compounds for the development of chemical drugs. Herein, we focus on the synthesis and screening of novel single heterocyclic derivatives with MAO inhibitory activities during the past decade. This review covers recent pharmacological advancements of single heterocyclic moiety along with structure- activity relationship to provide better correlation among different structures and their receptor interactions.

Keywords: Monoamine oxidase inhibitors, heterocyclic compounds, structure-activity relationship, bioactivities, H2O2, FAD.

Graphical Abstract

[1]
Edmondson, D.E.; Mattevi, A.; Binda, C.; Li, M.; Hubálek, F. Structure and mechanism of monoamine oxidase. Curr. Med. Chem., 2004, 11(15), 1983-1993.
[http://dx.doi.org/10.2174/0929867043364784] [PMID: 15279562]
[2]
Tipton, K.F. Enzymology of monoamine oxidase. Cell Biochem. Funct., 1986, 4(2), 79-87.
[http://dx.doi.org/10.1002/cbf.290040202] [PMID: 3518979]
[3]
Kalgutkar, A.S.; Dalvie, D.K.; Castagnoli, N., Jr; Taylor, T.J. Interactions of nitrogen-containing xenobiotics with monoamine oxidase (MAO) isozymes A and B: SAR studies on MAO substrates and inhibitors. Chem. Res. Toxicol., 2001, 14(9), 1139-1162.
[http://dx.doi.org/10.1021/tx010073b] [PMID: 11559028]
[4]
Youdim, M.B.H.; Finberg, J.P.M. New directions in monoamine oxidase A and B selective inhibitors and substrates. Biochem. Pharmacol., 1991, 41(2), 155-162.
[http://dx.doi.org/10.1016/0006-2952(91)90471-G] [PMID: 1989626]
[5]
Gottowik, J.; Cesura, A.M.; Malherbe, P.; Lang, G.; Da Prada, M. Characterisation of wild-type and mutant forms of human monoamine oxidase A and B expressed in a mammalian cell line. FEBS Lett., 1993, 317(1-2), 152-156.
[http://dx.doi.org/10.1016/0014-5793(93)81512-X] [PMID: 8428624]
[6]
Geha, R.M.; Rebrin, I.; Chen, K.; Shih, J.C. Substrate and inhibitor specificities for human monoamine oxidase A and B are influenced by a single amino acid. J. Biol. Chem., 2001, 276(13), 9877-9882.
[http://dx.doi.org/10.1074/jbc.M006972200] [PMID: 11134050]
[7]
Westlund, K.N.; Denney, R.M.; Kochersperger, L.M.; Rose, R.M.; Abell, C.W. Distinct monoamine oxidase A and B populations in primate brain. Science, 1985, 230(4722), 181-183.
[http://dx.doi.org/10.1126/science.3875898] [PMID: 3875898]
[8]
Bach, A.W.J.; Lan, N.C.; Johnson, D.L.; Abell, C.W.; Bembenek, M.E.; Kwan, S.W.; Seeburg, P.H.; Shih, J.C. cDNA cloning of human liver monoamine oxidase A and B: molecular basis of differences in enzymatic properties. Proc. Natl. Acad. Sci. USA, 1988, 85(13), 4934-4938.
[http://dx.doi.org/10.1073/pnas.85.13.4934] [PMID: 3387449]
[9]
Grimsby, J.; Chen, K.; Wang, L.J.; Lan, N.C.; Shih, J.C. Human monoamine oxidase A and B genes exhibit identical exon-intron organization. Proc. Natl. Acad. Sci. USA, 1991, 88(9), 3637-3641.
[http://dx.doi.org/10.1073/pnas.88.9.3637] [PMID: 2023912]
[10]
Westlund, K.N.; Denney, R.M.; Rose, R.M.; Abell, C.W. Localization of distinct monoamine oxidase A and monoamine oxidase B cell populations in human brainstem. Neuroscience, 1988, 25(2), 439-456.
[http://dx.doi.org/10.1016/0306-4522(88)90250-3] [PMID: 3399053]
[11]
Saura, J.; Richards, J.G.; Mahy, N. Differential age-related changes of MAO-A and MAO-B in mouse brain and peripheral organs. Neurobiol. Aging, 1994, 15(4), 399-408.
[http://dx.doi.org/10.1016/0197-4580(94)90071-X] [PMID: 7969716]
[12]
Weyler, W.; Hsu, Y.P.; Breakefield, X.O. Biochemistry and genetics of monoamine oxidase. Pharmacol. Ther., 1990, 47(3), 391-417.
[http://dx.doi.org/10.1016/0163-7258(90)90064-9] [PMID: 2290855]
[13]
Youdim, M.B.H.; Edmondson, D.; Tipton, K.F. The therapeutic potential of monoamine oxidase inhibitors. Nat. Rev. Neurosci., 2006, 7(4), 295-309.
[http://dx.doi.org/10.1038/nrn1883] [PMID: 16552415]
[14]
Andrews, J.M.; Nemeroff, C.B. Contemporary management of depression. Am. J. Med., 1994, 97(6A), 24S-32S.
[http://dx.doi.org/10.1016/0002-9343(94)90360-3] [PMID: 7992823]
[15]
Carradori, S.; Secci, D.; Petzer, J.P. MAO inhibitors and their wider applications: a patent review. Expert Opin. Ther. Pat., 2018, 28(3), 211-226.
[http://dx.doi.org/10.1080/13543776.2018.1427735] [PMID: 29324067]
[16]
Yamada, M.; Yasuhara, H. Clinical pharmacology of MAO inhibitors: safety and future. Neurotoxicology, 2004, 25(1-2), 215-221.
[http://dx.doi.org/10.1016/S0161-813X(03)00097-4] [PMID: 14697896]
[17]
Rudorfer, M.V.; Potter, W.Z. Antidepressants. A comparative review of the clinical pharmacology and therapeutic use of the ‘newer’ versus the ‘older’ drugs. Drugs, 1989, 37(5), 713-738.
[http://dx.doi.org/10.2165/00003495-198937050-00006] [PMID: 2663417]
[18]
Pålhagen, S.; Heinonen, E.; Hägglund, J.; Kaugesaar, T.; Mäki-Ikola, O.; Palm, R. Swedish Parkinson Study Group. Selegiline slows the progression of the symptoms of Parkinson disease. Neurology, 2006, 66(8), 1200-1206.
[http://dx.doi.org/10.1212/01.wnl.0000204007.46190.54] [PMID: 16540603]
[19]
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.
[http://dx.doi.org/10.1016/j.amjopharm.2006.12.001] [PMID: 17296539]
[20]
Riederer, P.; Danielczyk, W.; Grünblatt, E. Monoamine oxidase-B inhibition in Alzheimer’s disease. Neurotoxicology, 2004, 25(1-2), 271-277.
[http://dx.doi.org/10.1016/S0161-813X(03)00106-2] [PMID: 14697902]
[21]
Youdim, M.B.H.; Fridkin, M.; Zheng, H. Novel bifunctional drugs targeting monoamine oxidase inhibition and iron chelation as an approach to neuroprotection in Parkinson’s disease and other neurodegenerative diseases. J. Neural Transm. (Vienna), 2004, 111(10-11), 1455-1471.
[http://dx.doi.org/10.1007/s00702-004-0143-x] [PMID: 15480846]
[22]
De Colibus, L.; Li, M.; Binda, C.; Lustig, A.; Edmondson, D.E.; Mattevi, A. Three-dimensional structure of human monoamine oxidase A (MAO A): relation to the structures of rat MAO A and human MAO B. Proc. Natl. Acad. Sci. USA, 2005, 102(36), 12684-12689.
[http://dx.doi.org/10.1073/pnas.0505975102] [PMID: 16129825]
[23]
Binda, C.; Newton-Vinson, P.; Hubálek, F.; Edmondson, D.E.; Mattevi, A. Structure of human monoamine oxidase B, a drug target for the treatment of neurological disorders. Nat. Struct. Biol., 2002, 9(1), 22-26.
[http://dx.doi.org/10.1038/nsb732] [PMID: 11753429]
[24]
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(7), 1767-1774.
[http://dx.doi.org/10.1021/jm031087c] [PMID: 15027868]
[25]
Binda, C.; Li, M.; Hubalek, F.; Restelli, N.; Edmondson, D.E.; Mattevi, A. Insights into the mode of inhibition of human mitochondrial monoamine oxidase B from high-resolution crystal structures. Proc. Natl. Acad. Sci. USA, 2003, 100(17), 9750-9755.
[http://dx.doi.org/10.1073/pnas.1633804100] [PMID: 12913124]
[26]
Binda, C.; Hubálek, F.; Li, M.; Edmondson, D.E.; Mattevi, A. Crystal structure of human monoamine oxidase B, a drug target enzyme monotopically inserted into the mitochondrial outer membrane. FEBS Lett., 2004, 564(3), 225-228.
[http://dx.doi.org/10.1016/S0014-5793(04)00209-1] [PMID: 15111100]
[27]
Carrieri, A.; Carotti, A.; Barreca, M.L.; Altomare, C. Binding models of reversible inhibitors to type-B monoamine oxidase. J. Comput. Aided Mol. Des., 2002, 16(11), 769-778.
[http://dx.doi.org/10.1023/A:1023815426730] [PMID: 12825788]
[28]
Chimenti, F.; Maccioni, E.; Secci, D.; Bolasco, A.; Chimenti, P.; Granese, A.; Befani, O.; Turini, P.; Alcaro, S.; Ortuso, F.; Cirilli, R.; La Torre, F.; Cardia, M.C.; Distinto, S. Synthesis, molecular modeling studies, and selective inhibitory activity against monoamine oxidase of 1-thiocarbamoyl-3,5-diaryl-4,5-dihydro-(1H)- pyrazole derivatives. J. Med. Chem., 2005, 48(23), 7113-7122.
[http://dx.doi.org/10.1021/jm040903t] [PMID: 16279769]
[29]
Harkcom, W.T.; Bevan, D.R. Molecular docking of inhibitors into monoamine oxidase B. Biochem. Biophys. Res. Commun., 2007, 360(2), 401-406.
[http://dx.doi.org/10.1016/j.bbrc.2007.06.055] [PMID: 17597580]
[30]
Gallardo-Godoy, A.; Fierro, A.; McLean, T.H.; Castillo, M.; Cassels, B.K.; Reyes-Parada, M.; Nichols, D.E. Sulfur-substituted alpha-alkyl phenethylamines as selective and reversible MAO-A inhibitors: biological activities, CoMFA analysis, and active site modeling. J. Med. Chem., 2005, 48(7), 2407-2419.
[http://dx.doi.org/10.1021/jm0493109] [PMID: 15801832]
[31]
Medvedev, A.E.; Veselovsky, A.V.; Shvedov, V.I.; Tikhonova, O.V.; Moskvitina, T.A.; Fedotova, O.A.; Axenova, L.N.; Kamyshanskaya, N.S.; Kirkel, A.Z.; Ivanov, A.S. Inhibition of monoamine oxidase by pirlindole analogues: 3D-QSAR and CoMFA analysis. J. Chem. Inf. Comput. Sci., 1998, 38(6), 1137-1144.
[http://dx.doi.org/10.1021/ci9802068] [PMID: 9845968]
[32]
Chimenti, F.; Bolasco, A.; Manna, F.; Secci, D.; Chimenti, P.; Granese, A.; Befani, O.; Turini, P.; Cirilli, R.; La Torre, F.; Alcaro, S.; Ortuso, F.; Langer, T. 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., 2006, 13(12), 1411-1428.
[http://dx.doi.org/10.2174/092986706776872907] [PMID: 16719786]
[33]
Gnerre, C.; Catto, M.; Leonetti, F.; Weber, P.; Carrupt, P-A.; Altomare, C.; Carotti, A.; Testa, B. Inhibition of monoamine oxidases by functionalized coumarin derivatives: biological activities, QSARs, and 3D-QSARs. J. Med. Chem., 2000, 43(25), 4747-4758.
[http://dx.doi.org/10.1021/jm001028o] [PMID: 11123983]
[34]
Silvestri, R.; La Regina, G.; De Martino, G.; Artico, M.; Befani, O.; Palumbo, M.; Agostinelli, E.; Turini, P. Simple, potent, and selective pyrrole inhibitors of monoamine oxidase types A and B. J. Med. Chem., 2003, 46(6), 917-920.
[http://dx.doi.org/10.1021/jm0256124] [PMID: 12620068]
[35]
La Regina, G.; Silvestri, R.; Artico, M.; Lavecchia, A.; Novellino, E.; Befani, O.; Turini, P.; Agostinelli, E. New pyrrole inhibitors of monoamine oxidase: synthesis, biological evaluation, and structural determinants of MAO-A and MAO-B selectivity. J. Med. Chem., 2007, 50(5), 922-931.
[http://dx.doi.org/10.1021/jm060882y] [PMID: 17256833]
[36]
Ogunrombi, M.O.; Malan, S.F.; Terre’blanche, G.; Castagnoli, N., Jr; Bergh, J.J.; Petzer, J.P. Structure-activity relationships in the inhibition of monoamine oxidase B by 1-methyl-3-phenylpyrroles. Bioorg. Med. Chem., 2008, 16(5), 2463-2472.
[http://dx.doi.org/10.1016/j.bmc.2007.11.059] [PMID: 18065227]
[37]
Manley-King, C.I.; Terre’Blanche, G.; Castagnoli, N., Jr; Bergh, J.J.; Petzer, J.P. Inhibition of monoamine oxidase B by N-methyl-2-phenylmaleimides. Bioorg. Med. Chem., 2009, 17(8), 3104-3110.
[http://dx.doi.org/10.1016/j.bmc.2009.03.005] [PMID: 19324554]
[38]
Evranos-Aksöz, B.; Yabanoğlu-Çiftçi, S.; Uçar, G.; Yelekçi, K.; Ertan, R. Synthesis of some novel hydrazone and 2-pyrazoline derivatives: monoamine oxidase inhibitory activities and docking studies. Bioorg. Med. Chem. Lett., 2014, 24(15), 3278-3284.
[http://dx.doi.org/10.1016/j.bmcl.2014.06.015] [PMID: 24986657]
[39]
Chimenti, F.; Fioravanti, R.; Bolasco, A.; Manna, F.; Chimenti, P.; Secci, D.; Befani, O.; Turini, P.; Ortuso, F.; Alcaro, S. Monoamine oxidase isoform-dependent tautomeric influence in the recognition of 3,5-diaryl pyrazole inhibitors. J. Med. Chem., 2007, 50(3), 425-428.
[http://dx.doi.org/10.1021/jm060868l] [PMID: 17266193]
[40]
Youdim, M.B.H.; Bakhle, Y.S. Monoamine oxidase: isoforms and inhibitors in Parkinson’s disease and depressive illness. Br. J. Pharmacol., 2006, 147(Suppl. 1), S287-S296.
[http://dx.doi.org/10.1038/sj.bjp.0706464] [PMID: 16402116]
[41]
Chimenti, F.; Bolasco, A.; Manna, F.; Secci, D.; Chimenti, P.; Befani, O.; Turini, P.; Giovannini, V.; Mondovì, B.; Cirilli, R.; La Torre, F. Synthesis and selective inhibitory activity of 1-acetyl-3,5-diphenyl-4,5-dihydro-(1H)-pyrazole derivatives against monoamine oxidase. J. Med. Chem., 2004, 47(8), 2071-2074.
[http://dx.doi.org/10.1021/jm031042b] [PMID: 15056004]
[42]
Chimenti, F.; Bolasco, A.; Manna, F.; Secci, D.; Chimenti, P.; Granese, A.; Befani, O.; Turini, P.; Alcaro, S.; Ortuso, F. Synthesis and molecular modelling of novel substituted-4,5-dihydro-(1H)-pyrazole derivatives as potent and highly selective monoamine oxidase-A inhibitors. Chem. Biol. Drug Des., 2006, 67(3), 206-214.
[http://dx.doi.org/10.1111/j.1747-0285.2006.00367.x] [PMID: 16611214]
[43]
Chimenti, F.; Fioravanti, R.; Bolasco, A.; Manna, F.; Chimenti, P.; Secci, D.; Rossi, F.; Turini, P.; Ortuso, F.; Alcaro, S.; Cardia, M.C. Synthesis, molecular modeling studies and selective inhibitory activity against MAO of N1-propanoyl-3,5-diphenyl-4,5-dihydro-(1H)-pyrazole derivatives. Eur. J. Med. Chem., 2008, 43(10), 2262-2267.
[http://dx.doi.org/10.1016/j.ejmech.2007.12.026] [PMID: 18281126]
[44]
Chimenti, F.; Maccioni, E.; Secci, D.; Bolasco, A.; Chimenti, P.; Granese, A.; Befani, O.; Turini, P.; Alcaro, S.; Ortuso, F.; Cirilli, R.; La Torre, F.; Cardia, M.C.; Distinto, S. Synthesis, molecular modeling studies, and selective inhibitory activity against monoamine oxidase of 1-thiocarbamoyl-3,5-diaryl-4,5-dihydro-(1H)- pyrazole derivatives. J. Med. Chem., 2005, 48(23), 7113-7122.
[http://dx.doi.org/10.1021/jm040903t] [PMID: 16279769]
[45]
Palaska1, E.; Aydin1, F.; Uçar, G.; Erol, D. synthesis and monoamine oxidase inhibitory activities of 1-thiocarbamoyl-3,5-diphenyl-4,5-dihydro-1h-pyrazole derivatives. Arch. Pharm. Chem. Life Sci., 2008, 341, 209-215.
[http://dx.doi.org/10.1002/ardp.200700159]
[46]
Gökhan-Kelekc, N.; Yabanoğlu, S.; Küpeli, E. Salgın, U.; Ögen, Ö.; Uçar, G.; Yeşilada, E.; Kendi, E.; Yeşiladaf, A.; Bilgina A. A.. A new therapeutic approach in Alzheimer disease: Some novel pyrazole derivatives as dual MAO-B inhibitors and anti-inflammatory analgesics. Bioorg. Med. Chem., 2007, 15, 5775-5786.
[http://dx.doi.org/10.1016/j.bmc.2007.06.004] [PMID: 17611112]
[47]
Jayaprakash, V.; Sinha, B.N.; Uçar, G.; Ercan, A. Pyrazoline-based mycobactin analogues as MAO-inhibitors. Bioorg. Med. Chem. Lett., 2008, 18(24), 6362-6368.
[http://dx.doi.org/10.1016/j.bmcl.2008.10.084] [PMID: 18980841]
[48]
Harkcom, W.T.; Bevan, D.R. Molecular docking of inhibitors into monoamine oxidase B. Biochem. Biophys. Res. Commun., 2007, 360(2), 401-406.
[http://dx.doi.org/10.1016/j.bbrc.2007.06.055] [PMID: 17597580]
[49]
Boppana, K.; Dubey, P.K.; Jagarlapudi, S.A.; Vadivelan, S.; Rambabu, G. Knowledge based identification of MAO-B selective inhibitors using pharmacophore and structure based virtual screening models. Eur. J. Med. Chem., 2009, 44(9), 3584-3590.
[http://dx.doi.org/10.1016/j.ejmech.2009.02.031] [PMID: 19321235]
[50]
Sahoo, A.; Yabanoglu, S.; Sinha, B.N.; Ucar, G.; Basu, A.; Jayaprakash, V. Towards development of selective and reversible pyrazoline based MAO-inhibitors: Synthesis, biological evaluation and docking studies. Bioorg. Med. Chem. Lett., 2010, 20(1), 132-136.
[http://dx.doi.org/10.1016/j.bmcl.2009.11.015] [PMID: 19945874]
[51]
Karuppasamy, M.; Mahapatra, M.; Yabanoglu, S.; Ucar, G.; Sinha, B.N.; Basu, A.; Mishra, N.; Sharon, A.; Kulandaivelu, U.; Jayaprakash, V. Development of selective and reversible pyrazoline based MAO-A inhibitors: Synthesis, biological evaluation and docking studies. Bioorg. Med. Chem., 2010, 18(5), 1875-1881.
[http://dx.doi.org/10.1016/j.bmc.2010.01.043] [PMID: 20149663]
[52]
Fioravanti, R.; Bolasco, A.; Manna, F.; Rossi, F.; Orallo, F.; Yáñez, M.; Vitali, A.; Ortuso, F.; Alcaro, S. Synthesis and molecular modelling studies of prenylated pyrazolines as MAO-B inhibitors. Bioorg. Med. Chem. Lett., 2010, 20(22), 6479-6482.
[http://dx.doi.org/10.1016/j.bmcl.2010.09.061] [PMID: 20934874]
[53]
Maccioni, E.; Alcaro, S.; Orallo, F.; Cardia, M.C.; Distinto, S.; Costa, G.; Yanez, M.; Sanna, M.L.; Vigo, S.; Meleddu, R.; Secci, D. Synthesis of new 3-aryl-4,5-dihydropyrazole-1-carbothioamide derivatives. An investigation on their ability to inhibit monoamine oxidase. Eur. J. Med. Chem., 2010, 45(10), 4490-4498.
[http://dx.doi.org/10.1016/j.ejmech.2010.07.009] [PMID: 20702005]
[54]
Chimenti, F.; Carradori, S.; Secci, D.; Bolasco, A.; Bizzarri, B.; Chimenti, P.; Granese, A.; Yáñez, M.; Orallo, F. 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., 2010, 45(2), 800-804.
[http://dx.doi.org/10.1016/j.ejmech.2009.11.003] [PMID: 19926363]
[55]
Jagrat, M.; Behera, J.; Yabanoglu, S.; Ercan, A.; Ucar, G.; Sinha, B.N.; Sankaran, V.; Basu, A.; Jayaprakash, V. Pyrazoline based MAO inhibitors: synthesis, biological evaluation and SAR studies. Bioorg. Med. Chem. Lett., 2011, 21(14), 4296-4300.
[http://dx.doi.org/10.1016/j.bmcl.2011.05.057] [PMID: 21680183]
[56]
Mishra, N.; Sasmal, D. Modulations of brain amines and dopaminergic behavior by a novel, reversible and selective MAO-B inhibitor. Brain Res., 2012, 1470, 45-51.
[http://dx.doi.org/10.1016/j.brainres.2012.06.037] [PMID: 22765918]
[57]
Vishnu Nayak, B.; Ciftci-Yabanoglu, S.; Jadav, S.S.; Jagrat, M.; Sinha, B.N.; Ucar, G.; Jayaprakash, V. Monoamine oxidase inhibitory activity of 3,5-biaryl-4,5-dihydro-1H-pyrazole-1-carboxylate derivatives. Eur. J. Med. Chem., 2013, 69, 762-767.
[http://dx.doi.org/10.1016/j.ejmech.2013.09.010] [PMID: 24099995]
[58]
Mathew, B.; Suresh, J.; Anbazhagan, S.; Devd, S. Proposed interaction of some novel antidepressant pyrazolines against monoamine oxidase isoforms. Molecular docking studies and PASS assisted in silico approach. Biomed. Aging Pathol., 2014, 4, 297-301.
[http://dx.doi.org/10.1016/j.biomag.2014.07.011]
[59]
Tong, X.; Chen, R.; Zhang, T.T.; Han, Y.; Tang, W.J.; Liu, X.H. Design and synthesis of novel 2-pyrazoline-1-ethanone derivatives as selective MAO inhibitors. Bioorg. Med. Chem., 2015, 23(3), 515-525.
[http://dx.doi.org/10.1016/j.bmc.2014.12.010] [PMID: 25541201]
[60]
Sant’ Anna. , G. S.; Machado, P.; Sauzem, P. D.; Rosa, F. A.; Rubin, M. A.; Ferreira, J. Bonacorso, H. G.; Zanatta, N.; Martins, M. A. P.. Ultrasound promoted synthesis of 2-imidazolines in water: A greener approach toward monoamine oxidase inhibitors. Bioorg. Med. Chem. Lett., 2009, 19, 546-549.
[http://dx.doi.org/10.1016/j.bmcl.2008.03.001]
[61]
Villarinho, J.G.; Fachinetto, R.; de Vargas Pinheiro, F.; da Silva Sant’Anna, G.; Machado, P.; Dombrowski, P.A.; da Cunha, C.; de Almeida Cabrini, D.; Pinto Martins, M.A.; Gauze Bonacorso, H.; Zanatta, N.; Antonello Rubin, M.; Ferreira, J. Antidepressant-like effect of the novel MAO inhibitor 2-(3,4-dimethoxy-phenyl)-4,5-dihydro-1H-imidazole (2-DMPI) in mice. Prog. Neuropsychopharmacol. Biol. Psychiatry, 2012, 39(1), 31-39.
[http://dx.doi.org/10.1016/j.pnpbp.2012.04.007] [PMID: 22525823]
[62]
Kaplan, A.P.; Keenan, T.; Scott, R.; Zhou, X.; Bourchouladze, R.; McRiner, A.J.; Wilson, M.E.; Romashko, D.; Miller, R.; Bletsch, M.; Anderson, G.; Stanley, J.; Zhang, A.; Lee, D.; Nikpur, J. Identification of 5-(1-Methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)thiophene-2-Carboxamides as novel and selective monoamine oxidase B inhibitors used to improve memory and cognition. ACS Chem. Neurosci., 2017, 8(12), 2746-2758.
[http://dx.doi.org/10.1021/acschemneuro.7b00282] [PMID: 28857544]
[63]
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(16), 4874-4880.
[http://dx.doi.org/10.1021/jm800132g] [PMID: 18666768]
[64]
Chimenti, F.; Bolasco, A.; Secci, D.; Chimenti, P.; Granese, A.; Carradori, S.; Yáñez, 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(15), 5715-5723.
[http://dx.doi.org/10.1016/j.bmc.2010.06.007] [PMID: 20615716]
[65]
Chimenti, F.; Secci, D.; Bolasco, A.; Chimenti, P.; Granese, A.; Carradori, S.; Maccioni, E.; Cardia, M.C.; Yáñez, M.; Orallo, F.; Alcaro, S.; Ortuso, F.; Cirilli, R.; Ferretti, R.; Distinto, S.; Kirchmair, J.; Langer, T. Synthesis, semipreparative HPLC separation, biological evaluation, and 3D-QSAR of hydrazothiazole derivatives as human monoamine oxidase B inhibitors. Bioorg. Med. Chem., 2010, 18(14), 5063-5070.
[http://dx.doi.org/10.1016/j.bmc.2010.05.070] [PMID: 20579890]
[66]
Distinto, S.; Yáñez, M.; Alcaro, S.; Cardia, M.C.; Gaspari, M.; Sanna, M.L.; Meleddu, R.; Ortuso, F.; Kirchmair, J.; Markt, P.; Bolasco, A.; Wolber, G.; Secci, D.; Maccioni, E. Synthesis and biological assessment of novel 2-thiazolylhydrazones and computational analysis of their recognition by monoamine oxidase B. Eur. J. Med. Chem., 2012, 48, 284-295.
[http://dx.doi.org/10.1016/j.ejmech.2011.12.027] [PMID: 22222137]
[67]
Secci, D.; Bolasco, A.; Carradori, S.; D’Ascenzio, M.; Nescatelli, R.; Yáñez, M. Recent advances in the development of selective human MAO-B inhibitors: (hetero)arylidene-(4-substituted-thiazol-2-yl)hydrazines. Eur. J. Med. Chem., 2012, 58, 405-417.
[http://dx.doi.org/10.1016/j.ejmech.2012.10.032] [PMID: 23153812]
[68]
Geldenhuys, W.J.; Darvesh, A.S.; Funk, M.O.; Van der Schyf, C.J.; Carroll, R.T. Identification of novel monoamine oxidase B inhibitors by structure-based virtual screening. Bioorg. Med. Chem. Lett., 2010, 20(17), 5295-5298.
[http://dx.doi.org/10.1016/j.bmcl.2010.06.128] [PMID: 20650633]
[69]
Tripathi, R.K.P.; M Sasi, V.; Gupta, S.K.; Krishnamurthy, S.; Ayyannan, S.R. Design, synthesis, and pharmacological evaluation of 2-amino-5-nitrothiazole derived semicarbazones as dual inhibitors of monoamine oxidase and cholinesterase: effect of the size of aryl binding site. J. Enzyme Inhib. Med. Chem., 2018, 33(1), 37-57.
[http://dx.doi.org/10.1080/14756366.2017.1389920] [PMID: 29098902]
[70]
Robinson, S.J.; Petzer, J.P.; Petzer, A.; Bergh, J.J.; Lourens, A.C.U. Selected furanochalcones as inhibitors of monoamine oxidase. Bioorg. Med. Chem. Lett., 2013, 23(17), 4985-4989.
[http://dx.doi.org/10.1016/j.bmcl.2013.06.050] [PMID: 23860591]
[71]
Minders, C.; Petzer, J.P.; Petzer, A.; Lourens, A.C.U. Monoamine oxidase inhibitory activities of heterocyclic chalcones. Bioorg. Med. Chem. Lett., 2015, 25(22), 5270-5276.
[http://dx.doi.org/10.1016/j.bmcl.2015.09.049] [PMID: 26432037]
[72]
Juárez-Jiménez, J.; Mendes, E.; Galdeano, C.; Martins, C.; Silva, D.B.; Marco-Contelles, J.; do Carmo Carreiras, M.; Luque, F.J.; Ramsay, R.R. Exploring the structural basis of the selective inhibition of monoamine oxidase A by dicarbonitrile aminoheterocycles: role of Asn181 and Ile335 validated by spectroscopic and computational studies. Biochim. Biophys. Acta, 2014, 1844(2), 389-397.
[http://dx.doi.org/10.1016/j.bbapap.2013.11.003] [PMID: 24247011]
[73]
Ke, S.Y.; Qian, X.H.; Liu, F.Y.; Wang, N.; Yang, Q.; Li, Z. Novel 4H-1,3,4-oxadiazin-5(6H)-ones with hydrophobic and long alkyl chains: design, synthesis, and bioactive diversity on inhibition of monoamine oxidase, chitin biosynthesis and tumor cell. Eur. J. Med. Chem., 2009, 44(5), 2113-2121.
[http://dx.doi.org/10.1016/j.ejmech.2008.10.015] [PMID: 19027994]
[74]
Lühr, S.; Vilches-Herrera, M.; Fierro, A.; Ramsay, R.R.; Edmondson, D.E.; Reyes-Parada, M.; Cassels, B.K.; Iturriaga-Vásquez, P. 2-Arylthiomorpholine derivatives as potent and selective monoamine oxidase B inhibitors. Bioorg. Med. Chem., 2010, 18(4), 1388-1395.
[http://dx.doi.org/10.1016/j.bmc.2010.01.029] [PMID: 20123154]
[75]
Kaya, B.; Yurttaş, L.; Sağlik, B.N.; Levent, S.; Özkay, Y.; Kaplancikli, Z.A. Novel 1-(2-pyrimidin-2-yl)piperazine derivatives as selective monoamine oxidase (MAO)-A inhibitors. J. Enzyme Inhib. Med. Chem., 2017, 32(1), 193-202.
[http://dx.doi.org/10.1080/14756366.2016.1247054] [PMID: 28097890]
[76]
Meleddu, R.; Distinto, S.; Cirilli, R.; Alcaro, S.; Yanez, M.; Sanna, M.L.; Corona, A.; Melis, C.; Bianco, G.; Matyus, P.; Cottiglia, F.; Maccioni, E. Through scaffold modification to 3,5-diaryl-4,5-dihydroisoxazoles: new potent and selective inhibitors of monoamine oxidase B. J. Enzyme Inhib. Med. Chem., 2017, 32(1), 264-270.
[http://dx.doi.org/10.1080/14756366.2016.1247061] [PMID: 28097874]
[77]
Kumar, B.; Sheetal, ; Mantha, A.K.; Kumar, V. Synthesis, biological evaluation and molecular modeling studies of phenyl-/benzhydrylpiperazine derivatives as potential MAO inhibitors. Bioorg. Chem., 2018, 77, 252-262.
[http://dx.doi.org/10.1016/j.bioorg.2018.01.020] [PMID: 29421700]
[78]
Ferrazzano, L.; Viola, A.; Lonati, E.; Bulbarelli, A.; Musumeci, R.; Cocuzza, C.; Lombardo, M.; Tolomelli, A. New isoxazolidinone and 3,4-dehydro-β-proline derivatives as antibacterial agents and MAO-inhibitors: A complex balance between two activities. Eur. J. Med. Chem., 2016, 124, 906-919.
[http://dx.doi.org/10.1016/j.ejmech.2016.09.007] [PMID: 27676470]
[79]
Di Pietro, O.; Alencar, N.; Esteban, G.; Viayna, E.; Szałaj, N.; Vázquez, J.; Juárez-Jiménez, J.; Sola, I.; Pérez, B.; Solé, M.; Unzeta, M.; Muñoz-Torrero, D.; Luque, F.J. Design, synthesis and biological evaluation of N-methyl-N-[(1,2,3-triazol-4-yl)alkyl]propargylamines as novel monoamine oxidase B inhibitors. Bioorg. Med. Chem., 2016, 24(20), 4835-4854.
[http://dx.doi.org/10.1016/j.bmc.2016.06.045] [PMID: 27396685]
[80]
Li, F.; Wang, Z.M.; Wu, J.J.; Wang, J.; Xie, S.S.; Lan, J.S.; Xu, W.; Kong, L.Y.; Wang, X.B. Synthesis and pharmacological evaluation of donepezil-based agents as new cholinesterase/monoamine oxidase inhibitors for the potential application against Alzheimer’s disease. J. Enzyme Inhib. Med. Chem., 2016, 31(Suppl. 3), 41-53.
[http://dx.doi.org/10.1080/14756366.2016.1201814] [PMID: 27384289]
[81]
Lee, J.; Lee, Y.; Park, S.J.; Lee, J.; Kim, Y.S.; Suh, Y.G.; Lee, J. Discovery of highly selective and potent monoamine oxidase B inhibitors: Contribution of additional phenyl rings introduced into 2-aryl-1,3,4-oxadiazin-5(6H)-one. Eur. J. Med. Chem., 2017, 130, 365-378.
[http://dx.doi.org/10.1016/j.ejmech.2017.02.059] [PMID: 28273563]
[82]
Im, W.B.; Choi, S.H.; Park, J.Y.; Choi, S.H.; Finn, J.; Yoon, S.H. Discovery of torezolid as a novel 5-hydroxymethyl-oxazolidinone antibacterial agent. Eur. J. Med. Chem., 2011, 46(4), 1027-1039.
[http://dx.doi.org/10.1016/j.ejmech.2011.01.014] [PMID: 21292356]
[83]
Košak, U.; Knez, D.; Coquelle, N.; Brus, B.; Pišlar, A.; Nachon, F.; Brazzolotto, X.; Kos, J.; Colletier, J.P.; Gobec, S. N-Propargylpiperidines with naphthalene-2-carboxamide or naphthalene-2-sulfonamide moieties: Potential multifunctional anti-Alzheimer’s agents. Bioorg. Med. Chem., 2017, 25(2), 633-645.
[http://dx.doi.org/10.1016/j.bmc.2016.11.032] [PMID: 27908752]

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy