Synthesis and monoamine oxidase A/B inhibitory evaluation of new benzothiazole-thiazolylhydrazine derivatives

References

• Carradori, S.; Secci, D.; Petzer, J.-P. MAO Inhibitors and Their Wider Applications: A Patent Review. Exp. Opin. Ther. Pat. 2018, 28, 211–226. DOI: 10.1080/13543776.2018.1427735.
   PubMed Web of Science ®Google Scholar
• Rang, H.-P.; Dale, M.-M.; Ritter, J.-M.; Flower, R.-J. In Pharmacology; Churchill Livingstone, Elsevier: London, 2008; p 174.
   Google Scholar
• Tripton, K.-F. Enzymology of Monoamine Oxidase. Cell. Biochem. Funct. 1986, 4, 79–87. DOI: 10.1002/cbf.290040202.
   PubMed Web of Science ®Google Scholar
• Ramsay, R.-R. Inhibitor Design for Monoamine Oxidases. Curr. Pharm. Des. 2013, 19, 2529–2539. DOI: 10.2174/1381612811319140004.
   PubMed Web of Science ®Google Scholar
• Mathew, B.; Baek, S.-C.; Parambi, D.-G.-T.; Lee, J.-P.; Joy, M.; Rilda, P.-R.-A.; Randev, R.-V.; Nithyamol, P.; Vijayan, V.; Inasu, S.-T.; et al. New Frontiers in Selective Human MAO-B Inhibitors. Med. Chem. Commun. 2018, 9, 1871–1881. DOI: 10.1021/jm501690r.
   Google Scholar
• Shih, J.-C.; Chen, K.; Ridd, M.-J. Monoamine Oxidase: From Genes to Behavior. Annu. Rev. Neurosci. 1999, 22, 197–217. DOI: 10.1146/annurev.neuro.22.1.197.
   PubMed Web of Science ®Google Scholar
• Son, S.-Y.; Ma, J.; Kondou, Y.; Yoshimura, M.; Yamashita, E.; Tsukihara, T. Structure of Human Monoamine Oxidase A at 2.2-Å Resolution: The Control of Opening the Entry for Substrates/Inhibitors. Proc. Natl. Acad. Sci. USA 2008, 105, 5739–5744. DOI: 10.1073/pnas.0710626105.
   PubMed Web of Science ®Google Scholar
• Fowler, C.-J.; Wiberg, A.; Oreland, L.; Marcusson, J.; Winblad, B. The Effect of Age on the Activity and Molecular Properties of Human Brain Monoamine Oxidase. J. Neur. Transm. 1980, 49, 1–20. DOI: 10.1007/BF01249185.
   PubMed Web of Science ®Google Scholar
• Saura, J.; Luque, J.-M.; Cesura, A.-M.; Da Prada, M.; Chan-Palay, V.; Huber, G.; Loffler, J.; Richards, J.-G. Increased Monoamine Oxidase B Activity in Plaque-Associated Astrocytes of Alzheimer Brains Revealed by Quantitative Enzyme Radioautography. Neuroscience 1994, 62, 15–30. DOI: 10.1016/0306-4522(94)90311-5.
   PubMed Web of Science ®Google Scholar
• Tripathi, R.-K.-P.; Ayyannan, S. R. Design, Synthesis, and Evaluation of 2‐Amino‐6‐Nitrobenzothiazole‐Derived Hydrazones as MAO Inhibitors: Role of the Methylene Spacer Group. ChemMedChem 2016, 11, 1551–1567. DOI: 10.1002/cmdc.201600202.
   PubMed Web of Science ®Google Scholar
• Finberg, J.-P.-M. Update on the Pharmacology of Selective Inhibitors of MAO-A and MAO-B: Focus on Modulation of CNS Monoamine Neurotransmitter Release. Pharmacol. Ther. 2014, 143, 133–152. DOI: 10.1016/j.pharmthera.2014.02.0102.
   PubMed Web of Science ®Google Scholar
• Tripathi, A. C.; Upadhyay, S.; Paliwal, S.; Saraf, S. K. Privileged Scaffolds as MAO Inhibitors: Retrospect and Prospects. Eur. J. Med. Chem. 2018, 145, 445–497. DOI: 10.1016/j.ejmech.2018.01.003.
   PubMed Web of Science ®Google Scholar
• Huang, C.; Xiong, J.; Guan, H.-D.; Wang, C.-H.; Lei, X.; Hu, J.-F. Discovery, Synthesis, Biological Evaluation and Molecular Docking Study of (R)-5-Methylmellein and Its Analogs as Selective Monoamine Oxidase A Inhibitors. Bioorg. Med. Chem. 2019, 27, 2027–2040. DOI: 10.1016/j.bmc.2019.03.060.
   PubMedGoogle Scholar
• Brehme, R.; Enders, D.; Fernandez, R.; Lassaletta, J.-M. Aldehyde N,N‐Dialkylhydrazones as Neutral Acyl Anion Equivalents: Umpolung of the Imine Reactivity. Eur. J. Org. Chem. 2007, 2007, 5629–5660. DOI: 10.1002/ejoc.200700746.
   Web of Science ®Google Scholar
• Belskaya, N.-P.; Dehaen, W.; Bakulev, V.-A. Synthesis and Properties of Hydrazones Bearing Amide, Thioamide and Amidine Functions. Arkivoc 2010, 275–332. DOI: http://dx.doi.org/10.3998/ark.5550190.0011.108.
   Web of Science ®Google Scholar
• Mc Kenna, K.-F.; Baker, G.-B.; Coutta, R.-T. N2-Acetylphenelzine: Effects on Rat Brain GABA, Alanine and Biogenic Amines. Arch. Pharmacol. 1991, 343, 478–482. DOI: 10.1007/BF00169549.
   Google Scholar
• Yamada, N.; Takahashi, S.; Todd, K. G.; Baker, G. B.; Paetsch, P. R. Multiple-Layer, Direct-Compression, Controlled-Release System: In Vitro and In Vivo Evaluation. J. Pharm. Sci. 1993, 82, 934–937. DOI: 10.1002/jps.2600820715.
   PubMed Web of Science ®Google Scholar
• Chimenti, F.; Maccioni, E.; Secci, D.; Bolasco, A.; Chimenti, P.; Granese, A.; Befani, O.; Turini, P.; Alcaro, S.; Ortuso, F.; et al. Selective Inhibitory Activity Against MAO and Molecular Modeling Studies of 2-Thiazolylhydrazone Derivatives. J. Med. Chem. 2007, 50, 707–712. DOI: 10.1021/jm060869d.
   PubMed Web of Science ®Google Scholar
• Binda, C.; Wang, J.; Li, M.; Hubalek, F.; Mattevi, A.; Edmondson, D. E. Structural and Mechanistic Studies of Arylalkylhydrazine Inhibition of Human Monoamine Oxidases A and B. Biochemistry 2008, 47, 5616–5625. DOI: 10.1021/bi8002814.
   PubMed Web of Science ®Google Scholar
• Kumar, B.; Sheetal, S.; Mantha, A. K.; Kumar, V. Recent Developments on the Structure–Activity Relationship Studies of MAO Inhibitors and Their Role in Different Neurological Disorders. RSC Adv. 2016, 6, 42660–42683. DOI: 10.1039/C6RA00302H.
   Web of Science ®Google Scholar
• D’Ascenzio, M.; Carradori, S.; Secci, D.; Mannina, L.; Soboley, A.-P. D.; Monte, C.; Cirilli, R.; Yanez, M.; Alcaro, S.; Ortuso, F. Identification of the Stereochemical Requirements in the 4-Aryl-2-Cycloalkylidenhydrazinylthiazole Scaffold for the Design of Selective Human Monoamine Oxidase B Inhibitors. Bioorg. Med. Chem. 2014, 22, 2887–2895. DOI: 10.1016/j.bmc.2014.03.042.
   PubMed Web of Science ®Google Scholar
• D’Ascenzio, M.; Chimenti, P.; Gidaro, M.-C.; De Monte, C.; De Vita, D.; Granese, A.; Scipione, L.; Di Santo, R.; Costa, G.; Alcaro, S.; et al. Thiazol-2-yl)Hydrazone Derivatives from Acetylpyridines as Dual Inhibitors of MAO and AChE: Synthesis, Biological Evaluation and Molecular Modeling Studies. J. Enzyme Inhib. Med. Chem. 2015, 30, 908–919. DOI: 10.3109/14756366.2014.987138.
   PubMed Web of Science ®Google Scholar
• Secci, D.; Bolasco, A.; Carradori, S.; Ascenzio, M.-D.; Nescatelli, R.; Yanez, M. Synthesis, Anti-Candida Activity, and Cytotoxicity of New (4-(4-Iodophenyl)Thiazol-2-yl)Hydrazine Derivatives. Eur. J. Med. Chem. 2012, 58, 405–417. DOI: 10.1016/j.ejmech.2012.04.006.
   PubMed Web of Science ®Google Scholar
• Raciti, G.; Mazzone, P.; Raudino, A.; Mazzone, G.; Cambria, A. Inhibition of Rat Liver Mitochondrial Monoamine Oxidase by Hydrazine-Thiazole Derivatives: Structure-Activity Relationships. Bioorg. Med. Chem. 1995, 3, 1485–1491. DOI: 10.1016/0968-0896(95)00137-6.
   PubMed Web of Science ®Google Scholar
• Chimenti, F.; Maccioni, E.; Secci, D.; Bolasco, A.; Chimenti, P.; Granese, A.; Befani, O.; Turini, P.; Alcaro, S.; Ortuso, F.; et al. 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. 2010, 53, 6516–6520. DOI: 10.1021/jm100120s.
   PubMed Web of Science ®Google Scholar
• Chimenti, F.; Secci, D.; Bolasco, A.; Chimenti, P.; Granese, A.; Carradori, S.; Maccioni, E.; Cardia, M. C.; Yanez, M.; Orallo, F.; et al. Synthesis, Semipreparative HPLC Separation, Biological Evaluation, and 3D-QSAR of Hydrazothiazole Derivatives as Human Monoamine Oxidase B Inhibitors. Bioorg. Med. Chem. 2010, 18, 5063–5070. DOI: 10.1016/j.bmc.2010.05.070.
   PubMed Web of Science ®Google Scholar
• Chimenti, F.; Secci, D.; Bolasco, A.; 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. DOI: 10.1016/j.bmc.2010.06.007.
   PubMed Web of Science ®Google Scholar
• Can, N. Ö.; Osmaniye, D.; Levent, S.; Sağlık, B. N.; Korkut, B.; Atlı, Ö.; Özkay, Y.; Kaplancıklı, Z. A. Design, Synthesis and Biological Assessment of New Thiazolylhydrazine Derivatives as Selective and Reversible hMAO-a Inhibitors. Eur. J. Med. Chem. 2018, 144, 68–81. DOI: 10.1016/j.ejmech.2017.12.013.
   PubMed Web of Science ®Google Scholar
• Ilgın, S.; Osmaniye, D.; Levent, S.; Sağlık, B.; Acar Çevik, U.; Çavuşoğlu, B.; Ozkay, Y.; Kaplancıklı, Z. Design and Synthesis of New Benzothiazole Compounds as Selective hMAO-B Inhibitors. Molecules 2017, 22, 2187. DOI: 10.3390/molecules22122187.
   Web of Science ®Google Scholar
• Can, Ö. D.; Osmaniye, D.; Demir Özkay, Ü.; Sağlık, B. N.; Levent, S.; Ilgın, S.; Baysal, M.; Özkay, Y.; Kaplancıklı, Z. A. MAO Enzymes Inhibitory Activity of New Benzimidazole Derivatives Including Hydrazone and Propargyl Side Chains. Eur. J. Med. Chem. 2017, 131, 92–106. DOI: 10.1016/j.ejmech.2017.03.009.
   PubMed Web of Science ®Google Scholar
• Saglık, B.-N.; Kaya Cavusoglu, B.; Osmaniye, D.; Levent, S.; Acar Cevik, U.; Ilgın, S.; Ozkay, Y.; Kaplancıklı, Z. A.; Ozturk, Y. In Vitro and In Silico Evaluation of New Thiazole Compounds as Monoamine Oxidase Inhibitors. Bioorg. Chem. 2019, 85, 97–108. DOI: 10.1016/j.bioorg.2018.12.019.
   PubMed Web of Science ®Google Scholar