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Research Paper

Benzo[b]tiophen-3-ol derivatives as effective inhibitors of human monoamine oxidase: design, synthesis, and biological activity

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Pages 1511-1525 | Received 04 Jul 2019, Accepted 02 Aug 2019, Published online: 19 Aug 2019

References

  • Grimsby J, Chen K, Wang LJ, et al. Human monoamine oxidase A and B genes exhibit identical exon-intron organization. Proc Natl Acad Sci USA 1991;88:3637–41.
  • Chen K, Shih JC. Monoamine oxidase A and B: structure, function, and behavior. Adv Pharmacol 1998;42:292–6.
  • Wimbiscus M, Kostenko O, Malone D. MAO inhibitors: risks, benefits, and lore. Clev Clin J Med 2010;77:859–82.
  • (a) Carradori S, Secci D, Petzer JP. MAO inhibitors and their wider applications: a patent review. Expert Opin Ther Pat 2018;28:211–26. (b) Carradori S, Secci D, Bolasco A, et al. Patent-related survey on new monoamine oxidase inhibitors and their therapeutic potential. Expert Opin Ther Pat 2012;22:759–801. (c) Bolasco A, Carradori S, Fioravanti R. Focusing on new monoamine oxidase inhibitors. Expert Opin Ther Pat 2010;20:909–39. (d) Guglielmi P, Carradori S, Ammazzalorso A, Secci D. Novel approaches to the discovery of selective human monoamine oxidase-B inhibitors: is there room for improvement? Expert Opin Drug Discov 2019;1–41.
  • Lamensdorf I, Eisenhofer G, Harvey-White J, et al. 3,4-Dihydroxyphenylacetaldehyde potentiates the toxic effects of metabolic stress in PC12 cells. Brain Res 2000;868:191–201.
  • Winterbourn CC. Toxicity of iron and hydrogen peroxide: the Fenton reaction. Toxicol Lett 1995;82–83:969–74.
  • Youdim M. Monoamine oxidase inhibitors, and iron chelators in depressive illness and neurodegenerative diseases. J Neural Transm 2018;125:1719–33.
  • Tipton KF. 90 Years of monoamine oxidase: some progress and some confusion. J Neural Transm 2018;125:1519–51.
  • Marconi GD, Gallorini M, Carradori S, et al. The up-pegulation of oxidative stress as a potential mechanism of novel MAO-B inhibitors for glioblastoma treatment. Molecules 2019;24:2005.
  • Xuan M, Guan X, Gu Q. Different iron deposition patterns in early- and middle-late-onset Parkinson’s disease. Park Relat Disord 2017;44:23–7.
  • Carradori S, Silvestri R. New frontiers in selective human MAO-B inhibitors. J Med Chem 2015;58:6717–32.
  • Carradori S, D’Ascenzio M, Chimenti P, et al. Selective MAO-B inhibitors: a lesson from natural products. Mol Divers 2014;18:219–43.
  • Wouters J. Structural aspects of monoamine oxidase and its reversible inhibition. Curr Med Chem 1998;5:137–62.
  • Medvedev AE, Ivanov AS, Kamyshanskaya NS, et al. Interaction of indole derivatives with monoamine oxidase A and B. Studies on the structure-inhibitory activity relationship. Biochem Mol Biol Int 1995;36:113–22.
  • Binda C, Li M, Hubalek F, et al. Insights into the mode of inhibition of human mitochondrial monoamine oxidase B from high-resolution crystal structures. Proc Natl Acad Sci USA 2003;100:9750–5.
  • Morales-Camilo N, Salas CO, Sanhueza C, et al. Synthesis, biological evaluation, and molecular simulation of chalcones and aurones as selective MAO-B inhibitors. Chem Biol Drug Des 2015;85:685–95.
  • Nel MS, Petzer A, Petzer JP, Legoabe LJ. 2-Heteroarylidene-1-indanone derivatives as inhibitors of monoamine oxidase. Bioorg Chem 2016;69:20–8.
  • Nel MS, Petzer A, Petzer JP, Legoabe LJ. 2-Benzylidene-1-indanone derivatives as inhibitors of monoamine oxidase. Bioorg Med Chem Lett 2016;26:4599–605.
  • Chimenti F, Fioravanti R, Bolasco A, et al. Chalcones: a valid scaffold for monoamine oxidases inhibitors. J Med Chem 2009;52:2818–24.
  • Uzoukwu BA. Some metal complexes of 1,3-diketone: syntheses, UV-Vis, IR, 1H, 13C and 19F NMR spectral studies of the complexes of U(VI), Fe(III), V(V) and Ca(II) with 2-thenoyltrifluoroacetone (HTTA). Inorg Chim Acta 1990;176:143–8.
  • Budimir A. Metal ions, Alzheimer’s disease and chelation therapy. Acta Pharm 2011;61:1–14.
  • Ward RJ, Dexter DT, Crichton RR. Chelating agents for neurodegenerative diseases. Curr Med Chem 2012;19:2760–72.
  • Trapani P, Kvapil L, Hradil P, Soural M. Use of phenacyl thiosalicylates for the preparation of 3-hydroxybenzo[b]thiophene derivatives. Synlett 2018;29:810–4.
  • Pan B, Ren P, Song H, Wang Z. Facile synthesis of 2-substituted benzo[b]thiophen-3-ols in water. Synth Commun 2013;43:1337–44.
  • Chan SLF, Low KH, Yang C, et al. Iron-ligand coordination in tandem radical cyclizations: synthesis of benzo[b]thiophenes by a one-pot reaction of iron 1,3-diketone complexes with 2-thiosalicylic acids. Chem-A Eur J 2011;17:4709–14.
  • Zhou ZZ, Deng YH, Jiang ZH, Chen WH. Microwave-assisted Dieckmann reaction: efficient one-step synthesis of 2-aroylbenzofuran-3-ols. Adv Synth Catal 2010;352:1909–13.
  • Lee JJ, Chang CK, Liu IM, et al. Changes in endogenous monoamines in aged rats. Clin Exp Pharmacol Physiol 2001;28:285–9.
  • Kannan N, Guruvayoorappan C. Protective effect of Bauhinia tomentosa on acetic acid induced ulcerative colitis by regulating antioxidant and inflammatory mediators. Int Immunopharmacol 2013;16:57–66.
  • Nagarjun S, Dhadde SB, Veerapur VP, et al. Ameliorative effect of chromium-D-phenylalanine complex on indomethacin-induced inflammatory bowel disease in rats. Biomed Pharmacother 2017;89:1061–6.
  • Mostert S, Petzer A, Petzer JP. Indanones as high-potency reversible inhibitors of monoamine oxidase. ChemMedChem 2015;10:862–73.
  • Mostert S, Petzer A, Petzer JP. Inhibition of monoamine oxidase by benzoxathiolone analogues. Bioorg Med Chem Lett 2016;26:1200–4.
  • Brunetti L, Michelotto B, Orlando G, et al. Aging increases amyloid β-peptide-induced 8-iso-prostaglandin F2α release from rat brain. Neurobiol Aging 2004;25:125–9.
  • Menghini L, Leporini L, Vecchiotti G, et al. Crocus sativus L. stigmas and byproducts: qualitative fingerprint, antioxidant potentials and enzyme inhibitory activities. Food Res Int 2018;109:91–8.
  • Ferrante C, Orlando G, Recinella L, et al. Central inhibitory effects on feeding induced by the adipo-myokine irisin. Eur J Pharmacol 2016;791:389–94.
  • Charan J, Kantharia N. How to calculate sample size in animal studies? J Pharmacol Pharmacother 2013;4:303.
  • Schrödinger LLC, New York (USA). 2018.
  • Maestro, Schrödinger LLC, New York (USA). 2018.
  • Bochevarov AD, Harder E, Hughes TF, et al. Jaguar: a high-performance quantum chemistry software with strengths in life and materials sciences. Int J Quantum Chem 2013;113:2110–42.
  • Berman HM, Westbrook J, Feng Z, et al. The protein data bank. Nucleic Acids Res 2000;28:235–42.
  • Son SY, Ma J, Kondou Y, et al. 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;105:5739–44.
  • Reis J, Manzella N, Cagide F, et al. Tight-binding inhibition of human monoamine oxidase B by chromone analogs: a kinetic, crystallographic, and biological analysis. J Med Chem 2018;61:4203–12.
  • Glide, Schrödinger LLC, New York (USA). 2018.
  • Carradori S, Ortuso F, Petzer A, et al. Design, synthesis and biochemical evaluation of novel multi-target inhibitors as potential anti-Parkinson agents. Eur J Med Chem 2018;143:1543–52.
  • Chiavaroli A, Recinella L, Ferrante C, et al. Crocus sativus, Serenoa repens and Pinus massoniana extracts modulate inflammatory response in isolated rat prostate challenged with LPS. J Biol Regul Homeost Agents 2017;31:531–41.
  • Locatelli M, Zengin G, Uysal A, et al. Multicomponent pattern and biological activities of seven Asphodeline taxa: potential sources of natural-functional ingredients for bioactive formulations. J Enzyme Inhib Med Chem 2017;32:60–7.
  • Zengin G, Menghini L, Di Sotto A, et al. Chromatographic analyses, in vitro biological activities and cytotoxicity of Cannabis sativa L. essential oil: a multidisciplinary study. Molecules 2018;23:3266.
  • Secci D, Carradori S, Petzer A, et al. 4-(3-Nitrophenyl)thiazol-2-ylhydrazone derivatives as antioxidants and selective hMAO-B inhibitors: synthesis, biological activity and computational analysis. J Enzyme Inhib Med Chem 2019;34:597–612.
  • Mocan A, Diuzheva A, Carradori S, et al. Development of novel techniques to extract phenolic compounds from Romanian cultivars of Prunus domestica L. and their biological properties. Food Chem Toxicol 2018;119:189–98.
  • Van Heesch F, Prins J, Konsman JP, et al. Lipopolysaccharide increases degradation of central monoamines: an in vivo microdialysis study in the nucleus accumbens and medial prefrontal cortex of mice. Eur J Pharmacol 2014;725:55–63.
  • Ferrante C, Recinella L, Locatelli M, et al. Protective effects induced by microwave-assisted aqueous Harpagophytum extract on rat cortex synaptosomes challenged with amyloid β-peptide. Phyther Res 2017;31:1257–64.
  • Ferrante C, Recinella L, Ronci M, et al. Multiple pharmacognostic characterization on hemp commercial cultivars: focus on inflorescence water extract activity. Food Chem Toxicol 2019;125:452–61.
  • Wagmann L, Brandt SD, Kavanagh PV, et al. In vitro monoamine oxidase inhibition potential of alpha-methyltryptamine analog new psychoactive substances for assessing possible toxic risks. Toxicol Lett 2017;272:84–93.
  • Liu YH, Wu WC, Lu YL, et al. Antioxidant and amine oxidase inhibitory activities of hydroxyurea. Biosci Biotechnol Biochem 2010;74:1256–60.
  • Takao K, Toda K, Saito T, Sugita Y. Synthesis of amide and ester derivatives of cinnamic acid and its analogs: evaluation of their free radical scavenging and monoamine oxidase and cholinesterase inhibitory activities. Chem Pharm Bull 2017;65:1020–7.
  • Halliwell B, Clement MV, Ramalingam J, Long LH. Hydrogen peroxide. Ubiquitous in cell culture and in vivo? IUBMB Life 2001;50:251–7.