Design of enamides as new selective monoamine oxidase-B inhibitors.
Alzheimer Disease
/ drug therapy
Amines
/ chemistry
Binding, Competitive
Cinnamates
/ chemistry
Drug Design
Drug Discovery
Humans
Hydrogen Bonding
Molecular Docking Simulation
/ methods
Molecular Structure
Monoamine Oxidase
/ metabolism
Monoamine Oxidase Inhibitors
/ chemistry
Parkinson Disease
/ drug therapy
Structure-Activity Relationship
MAO-B inhibitors
docking simulations
enamides
kinetics
reversibilities
Journal
The Journal of pharmacy and pharmacology
ISSN: 2042-7158
Titre abrégé: J Pharm Pharmacol
Pays: England
ID NLM: 0376363
Informations de publication
Date de publication:
Jul 2020
Jul 2020
Historique:
received:
30
09
2019
accepted:
08
03
2020
pubmed:
5
4
2020
medline:
30
3
2021
entrez:
5
4
2020
Statut:
ppublish
Résumé
To develop of new class of selective and reversible MAO-B inhibitors from enamides. Syntheses of the titled derivatives (AD1-AD11) were achieved by reacting cinnamoyl chloride and various primary and secondary amines in basic medium. All eleven compounds were investigated for in vitro inhibitory activities against recombinant human MAO-A and MAO-B. The reversibilities of lead compound inhibitions were analysed by dialysis. MTT assays of lead compounds were performed using normal VERO cell lines. Compounds AD3 and AD9 exhibited the greatest inhibitory activity against MAO-B with IC These results encourage further studies on the enamide scaffold as potential drug candidates for the treatment of Alzheimer's and Parkinson's diseases.
Substances chimiques
Amines
0
Cinnamates
0
Monoamine Oxidase Inhibitors
0
cinnamoyl chloride
04L46S032W
Monoamine Oxidase
EC 1.4.3.4
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
916-926Informations de copyright
© 2020 Royal Pharmaceutical Society.
Références
Wouters J. Structural aspects of monoamine oxidase and its reversible inhibition. Curr Med Chem 1998; 5: 137-162.
Ramsay RR. Inhibitor design for monoamine oxidases. Curr Pharm Des 2013; 19: 2529-2539.
Mathew B et al. Monoamine oxidase inhibitors: perspective design for the treatment of depression and neurological disorders. Curr Enzyme Inhib 2016; 12: 115-122.
Bolasco A et al. Focusing on new monoamine oxidase inhibitors. Expert Opin Ther Pat 2010; 20: 909-939.
Tripathi RKP, Ayyannan SR. Monoamine oxidase-B inhibitors as potential neurotherapeutic agents: an overview and update. Med Res Rev 2019; 39: 1603-1706.
Kumar B et al. A perspective on monoamine oxidase enzyme as drug target. Challenges and opportunities. Curr Drug Targets 2017; 18: 87-97.
Carradori S, Petzer JP. Novel monoamine oxidase inhibitors: a patent review (2012-2014). Expert Opin Ther Pat 2015; 25: 91-110.
Mathew B et al. Refining the structural features of chromones as selective MAO-B inhibitors: exploration of combined pharmacophore-based 3D-QSAR and quantum chemical studies. ChemistrySelect 2017; 2: 11645-11652.
Knez D et al. Dual inhibitors of cholinesterases and monoamine oxidases for Alzheimer's disease. Future Med Chem 2017; 9: 811-832.
Scholl M et al. Early astrocytes in autosomal dominant Alzheimer's disease measured in vivo by multi-trace positron emission tomography. Sci Rep 2015; 5: 16404.
Pazini AM et al. Selegiline reverses aβ25-35-induced cognitive deficit in male mice. Neurochem Res 2013; 38: 87-97.
Schedin-Weiss S et al. Monoamine oxidase B is elevated in Alzheimer disease neurons, is associated with the γ-secretase and regulates neuronal amloyd β-peptide levels. Alzheimers Res Ther 2017; 9: 57.
Mathew B et al. Emerging therapeutic potentials of dual-acting MAO and AChE inhibitors in Alzheimer's and Parkinson's diseases. Arch Pharm (Weinheim) 2019; 352: e1900177.
Harilal S et al. Advancements in nanotherapeutics for Alzheimer's disease: current perspectives. J Pharm Pharmacol 2019; 71: 1370-1381.
Rodriguez-Oroz MC et al. Initial clinical manifestations of Parkinson's disease: features and pathophysiological mechanisms. Lancet Neurol 2009; 8: 1128-1139.
Zhou ZD et al. The therapeutic implications of tea polyphenols against dopamine (DA) neuron degeneration in Parkinson's disease (PD). Cells 2019; 8: 911.
Schapira AHV et al. Novel pharmacological targets for the treatment of Parkinson's disease. Nat Rev Drug Discov 2006; 5: 845-854.
D'Amato R et al. Selectivity of the Parkinsonian neurotoxin MPTP: toxic metabolite MPP+ binds to neuromelanin. Science 1986; 231: 987-989.
Carradori S et al. MAO inhibitors and their wider applications: a patent review. Expert Opin Ther Pat 2018; 28: 211-226.
Joy M et al. Structural features of Safinamide: a combined Hirshfeld surface analysis & quantum chemical treatment. Chem Data Coll 2018; 17-16: 404-4014.
Mathew B et al. Monoamine oxidase inhibitory actions of chalcones. A mini review. Cent Nerv Syst Agents Med Chem 2016; 16: 120-136.
Mathew B. Unraveling the structural requirements of chalcone chemistry towards monoamine oxidase inhibition. Cent Nerv Syst Agents Med Chem 2019; 19: 6-7.
Mathew B et al. Development of fluorinated methoxylated chalcones as selective monoamine oxidase-B inhibitors: synthesis, biochemistry and molecular docking studies. Bioorg Chem 2015; 62: 22-29.
Mathew B et al. Synthesis, biochemistry, and computational studies of brominated thienyl chalcones: a new class of reversible MAO-B inhibitors. ChemMedChem 2016; 11: 1161-1171.
Mathew B et al. Monoamine oxidase inhibitory activity: methyl- versus chloro-chalcone derivatives. ChemMedChem 2016; 11: 2649-2655.
Sasidharan R et al. Identification of indole based chalcones: discovery of potent, selective and reversible class of MAO-B inhibitors. Arch Pharm Chem Life Sci 2016; 349: 627-637.
Mathew B et al. Characterization of thienylchalcones as hMAO-B inhibitors: synthesis, biochemistry and molecular dynamics studies. ChemistrySelect 2017; 2: 11113-11119.
Mathew B et al. Potent and highly selective dual-targeting monoamine oxidase-B inhibitors: fluorinated chalcones of morpholine versus imidazole. Arch Pharm (Weinheim) 2019; 352(4): e1800309.
Mathew B et al. Structural exploration of synthetic chromones as selective MAO-B inhibitors. Comb Chem High Throughput Screen 2017; 20: 522-532.
Gaspar A et al. Chromone, a privileged scaffold for the development of monoamine oxidase inhibition. J Med Chem 2011; 54: 5165-5173.
Matos MJ et al. Focusing on new monoamine oxidase inhibitors: Differently substituted coumarins as an interesting scaffold. Curr Top Med Chem 2012; 12: 2210-2230.
Mathew B et al. Pyrazoline. A promising scaffold for the inhibition of monoamine oxidase. Cent Nerv Syst Agents Med Chem 2013; 13: 195-206.
Secci D et al. Discovery and optimization of pyrazoline derivatives as promising monoamine oxidase inhibitors. Curr Top Med Chem 2012; 12: 2240-2257.
Mei-Xiang W et al. Exploring tertiary amides as versatile synthons in organic synthesis. Chem Commun (Camb) 2015; 51: 6039-6044.
Carbery DR. Enamides: valuable organic substrates. Org Biomol Chem 2008; 6: 3455-3460.
Gunia-Krzyz A. Anticonvulsant activity, crystal structures, and preliminary safety evaluation of N-trans-cinnamoyl derivatives of selected (un)modified aminoalkanols. Eur J Med Chem 2016; 107: 26-37.
Mathew B et al. Pharmacophore based 3D-QSAR analysis of thienyl chalcone as new class of human MAO-B inhibitors. Investigation of combined quantum chemical and molecular dynamics approach. J Phys Chem B 2017; 121: 1186-1203.
Legoabe L et al. Monoamine oxidase inhibition by selected anilide derivatives. Eur J Med Chem 2011; 46: 5162-5174.
Mu LH et al. Synthesis and inhibitory effect of piperine derivatives on monoamine oxidases. Bioorg Med Chem Lett 2022; 22: 3343-3348.
Mathew B et al. Selected aryl thiosemicarbazones as a new class of multi-targeted monoamine oxidase inhibitors. Med Chem Comm 2018; 9: 871-1881.
Lakshminarayanan B et al. Ethoxylated head of chalcones as a new class of multi-targeted MAO inhibitors. ChemistrySelect 2019; 4: 6614-6619.
Lee HW et al. Potent selective monoamine oxidase B inhibition by maackiain, a pterocarpan from the roots of Sophora flavescens. Bioorg Med Chem Lett 2016; 26: 4714-4719.
Baek SC et al. Selective inhibition of monoamine oxidase A by hispidol. Bioorg Med Chem Lett 2018; 28: 584-588.
Sasidharan R et al. Imidazole bearing chalcones as new class of monoamine oxidase inhibitors. Biomed Pharmacother 2018; 106: 8-13.
Kurokawa M et al. Activation of cellular immunity in herpes simplex virus type 1- infected mice by the oral administration of aqueous extract of Moringa oleifera Lam. leaves. Phytother Res 2016; 30: 797-804.
Son SY et al. 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.
Binda C et al. Structures of human monoamine oxidase B complexes with selective noncovalent inhibitors: safinamide and coumarin analogs. J Med Chem 2007; 50: 5848-5852.
Schrödinger Release 2018-2. Schrödinger Suite 2018-2 Protein Preparation Wizard. New York, NY: LLC, 2018.
LigPrep. Schrödinger. New York, NY: LLC, 2018.
Schrödinger Release 2018-2. Schrödinger Suite 2018-2 QM-Polarized Ligand Docking Protocol. New York, NY: LLC, 2018.
Mangiatordi GF et al. A rational approach to elucidate human monoamine oxidase molecular selectivity of coumarin-based inhibitors. Eur J Pharm Sci 2017; 101: 90-99.
Genheden S, Ryde Y. The MM/PBSA and MM/GBSA methods to estimate ligand-binding affinities. Expert Opin Drug Discov 2015; 10: 449-461.
Prime. Schrödinger. New York, NY: LLC, 2018.
Parambi DGT et al. Design, synthesis and biological evaluation of oxygenated chalcones as potent and selective MAO-B inhibitors. Bioorg Chem 2019; 93: 103335.
Farina R et al. Structure-based design and optimization of multitarget-directed 2H-chromen-2-one derivatives as potent inhibitors of monoamine oxidase B and cholinesterases. J Med Chem 2015; 58: 5561-5578.
Mathew B et al. Exploration of chlorinated thienyl chalcones: A new class of monoamine oxidase-B inhibitors. Int J Bio Macromol 2016; 91: 680-695.
Mathew B et al. Monoamine oxidase inhibitory activities of methoxy substituted chalcones. Int J Bio Macromol 2017; 104: 1321-1329.
Suresh J et al. Discovery of potent and reversible MAO-B inhibitors as furanochalcones. Int J Bio Macromol 2018; 108: 660-664.
Pisani L et al. Targeting monoamine oxidases with multipotent ligands: An emerging strategy in the search of new drugs against neurodegenerative diseases. Curr Med Chem 2011; 18: 4568-4587.
Pisani L et al. Searching for multi-targeting neurotherpeutics against Alzheimer's. Discovery of potent AChE-MAO-B inhibitors through the decoration of 2H-chromen-2-one structural motif. Molecules 2016; 21: 3-15.