Discovery of novel isoflavone derivatives as AChE/BuChE dual-targeted inhibitors: synthesis, biological evaluation and molecular modelling

References

• Kumar A, Singh A. A review on Alzheimer's disease pathophysiology and its management: an update. Pharmacol Rep 2015;67:195–203.
   PubMed Web of Science ®Google Scholar
• Anand R, Gill KD, Mahdi AA. Therapeutics of Alzheimer's disease: past, present and future. Neuropharmacology 2014;76 Pt A:27–50.
   PubMed Web of Science ®Google Scholar
• Geula C, Mesulam MM. Cholinesterases and the pathology of Alzheimer disease. Alzheimer Dis Assoc Disord 1995;9 Suppl 2:23–8.
   PubMed Web of Science ®Google Scholar
• Overk CR, Felder CC, Tu Y, et al. Cortical M1 receptor concentration increases without a concomitant change in function in Alzheimer's disease. J Chem Neuroanat 2010;40:63–70.
   PubMed Web of Science ®Google Scholar
• Yu Q-S, Holloway HW, Flippen-Anderson JL, et al. Methyl analogues of the experimental alzheimer drug phenserine: synthesis and structure/activity relationships for acetyl- and butyrylcholinesterase inhibitory action. J Med Chem 2001;44:4062–71.
   PubMed Web of Science ®Google Scholar
• Silva T, Reis J, Teixeira J, Borges JF. Alzheimer's disease, enzyme targets and drug discovery struggles: from natural products to drug prototypes. Ageing Res Rev 2014;15:116–45.
   PubMed Web of Science ®Google Scholar
• Pepeu G, Giovannini MG. Cholinesterase inhibitors and memory. Chem Biol Interact 2010;187:403–8.
   PubMed Web of Science ®Google Scholar
• AnandSingh PB. A review on cholinesterase inhibitors for Alzheimer's disease. Arch Pharm Res 2013;36:375–99.
   PubMed Web of Science ®Google Scholar
• Houghton PJ, Ren Y, Howes MJ. Acetylcholinesterase inhibitors from plants and fungi. Nat Prod Rep 2006;23:181–99.
   PubMed Web of Science ®Google Scholar
• Munoz FJ, Inestrosa NC. Neurotoxicity of acetylcholinesterase amyloid beta-peptide aggregates is dependent on the type of abeta peptide and the ache concentration present in the complexes. FEBS Lett. 1999;450:205–9.
   PubMed Web of Science ®Google Scholar
• Sugimoto H. Donepezil hydrochloride: a treatment drug for Alzheimer's disease. Chem Rec 2001; 1: 63–73.
   PubMed Web of Science ®Google Scholar
• Zarotsky V, Sramek JJ, Cutler NR. Galantamine hydrobromide: an agent for Alzheimer's disease. Am J Health Syst Pharm 2003;60:446–52.
   PubMed Web of Science ®Google Scholar
• CastroMartinez AA. Targeting beta-amyloid pathogenesis through acetylcholinesterase inhibitors. Curr Pharm Des 2006;12:4377–87.
   PubMed Web of Science ®Google Scholar
• Birks J. Cholinesterase inhibitors for Alzheimer's disease. Cochrane Database Syst Rev 2006;1:CD005593.
   Web of Science ®Google Scholar
• Darvesh S, Hopkins D, Geula AC. Neurobiology of butyrylcholinesterase. Nat Rev Neurosci 2003;4:131–8.
   PubMed Web of Science ®Google Scholar
• Greig NH, Utsuki T, Yu Q-S, et al. A new therapeutic target in Alzheimer's disease treatment: attention to butyrylcholinesterase. Curr Med Res Opin 2001;17:159–65.
   PubMed Web of Science ®Google Scholar
• Recanatini M, Cavalli A. Acetylcholinesterase inhibitors in the context of therapeutic strategies to combat Alzheimer’s disease. Expert Opin Ther Pat 2005;12:1853–65.
   Web of Science ®Google Scholar
• Ismaili L, Refouvelet B, Benchekroun M, et al. Multitarget compounds bearing tacrine- and donepezil-like structural and functional motifs for the potential treatment of Alzheimer's disease. Prog Neurobiol 2017;151:4–34.
   PubMed Web of Science ®Google Scholar
• Guzior N, Wieckowska A, Panek D, Malawska DB. Recent development of multifunctional agents as potential drug candidates for the treatment of Alzheimer’s disease. Curr Med Chem 2015;22:373–404.
   PubMed Web of Science ®Google Scholar
• Bacalhau P, San Juan AA, Goth A, et al. Insights into (S)-rivastigmine inhibition of butyrylcholinesterase (Buche): molecular docking and saturation transfer difference NMR (STD-NMR). Bioorg Chem 2016; 67:105–9.
   PubMed Web of Science ®Google Scholar
• Singh M, Silakari O. Design, synthesis and biological evaluation of novel 2-phenyl-1-benzopyran-4-one derivatives as potential poly-functional anti-Alzheimer's agents. RSC Adv 2016;6:108411–22.
   Web of Science ®Google Scholar
• Li SY, Wang XB, Xie SS, et al. Multifunctional tacrine-flavonoid hybrids with cholinergic, beta-amyloid-reducing, and metal chelating properties for the treatment of Alzheimer's disease. Eur J Med Chem 2013;69:632–46.
   PubMed Web of Science ®Google Scholar
• Sun Y, Chen J, Chen X, et al. Inhibition of cholinesterase and monoamine oxidase-B activity by tacrine-homoisoflavonoid hybrids. Bioorg Med Chem 2013;21:7406–17.
   PubMed Web of Science ®Google Scholar
• Desideri N, Bolasco A, Fioravanti R, et al. Homoisoflavonoids: natural scaffolds with potent and selective monoamine oxidase-B inhibition properties. J Med Chem 2011;54:2155–64.
   PubMed Web of Science ®Google Scholar
• Liao S, Deng H, Huang S, et al. Design, synthesis and evaluation of novel 5,6,7-trimethoxyflavone-6-chlorotacrine hybrids as potential multifunctional agents for the treatment of Alzheimer's disease. Bioorg Med Chem Lett 2015;25:1541–5.
   PubMed Web of Science ®Google Scholar
• Sang Z, Qiang X, Li Y, et al. Design, synthesis and evaluation of scutellarein-O-alkylamines as multifunctional agents for the treatment of Alzheimer's disease. Eur J Med Chem 2015;94:348–66.
   PubMed Web of Science ®Google Scholar
• Ellman GL, Courtney KD, Andres V, Featherstone RM. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol 1961;7:88–95.
   PubMed Web of Science ®Google Scholar
• Kim DH, Hung TM, Bae KH, et al. Gomisin A improves scopolamine-induced memory impairment in mice. Eur J Pharmacol 2006; 542: 129–35.
   PubMed Web of Science ®Google Scholar
• Lima JA, Costa RS, Epifanio RA, et al. Geissospermum vellosii stembark: anticholinesterase activity and improvement of scopolamine-induced memory deficits. Pharmacol Biochem Behav 2009;92:508–13.
   PubMed Web of Science ®Google Scholar
• Kurt BZ, Gazioglu I, Basile L, et al. Potential of aryl-urea-benzofuranylthiazoles hybrids as multitasking agents in Alzheimer's disease. Eur J Med Chem 2015;102:80–92.
   PubMed Web of Science ®Google Scholar
• Bourne Y, Sharpless KB, Taylor P, Marchot PP. Steric and dynamic parameters influencing in situ cycloadditions to form triazole inhibitors with crystalline acetylcholinesterase. J Am Chem Soc 2016;138:1611–21.
   PubMed Web of Science ®Google Scholar
• Nachon F, Carletti E, Ronco C, et al. Crystal structures of human cholinesterases in complex with huprine w and tacrine: elements of specificity for anti-Alzheimer's drugs targeting acetyl- and butyryl-cholinesterase. Biochem J 2013;453:393–9.
   PubMed Web of Science ®Google Scholar
• Delcanale M, Amari G, Armani E, et al. Novel basic isoflavones as inhibitors of bone resorption. Helv Chim Acta 2001;84:2417–29.
   Web of Science ®Google Scholar
• Seguin H, Gardette D, Moreau M-F, et al. A general method for the synthesis of N, N-dialkylaminobutylamines. Synth Commun 1998;28:4257–72.
   Web of Science ®Google Scholar
• Overk CR, Felder CC, Tu Y, et al. Cortical M1 receptor concentration increases without a concomitant change in function in Alzheimer’s disease. J Chem Neuroanat 2010;40:63–70.
   PubMed Web of Science ®Google Scholar
• Inesi A, Mucciante L, Rossi VL. A convenient method for the synthesis of carbamate esters from amines and tetraethylammonium hydrogen carbonate. J Organ Chem 1998;63:1337–8.
   Web of Science ®Google Scholar