Development of naringenin-O-alkylamine derivatives as multifunctional agents for the treatment of Alzheimer’s disease

References

• World Alzheimer Report 2019: Attitudes to Dementia, Alzheimer’s Disease International; 2019, pp. 1–13.
   Google Scholar
• Jagust W. Imaging the evolution and pathophysiology of Alzheimer disease. Nat Rev Neurosci 2018;19:687–700.
   PubMed Web of Science ®Google Scholar
• Anand P, Singh B. A review on cholinesterase inhibitors for Alzheimer's disease. Arch Pharm Res 2013;36:375–99.
   PubMed Web of Science ®Google Scholar
• Hebscher M, Voss JL. Testing network properties of episodic memory using non-invasive brain stimulation. Curr Opin Behav Sci 2020;32:35–42.
   PubMed Web of Science ®Google Scholar
• Alvarez A, Opazo C, Alarcón R, et al. Acetylcholinesterase promotes the aggregation of amyloid-beta-peptide fragments by forming a complex with the growing fibrils. J Mol Biol 1997;272:348–61.
   PubMed Web of Science ®Google Scholar
• Hardy J, Selkoe DJ. The amyloid hypothesis of Alzheimer's disease: progress and problems on the road to therapeutics. Science 2002;297: 353–6.
   PubMed Web of Science ®Google Scholar
• Calsolaro V, Edison P. Neuroinflammation in Alzheimer's disease: current evidence and future directions. Alzheimers Dement 2016;12:719–32.
   PubMed Web of Science ®Google Scholar
• Cheignon C, Tomas M, Bonnefont-Rousselot D, et al. Oxidative stress and the amyloid beta peptide in Alzheimer's disease. Redox Biol 2018;14:450–64.
   PubMed Web of Science ®Google Scholar
• Lane DJR, Ayton S, Bush AI. Iron and Alzheimer's disease: an update on emerging mechanisms. J Alzheimers Dis 2018;64:S379–S395.
   PubMed Web of Science ®Google Scholar
• Cavalli A, Bolognesi ML, Minarini A, et al. Multi-target-directed ligands to combat neurodegenerative diseases. J Med Chem 2008;51:347–72.
   PubMed Web of Science ®Google Scholar
• Zhang P, Xu S, Zhu Z, Xu J. Multi-target design strategies for the improved treatment of Alzheimer's disease. Eur J Med Chem 2019;176:228–47.
   PubMed Web of Science ®Google Scholar
• de Freitas Silva M, Dias KST, Gontijo VS, et al. Multi-target directed drugs as a modern approach for drug design towards Alzheimer's disease: an update. Curr Med Chem 2018;25:3491–525.
   PubMed Web of Science ®Google Scholar
• Huang W, Liang M, Li Q, et al. Development of the "hidden" multifunctional agents for Alzheimer's disease. Eur J Med Chem 2019;177:247–58.
   PubMed Web of Science ®Google Scholar
• Joshi R, Kulkarni YA, Wairkar S. Pharmacokinetic, pharmacodynamic and formulations aspects of Naringenin: an update. Life Sci 2018;215:43–56.
   PubMed Web of Science ®Google Scholar
• Ghofrani S, Joghataei MT, Mohseni S, et al. Naringenin improves learning and memory in an Alzheimer's disease rat model: insights into the underlying mechanisms. Eur J Pharmacol 2015;764:195–201.
   PubMed Web of Science ®Google Scholar
• Wu J, Kou X, Ju H, et al. Design, synthesis and biological evaluation of naringenin carbamate derivatives as potential multifunctional agents for the treatment of Alzheimer's disease. Bioorg Med Chem Lett 2021;49:128316.
   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
• Bai P, Wang K, Zhang P, et al. Development of chalcone-O-alkylamine derivatives as multifunctional agents against Alzheimer's disease. Eur J Med Chem 2019;183:111737.
   PubMed Web of Science ®Google Scholar
• Qiang X, Sang Z, Yuan W, et al. Design, synthesis and evaluation of genistein-O-alkylbenzylamines as potential multifunctional agents for the treatment of Alzheimer's disease. Eur J Med Chem 2014;76:314–31.
   PubMed Web of Science ®Google Scholar
• Sang Z, Wang K, Shi J, et al. The development of advanced structural framework as multi-target-directed ligands for the treatment of Alzheimer's disease. Eur J Med Chem 2020;192:112180.
   PubMed Web of Science ®Google Scholar
• Li HQ, Shi L, Li QS, Liu PG, et al. Synthesis of C(7) modified chrysin derivatives designing to inhibit beta-ketoacyl-acyl carrier protein synthase III (FabH) as antibiotics. Bioorg Med Chem 2009;17:6264–9.
   PubMed Web of Science ®Google Scholar
• Sang Z, Wang K, Shi J, et al. Apigenin-rivastigmine hybrids as multi-target-directed liagnds for the treatment of Alzheimer's disease. Eur J Med Chem 2020;187:111958.
   PubMed Web of Science ®Google Scholar
• Košak U, Brus B, Knez D, et al. The magic of crystal structure-based inhibitor optimization: development of a butyrylcholinesterase inhibitor with picomolar affinity and in vivo activity. J Med Chem 2018;61:119–39.
   PubMed Web of Science ®Google Scholar
• Wang LL, Du Y, Li SM, et al. Design, synthesis and evaluation of tetrahydrocarbazole derivatives as potential hypoglycemic agents. Bioorg Chem 2021;115:105172.
   PubMed Web of Science ®Google Scholar
• Sharma P, Tripathi A, Tripathi PN, et al. Design and development of multitarget-directed N-Benzylpiperidine analogs as potential candidates for the treatment of Alzheimer's disease. Eur J Med Chem 2019;167:510–24.
   PubMed Web of Science ®Google Scholar
• Tripathi A, Choubey PK, Sharma P, et al. Design and development of molecular hybrids of 2-pyridylpiperazine and 5-phenyl-1,3,4-oxadiazoles as potential multifunctional agents to treat Alzheimer's disease. Eur J Med Chem 2019;183:111707.
   PubMed Web of Science ®Google Scholar
• Tripathi PN, Srivastava P, Sharma P, et al. Biphenyl-3-oxo-1,2,4-triazine linked piperazine derivatives as potential cholinesterase inhibitors with anti-oxidant property to improve the learning and memory. Bioorg Chem 2019;85:82–96.
   PubMed Web of Science ®Google Scholar
• Sang Z, Wang K, Han X, et al. Design, synthesis, and evaluation of novel ferulic acid derivatives as multi-target-directed ligands for the treatment of Alzheimer's disease. ACS Chem Neurosci 2019;10:1008–24.
   PubMed Web of Science ®Google Scholar
• Li Y, Qiang X, Li Y, et al. Pterostilbene-O-acetamidoalkylbenzylamines derivatives as novel dual inhibitors of cholinesterase with anti-β-amyloid aggregation and antioxidant properties for the treatment of Alzheimer's disease. Bioorg Med Chem Lett 2016;26:2035–9.
   PubMed Web of Science ®Google Scholar
• Di L, Kerns EH, Fan K, et al. High throughput artificial membrane permeability assay for blood-brain barrier. Eur J Med Chem 2003;38:223–32.
   PubMed Web of Science ®Google Scholar
• Sang Z, Wang K, Bai P, et al. Design, synthesis and biological evaluation of novel O-carbamoyl ferulamide derivatives as multi-target-directed ligands for the treatment of Alzheimer's disease. Eur J Med Chem 2020;194:112265.
   PubMed Web of Science ®Google Scholar
• Tian C, Qiang X, Song Q, et al. Flurbiprofen-chalcone hybrid Mannich base derivatives as balanced multifunctional agents against Alzheimer's disease: design, synthesis and biological evaluation. Bioorg Chem 2020;94:103477.
   PubMed Web of Science ®Google Scholar
• Yang Z, Song Q, Cao Z, et al. Design, synthesis and evaluation of flurbiprofen-clioquinol hybrids as multitarget-directed ligands against Alzheimer's disease. Bioorg Med Chem 2020;28:115374.
   PubMed Web of Science ®Google Scholar
• http://www.molinspiration.com/cgi-bin/properties
   Google Scholar