Synthesis and biological assessment of KojoTacrines as new agents for Alzheimer’s disease therapy

References

• Jameel E, Meena P, Maqbool M. Rational design, synthesis and biological screening of triazine-triazolopyrimidine hybrids as multitarget anti-Alzheimer agents. Eur J Med Chem 2017;136:36–51.
   PubMed Web of Science ®Google Scholar
• Borroni E, Bohrmann B, Grueninger F, et al. Sembragiline: a novel, selective monoamine oxidase type B inhibitor for the treatment of Alzheimer's disease. J Pharmacol Exp Ther 2017;362:413–23.
   PubMed Web of Science ®Google Scholar
• Goedert M, Spillantini MG. A century of Alzheimer's disease. Science 2006;314:777–81.
   PubMed Web of Science ®Google Scholar
• Finder VH. Alzheimer's disease: a general introduction and pathomechanism. J Alzheimers Dis 2010;22:5–19.
   PubMed Web of Science ®Google Scholar
• Savelieff MG, Lee S, Liu Y, Lim MH. Untangling amyloid-β, tau, and metals in Alzheimer's disease. ACS Chem Biol 2013;8:856–65.
   PubMed Web of Science ®Google Scholar
• Bush AI. Drug development based on the metals hypothesis of Alzheimer's disease. J Alzheimers Dis 2008;15:223–40.
   PubMed Web of Science ®Google Scholar
• Opazo C, Huang X, Cherny RA, et al. Metalloenzyme-like activity of Alzheimer's disease beta-amyloid. Cu-dependent catalytic conversion of dopamine, cholesterol, and biological reducing agents to neurotoxic H(2)O(2). J Biol Chem 2002;277:40302–8.
   PubMed Web of Science ®Google Scholar
• Wilkinson D, Wirth Y, Goebel C. Memantine in patients with moderate to severe Alzheimer’s disease: meta-analyses using realistic definitions of response. Dement Geriatr Cogn Disord 2014;37:71–85.
   PubMed Web of Science ®Google Scholar
• Bond M, Rogers G, Peters J, et al. The effectiveness and cost-effectiveness of donepezil, galantamine, rivastigmine and memantine for the treatment of Alzheimer’s disease (review of Technology Appraisal No. 111): a systematic review and economic model. Health Technol Assess 2012;16:1–470. [10.3310/hta16210]
   PubMed Web of Science ®Google Scholar
• Perez D, Martinez A, Gil C, Campillo N. From bitopic inhibitors to multitarget drugs for the future treatment of Alzheimer’s disease. Curr Med Chem 2015;22:3789–806.
   PubMed Web of Science ®Google Scholar
• Agis-Torres A, Sollhuber M, Fernandez M, Sanchez-Montero JM. Multi-target-directed ligands and other therapeutic strategies in the search of a real solution for Alzheimer’s disease. Curr Neuropharmacol 2014;12:2–36.
   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
• León R, Garcia AG, Marco-Contelles J. Recent advances in the multitarget-directed ligands approach for the treatment of Alzheimer's disease. Med Res Rev 2013;33:139–89.
   PubMed Web of Science ®Google Scholar
• Rosini M, Simoni E, Caporaso R, Minarini A. Multitarget strategies in Alzheimer's disease: benefits and challenges on the road to therapeutics. Future Med Chem 2016;8:697–711.
   PubMed 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
• Benchekroun M, Ismaili L, Pudlo M, et al. Donepezil-ferulic acid hybrids as anti-Alzheimer drugs. Future Med Chem 2015;7:15–21.
   PubMed Web of Science ®Google Scholar
• Benchekroun M, Romero A, Egea J, et al. The antioxidant additive approach for Alzheimer’s disease therapy: new ferulic (lipoic) acid plus melatonin modified tacrines as cholinesterases inhibitors, direct antioxidants, and nuclear factor (erythroid-derived 2)-like 2 activators. J Med Chem 2016;59:9967–73.
   PubMed Web of Science ®Google Scholar
• Dgachi Y, Sokolov O, Luzet V, et al. Tetrahydropyranodiquinolin-8-amines as new, non hepatotoxic, antioxidant, and acetylcholinesterase inhibitors for Alzheimer’s disease therapy. Eur J Med Chem 2017;126:576–89.
   PubMed Web of Science ®Google Scholar
• Dgachi Y, Ismaili L, Knez D, et al. Synthesis and biological assessment of racemic benzochromenopyrimidinimines as antioxidant, cholinesterase, and Aβ1 − 42 aggregation inhibitors for Alzheimer’s disease therapy. ChemMedChem 2016;11:1318–27.
   PubMed Web of Science ®Google Scholar
• Watkins PB, Zimmerman HJ, Knapp MJ, et al. HEpatotoxic effects of tacrine administration in patients with Alzheimer's disease. JAMA 1994;271:992–8.
   PubMed Web of Science ®Google Scholar
• Boulebd H, Ismaili L, Martin H, et al. New (benz)imidazolopyridino tacrines as nonhepatotoxic, cholinesterase inhibitors for Alzheimer disease. Future Med Chem 2017;9:723–9.
   PubMed Web of Science ®Google Scholar
• Gomes AJ, Lunardi CN, Gonzalez S, Tedesco AC. The antioxidant action of polypodium leucotomos extract and kojic acid: reactions with reactive oxygen species. Braz J Med Biol Res 2001;34:1487–94.
   PubMed Web of Science ®Google Scholar
• Emami S, Hosseinimehr SJ, Taghdisi SM, Akhlaghpoor S. Kojic acid and its manganese and zinc complexes as potential radioprotective agents. Bioorg Med Chem Lett 2007;17:45–8.
   PubMed Web of Science ®Google Scholar
• Kataev EA, Reddy MR, Reddy GN, et al. Supramolecular catalysis by β-cyclodextrin for the synthesis of kojic acid derivatives in water. New J Chem 2016;40:1693–7.
   Web of Science ®Google Scholar
• Bartolini M, Pistolozzi M, Andrisano V, et al. Chemical and pharmacological studies on enantiomerically pure p-methoxytacripyrines, promising multi-target-directed ligands for the treatment of Alzheimer’s disease. ChemMedChem 2011;6:1990–7.
   PubMed Web of Science ®Google Scholar
• Denizot F, Lang R. Rapid colorimetric assay for cell growth and survival. Modifications to the tetrazolium dye procedure giving improved sensitivity and reliability. J Immunol Methods 1986;89:271–7.
   PubMed Web of Science ®Google Scholar
• Decker M. Homobivalent quinazolinimines as novel nanomolar inhibitors of cholinesterases with dirigible selectivity toward butyrylcholinesterase. J Med Chem 2006;49:5411–3.
   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
• Benchekroun M, Bartolini M, Egea J, et al. Novel tacrine-grafted Ugi adducts as multipotent anti-Alzheimer drugs: a synthetic renewal in tacrine-ferulic acid hybrids. ChemMedChem 2015;10:523–39.
   PubMed Web of Science ®Google Scholar
• Dávalos A, Gómez-Cordovés C, Bartolomé B. Extending applicability of the oxygen radical absorbance capacity (ORAC-fluorescein) assay. J Agric Food Chem 2004;52:48–54.
   PubMed Web of Science ®Google Scholar
• Dgachi Y, Bautista-Aguilera OM, Benchekroun M, et al. Synthesis and biological evaluation of benzochromenopyrimidinones as cholinesterase inhibitors and potent antioxidant, non-hepatotoxic agents for Alzheimer’s disease. Molecules 2016;21:634.
   PubMed Web of Science ®Google Scholar
• Trott O, Olson AJ. AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. J Comput Chem 2010;31:455–61.
   PubMed Web of Science ®Google Scholar
• Brooks BR, Bruccoleri RE, Olafson BD, et al. CHARMM: a program for macromolecular energy, minimization, and dynamics calculations. J Comput Chem 1983;4:187–217.
   Web of Science ®Google Scholar
• Piao M-Z, Imafuku K. Convenient synthesis of amino-substituted pyranopyranones. Tetrahedron Lett 1997;38:5301–2.
   Web of Science ®Google Scholar
• Marco-Contelles J, Pérez-Mayoral E, Samadi A, et al. Recent advances in the Friedländer reaction. Chem Rev 2009;109:2652–71.
   PubMed Web of Science ®Google Scholar
• Ou B, Hampsch-Woodill M, Prior RL. Development and validation of an improved oxygen radical absorbance capacity assay using fluorescein as the fluorescent probe. J Agric Food Chem 2001;49:4619–26.
   PubMed Web of Science ®Google Scholar
• Fang L, Kraus B, Lehmann J, et al. Design and synthesis of tacrine-ferulic acid hybrids as multi-potent anti-Alzheimer drug candidates. Bioorg Med Chem Lett 2008;18:2905–9.
   PubMed Web of Science ®Google Scholar
• Shi C, Zhao L, Zhu B, et al. Protective effects of Ginkgo biloba extract (EGb761) and its constituents quercetin and ginkgolide B against beta-amyloid peptide-induced toxicity in SH-SY5Y cells. Chem Biol Interact 2009;181:115–23.
   PubMed Web of Science ®Google Scholar
• González-Muñoz GC, Arce MP, López B, et al. N-Acylaminophenothiazines: neuroprotective agents displaying multifunctional activities for a potential treatment of Alzheimer's disease. Eur J Med Chem 2011;46:2224–35.
   PubMed Web of Science ®Google Scholar
• Martins C, Carreiras MC, León R, et al. Synthesis and biological assessment of diversely substituted furo[2,3-b]quinolin-4-amine and pyrrolo[2,3-b]quinolin-4-amine derivatives, as novel tacrine analogues. Eur J Med Chem 2011;46:6119–30.
   PubMed Web of Science ®Google Scholar