1,641
Views
19
CrossRef citations to date
0
Altmetric
Research Article

Design, synthesis and biological activity of 1H-indene-2-carboxamides as multi-targeted anti-Alzheimer agents

, , , , , , & show all
Pages 13-23 | Received 03 Mar 2016, Accepted 30 Mar 2016, Published online: 26 May 2016

References

  • Hardy J, Bogdanovic N, Winblad B, et al. Pathways to Alzheimer's disease. J Intern Med 2014;275:296–303
  • Samadi A, Estrada M, Pérez C, et al. Pyridonepezils, new dual AChE inhibitors as potential drugs for the treatment of Alzheimer’s disease: synthesis, biological assessment, and molecular modeling. Eur J Med Chem 2012;57:296–301
  • Sugimoto H, Ogura H, Arai Y, et al. Research and development of donepezil hydrochloride, a new type of acetylcholinesterase inhibitor. Jpn J Pharmacol 2002;89:7–20
  • Akasofu S, Kimura M, Kosasa I, et al. Study of neuroprotection of donepezil, a therapy for Alzheimer’s disease. Chem Biol Interact 2008;175:222–6
  • Dumas JA, Newhouse PA. The cholinergic hypothesis of cognitive aging revisited again: cholinergic functional compensation. Pharmacol Biochem Behav 2011;99:254–61
  • Tai HC, Serrano-Pozo A, Hashimoto T, et al. The synaptic accumulation of hyperphosphorylated tau oligomers in Alzheimer disease is associated with dysfunction of the ubiquitin-proteasome system. Am J Pathol 2012;181:1426–35
  • Li B, Stribley JA, Ticu A, et al. Abundant tissue butyrylcholinesterase and its possible function in the acetylcholinesterase knockout mouse. J Neurochem 2000;75:1320–31
  • Mesulam MM, Guillozet A, Show P, et al. Acetylcholinesterase knockouts establish central cholinergic pathways and can use butyrylcholinesterase to hydrolyze acetylcholine. Neuroscience 2002;110:627–39
  • Darvesh S, Hopkins DA, Geula C. Neurobiology of butyrylcholinesterase. Nat Rev Neurosci 2003;4:131–8
  • Fernández-Bachiller MI, Pérez C, González-Muñoz GC, et al. Novel tacrine-8-hydroxyquinoline hybrids as multifunctional agents for the treatment of Alzheimer's disease, with neuroprotective, cholinergic, antioxidant, and copper-complexing properties. J Med Chem 2010;53:4927–37
  • Galdeano C, Viayna E, Arroyo P, et al. Structural determinants of the multifunctional profile of dual binding site acetylcholinesterase inhibitors as anti-Alzheimer agents. Curr Pharm Des 2010;16:2816–36
  • Yankner BA, Dawes LR, Fisher S, et al. Neurotoxicity of a fragment of the amyloid precursor associated with Alzheimer's disease. Science 1989;245:417–20
  • He Y, Yao PF, Chen SB, et al. Synthesis and evaluation of 7,8-dehydrorutaecarpine derivatives as potential multifunctional agents for the treatment of Alzheimer's disease. Eur J Med Chem 2013;63:299–312
  • Bush AI. Drug development based on the metals hypothesis of Alzheimer's disease. J Alzheimers Dis 2008;15:223–40
  • Dong J, Atwood CS, Anderson VE, et al. Metal binding and oxidation of amyloid-beta within isolated senile plaque cores: Raman microscopic evidence. Biochemistry 2003;42:2768–73
  • 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
  • Hansen RA, Gartlehner G, Webb AP, et al. Efficacy and safety of donepezil, galantamine, and rivastigmine for the treatment of Alzheimer's disease: a systematic review and meta-analysis. Clin Interv Aging 2008;3:211–25
  • FDA Approves Expanded Use of Treatment for Patients with Severe Alzheimer's Disease [press release]. U.S. Food and Drug Administration; 2006
  • Kasap Z, Yerdelen KO, Koca M, Anil B. Synthesis, docking, metal chelating and biological activity of new oxalamide analogues for Alzheimer disease. Lat Am J Pharm 2015;34:924–33
  • Koca M, Yerdelen KO, Anil B, Kasap Z. Microwave assisted synthesis, molecular docking, and cholinesterase inhibitory activities of new ethanediamide and 2-butenediamide analogues. Chem Pharm Bull 2015;63:210–17
  • Yerdelen KO, Gul HI. Synthesis and anticholinesterase activity of fumaramide derivatives. Med Chem Res 2013;22:4920–9
  • Yerdelen KO, Koca M, Kasap Z, Anil B. Preparation, anticholinesterase activity, and docking study of new 2-butenediamide and oxalamide derivatives. J Enzyme Inhib Med Chem 2015;30:671–8
  • Yerdelen KO, Tosun E. Synthesis, docking and biological evaluation of oxamide and fumaramide analogs as potential AChE and BuChE inhibitors. Med Chem Res 2015;24:588–602
  • Fukushi H, Mabuchi H, Itoh K, et al. Synthesis and platelet-activating factor (PAF)-antagonistic activities of 1,4-disubstituted piperazine derivatives. Chem Pharm Bull 1994;42:541–50
  • Ellman GL, Courtney D, Andies V, Featherstone RM. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol 1961;7:88–95
  • Rosini M, Simoni E, Bartolini M, et al. Inhibition of acetylcholinesterase, beta-amyloid aggregation, and NMDA receptors in Alzheimer's disease: a promising direction for the multi-target-directed ligands gold rush. J Med Chem 2008;51:4381–4
  • Yang F, Lim GP, Begum AN, et al. Curcumin inhibits formation of amyloid beta oligomers and fibrils, binds plaques, and reduces amyloid in vivo. J Biol Chem 2005;280:5892–901
  • Huang W, Lv D, Yu H, et al. Dual-target-directed 1,3-diphenylurea derivatives: BACE 1 inhibitor and metal chelator against Alzheimer's disease. Bioorg Med Chem 2010;18:5610–15
  • Joseph R, Ramanujam B, Acharya A, et al. Experimental and computational studies of selective recognition of Hg2+ by amide linked lower rim 1,3-dibenzimidazole derivative of calix[4]arene: species characterization in solution and that in the isolated complex, including the delineation of the nanostructures. J Org Chem 2008;73:5745–58
  • Endo H, Nikaido Y, Nakadate M, et al. Structure activity relationship study of curcumin analogues toward the amyloid-beta aggregation inhibitor. Bioorg Med Chem Lett 2014;24:5621–6
  • Prinz M, Parlar S, Bayraktar G, et al. 1,4-Substituted 4-(1H)-pyridylene-hydrazone-type inhibitors of AChE, BuChE, and amyloid-β aggregation crossing the blood-brain barrier. Eur J Pharm Sci 2013;49:603–13

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.