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Research Article

Synthesis and biological evaluation of novel N,N′-bis-methylenedioxybenzyl-alkylenediamines as bivalent anti-Alzheimer disease ligands

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Pages 706-711 | Received 14 Aug 2010, Accepted 09 Dec 2010, Published online: 21 Jan 2011

References

  • Fernández-Bachiller MI, Pérez C, Campillo NE, Páez JA, González-Muñoz GC, Usán P et al. Tacrine-melatonin hybrids as multifunctional agents for Alzheimer’s disease, with cholinergic, antioxidant, and neuroprotective properties. Chemmedchem 2009;4:828–841.
  • Rizzo S, Rivière C, Piazzi L, Bisi A, Gobbi S, Bartolini M et al. Benzofuran-based hybrid compounds for the inhibition of cholinesterase activity, beta amyloid aggregation, and abeta neurotoxicity. J Med Chem 2008;51:2883–2886.
  • Tumiatti V, Milelli A, Minarini A, Rosini M, Bolognesi ML, Micco M et al. Structure–activity relationships of acetylcholinesterase noncovalent inhibitors based on a polyamine backbone. 4. Further investigation on the inner spacer. J Med Chem 2008;51:7308–7312.
  • Cavalli A, Bolognesi ML, Minarini A, Rosini M, Tumiatti V, Recanatini M et al. Multi-target-directed ligands to combat neurodegenerative diseases. J Med Chem 2008;51:347–372.
  • Howlett DR, Perry AE, Godfrey F, Swatton JE, Jennings KH, Spitzfaden C et al. Inhibition of fibril formation in beta-amyloid peptide by a novel series of benzofurans. Biochem J 1999;340 (Pt 1):283–289.
  • Thorsett ED, Latimer LH. Therapeutic approaches to Alzheimer’s disease. Curr Opin Chem Biol 2000;4:377–382.
  • Wolfe MS, Citron M, Diehl TS, Xia W, Donkor IO, Selkoe DJ. A substrate-based difluoro ketone selectively inhibits Alzheimer’s gamma-secretase activity. J Med Chem 1998;41:6–9.
  • Yang F, Lim GP, Begum AN, Ubeda OJ, Simmons MR, Ambegaokar SS et al. Curcumin inhibits formation of amyloid beta oligomers and fibrils, binds plaques, and reduces amyloid in vivo. J Biol Chem 2005;280:5892–5901.
  • Lim GP, Chu T, Yang F, Beech W, Frautschy SA, Cole GM. The curry spice curcumin reduces oxidative damage and amyloid pathology in an Alzheimer transgenic mouse. J Neurosci 2001;21:8370–8377.
  • Ono M, Kung MP, Hou C, Kung HF. Benzofuran derivatives as Abeta-aggregate-specific imaging agents for Alzheimer’s disease. Nucl Med Biol 2002;29:633–642.
  • Kuo YH, Wu MD, Hung CC, Huang RL, Yang Kuo LM, Shen YC et al. Syntheses of C(18) dibenzocyclooctadiene lignan derivatives as anti-HBsAg and anti-HBeAg agents. Bioorg Med Chem 2005;13:1555–1561.
  • Hung TM, Na M, Min BS, Ngoc TM, Lee I, Zhang X et al. Acetylcholinesterase inhibitory effect of lignans isolated from Schizandra chinensis. Arch Pharm Res 2007;30:685–690.
  • Liu W, Yu R, Wu JH, Luo HM. [Gamma-Schisandrin inhibits production of amyloid beta-protein 42 in M146L cells]. Yao Xue Xue Bao 2006;41:1136–1140.
  • Tomita M, Aoyagi Y. Cupric oxide as an efficient catalyst for the methylenation of catechols. Chem Pharm Bull 1968;16:523–526.
  • Schneiders GE, Stevenson R. Structure and synthesis of (±)-Wuweizisu C. J Org Chem 1981;46:2969–2971.
  • Mckittrick B. A., Stevenson R. Synthesis of the yeast antioxidant benzofuran and analogues. J Chem Soc Perkin Trans 1984;4:709–712.
  • James EE, Steven RL. A convenient synthesis of 3,4-dimethoxy-5-hydroxy- benzaldehyde. Synth Commun 1998;28:1517–1524.
  • Zhou JJ, Huang H, Xie SQ, Wang YX, Zhao J, Wang CJ. The synthesis and molecular recognization of the polyamine transporter of hydrazine-modified diamine conjugates. Chin Chem Lett 2008;19:99–101.
  • Qiu X, Liu Z, Shao WY, Liu X, Jing DP, Yu YJ et al. Synthesis and evaluation of curcumin analogues as potential thioredoxin reductase inhibitors. Bioorg Med Chem 2008;16:8035–8041.
  • Ellman GL, Courtney KD, Andres V Jr, Feather-Stone RM. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol 1961;7:88–95.
  • Rosini M, Simoni E, Bartolini M, Cavalli A, Ceccarini L, Pascu N 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;51:4381–4384.
  • Elsinghorst PW, Tanarro CM, Gütschow M. Novel heterobivalent tacrine derivatives as cholinesterase inhibitors with notable selectivity toward butyrylcholinesterase. J Med Chem 2006;49:7540–7544.
  • Pan L, Tan JH, Hou JQ, Huang SL, Gu LQ, Huang ZS. Design, synthesis and evaluation of isaindigotone derivatives as acetylcholinesterase and butyrylcholinesterase inhibitors. Bioorg Med Chem Lett 2008;18:3790–3793.

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