메뉴 건너뛰기




Volumn 21, Issue 4, 2016, Pages

Imidazopyranotacrines as Non-Hepatotoxic, Selective Acetylcholinesterase Inhibitors, and Antioxidant Agents for Alzheimer's Disease Therapy

Author keywords

Alzheimer's disease; Antioxidant activity; Cholinesterase inhibitors; Hepatotoxicity; ORAC; Tacrine analogues

Indexed keywords

ANTIOXIDANT; CHOLINESTERASE INHIBITOR; IMIDAZOLE DERIVATIVE; TACRINE;

EID: 84967180403     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules21040400     Document Type: Article
Times cited : (23)

References (43)
  • 1
    • 84862323532 scopus 로고    scopus 로고
    • Towards Alzheimer's root cause: ECSIT as an integrating hub between oxidative stress, inflammation and mitochondrial dysfunction. Hypothetical role of the adapter protein ECSIT in familial and sporadic Alzheimer's disease pathogenesis
    • [CrossRef] [PubMed]
    • Soler-López, M.; Badiola, N.; Zanzoni, A.; Aloy, P. Towards Alzheimer's root cause: ECSIT as an integrating hub between oxidative stress, inflammation and mitochondrial dysfunction. Hypothetical role of the adapter protein ECSIT in familial and sporadic Alzheimer's disease pathogenesis. Bioessays 2012, 34, 532-541. [CrossRef] [PubMed]
    • (2012) Bioessays , vol.34 , pp. 532-541
    • Soler-López, M.1    Badiola, N.2    Zanzoni, A.3    Aloy, P.4
  • 2
    • 79952574501 scopus 로고    scopus 로고
    • Epidemiology of Alzheimer disease
    • [CrossRef] [PubMed]
    • Reitz, C.; Brayne, C.; Mayeux, R. Epidemiology of Alzheimer disease. Nat. Rev. Neurol. 2011, 7, 137-152. [CrossRef] [PubMed]
    • (2011) Nat. Rev. Neurol. , vol.7 , pp. 137-152
    • Reitz, C.1    Brayne, C.2    Mayeux, R.3
  • 4
    • 78751644048 scopus 로고    scopus 로고
    • Amyloid-β tau - A toxic pas de deux in Alzheimer's disease
    • [CrossRef] [PubMed]
    • Ittner, L.M.; Götz, J. Amyloid-β and tau-a toxic pas de deux in Alzheimer's disease. Nat. Rev. Neurosci. 2011, 12, 65-72. [CrossRef] [PubMed]
    • (2011) Nat. Rev. Neurosci. , vol.12 , pp. 65-72
    • Ittner, L.M.1    Götz, J.2
  • 5
    • 33745140951 scopus 로고    scopus 로고
    • Tau phosphorylation and aggregation in Alzheimer's disease pathology
    • [CrossRef] [PubMed]
    • Ávila, J. Tau phosphorylation and aggregation in Alzheimer's disease pathology. FEBS Lett. 2006, 580, 2922-2927. [CrossRef] [PubMed]
    • (2006) FEBS Lett. , vol.580 , pp. 2922-2927
    • Ávila, J.1
  • 6
    • 84898425209 scopus 로고    scopus 로고
    • Oxidative stress in Alzheimer's disease: Are we connecting the dots?
    • [CrossRef] [PubMed]
    • Rosini, M.; Simoni, E.; Milelli, A.; Minarini, A.; Melchiorre, C. Oxidative stress in Alzheimer's disease: Are we connecting the dots? J. Med. Chem. 2014, 57, 2821-2831. [CrossRef] [PubMed]
    • (2014) J. Med. Chem. , vol.57 , pp. 2821-2831
    • Rosini, M.1    Simoni, E.2    Milelli, A.3    Minarini, A.4    Melchiorre, C.5
  • 8
    • 0141642240 scopus 로고    scopus 로고
    • Acetylcholinesterase induces neuronal cell loss, astrocyte hypertrophy and behavioral deficits in mammalian hippocampus
    • [CrossRef] [PubMed]
    • Chacón, M.A.; Reyes, A.E.; Inestrosa, N.C. Acetylcholinesterase induces neuronal cell loss, astrocyte hypertrophy and behavioral deficits in mammalian hippocampus. J. Neurochem. 2003, 87, 195-204. [CrossRef] [PubMed]
    • (2003) J. Neurochem , vol.87 , pp. 195-204
    • Chacón, M.A.1    Reyes, A.E.2    Inestrosa, N.C.3
  • 9
    • 53149107135 scopus 로고    scopus 로고
    • Cognitive dysfunction in neuropsychiatric disorders: Selected serotonin receptor subtypes as therapeutic targets
    • [CrossRef] [PubMed]
    • Terry, A.V.; Buccafusco, J.J.; Wilson, C. Cognitive dysfunction in neuropsychiatric disorders: Selected serotonin receptor subtypes as therapeutic targets. Behav. Brain Res. 2008, 195, 30-38. [CrossRef] [PubMed]
    • (2008) Behav. Brain Res. , vol.195 , pp. 30-38
    • Terry, A.V.1    Buccafusco, J.J.2    Wilson, C.3
  • 10
    • 51349134160 scopus 로고    scopus 로고
    • Hope in Alzheimer's fight emerges from unexpected places
    • [CrossRef] [PubMed]
    • Gura, T. Hope in Alzheimer's fight emerges from unexpected places. Nat. Med. 2008, 14, 894. [CrossRef] [PubMed]
    • (2008) Nat. Med. , vol.14 , pp. 894
    • Gura, T.1
  • 12
    • 33750883640 scopus 로고    scopus 로고
    • Targeting beta-amyloid pathogenesis through acetylcholinesterase inhibitors
    • [CrossRef] [PubMed]
    • Castro, A.; Martínez, A. Targeting Beta-Amyloid Pathogenesis Through Acetylcholinesterase Inhibitors. Curr. Pharm. Des. 2006, 12, 4377-4387. [CrossRef] [PubMed]
    • (2006) Curr. Pharm. Des. , vol.12 , pp. 4377-4387
    • Castro, A.1    Martínez, A.2
  • 13
    • 84896927108 scopus 로고    scopus 로고
    • Polypharmacology: The rise of multitarget drugs over combination therapies
    • [CrossRef] [PubMed]
    • Rosini, M. Polypharmacology: The rise of multitarget drugs over combination therapies. Future Med. Chem. 2014, 6, 485-487. [CrossRef] [PubMed]
    • (2014) Future Med. Chem. , vol.6 , pp. 485-487
    • Rosini, M.1
  • 14
    • 84871094408 scopus 로고    scopus 로고
    • Recent advances in the multitarget-directed ligands approach for the treatment of Alzheimer's disease
    • [CrossRef] [PubMed]
    • León, R.; García, A.G.; Marco-Contelles, J. Recent advances in the multitarget-directed ligands approach for the treatment of Alzheimer's disease. Med. Res. Rev. 2013, 33, 139-189. [CrossRef] [PubMed]
    • (2013) Med. Res. Rev. , vol.33 , pp. 139-189
    • León, R.1    García, A.G.2    Marco-Contelles, J.3
  • 15
    • 84875209476 scopus 로고    scopus 로고
    • Novel tacrine-related drugs as potential candidates for the treatment of Alzheimer's disease
    • [CrossRef] [PubMed]
    • Romero, A.; Cacabelos, R.; Oset-Gasque, M.J.; Samadi, A.; Marco-Contelles, J. Novel tacrine-related drugs as potential candidates for the treatment of Alzheimer's disease. Bioorg. Med. Chem. Lett. 2013, 23, 1916-1922. [CrossRef] [PubMed]
    • (2013) Bioorg. Med. Chem. Lett. , vol.23 , pp. 1916-1922
    • Romero, A.1    Cacabelos, R.2    Oset-Gasque, M.J.3    Samadi, A.4    Marco-Contelles, J.5
  • 16
    • 84904754895 scopus 로고    scopus 로고
    • Selective acetyl and butyrylcholinesterase inhibitors reduce amyloid-beta ex vivo activation of peripheral chemo-cytokines from Alzheimer's disease subjects: Exploring the cholinergic anti-inflammatory pathway
    • [CrossRef] [PubMed]
    • Reale, M.; Di Nicola, M.; Velluto, L.; D'Angelo, C.; Costantini, E.; Lahiri, D.K.; Kamal, M.A.; Yu, Q.S.; Greig, N.H. Selective acetyl and butyrylcholinesterase inhibitors reduce amyloid-beta ex vivo activation of peripheral chemo-cytokines from Alzheimer's disease subjects: Exploring the cholinergic anti-inflammatory pathway. Curr. Alzheimer Res. 2014, 11, 608-622. [CrossRef] [PubMed]
    • (2014) Curr. Alzheimer Res. , vol.11 , pp. 608-622
    • Reale, M.1    Di Nicola, M.2    Velluto, L.3    D'Angelo, C.4    Costantini, E.5    Lahiri, D.K.6    Kamal, M.A.7    Yu, Q.S.8    Greig, N.H.9
  • 17
    • 0028316959 scopus 로고
    • Hepatotoxic effects of tacrine administration in patients with Alzheimer's disease
    • [CrossRef] [PubMed]
    • Watkins, P.B.; Zimmerman, H.J.; Knapp, M.J.; Gracon, S.I.; Lewis, K.W. Hepatotoxic effects of tacrine administration in patients with Alzheimer's disease. JAMA 1994, 271, 992-998. [CrossRef] [PubMed]
    • (1994) JAMA , vol.271 , pp. 992-998
    • Watkins, P.B.1    Zimmerman, H.J.2    Knapp, M.J.3    Gracon, S.I.4    Lewis, K.W.5
  • 19
    • 84955134350 scopus 로고    scopus 로고
    • Novel tacrine-benzofuran hybrids as potent multitarget-directed ligands for the treatment of Alzheimer's disease: Design, synthesis, biological evaluation, and X-ray crystallography
    • [CrossRef] [PubMed]
    • Zha, X.; Lamba, D.; Zhang, L.; Lou, Y.; Xu, C.; Kang, D.; Chen, L.; Xu, Y.; Zhang, L.; De Simone, A.; et al. Novel tacrine-benzofuran hybrids as potent multitarget-directed ligands for the treatment of Alzheimer's disease: Design, synthesis, biological evaluation, and X-ray crystallography. J. Med. Chem. 2016, 59, 114-131. [CrossRef] [PubMed]
    • (2016) J. Med. Chem. , vol.59 , pp. 114-131
    • Zha, X.1    Lamba, D.2    Zhang, L.3    Lou, Y.4    Xu, C.5    Kang, D.6    Chen, L.7    Xu, Y.8    Zhang, L.9    De Simone, A.10
  • 20
    • 0344074660 scopus 로고    scopus 로고
    • Friedländer reaction on 2-amino-3-cyano-4H-pyrans: Synthesis of derivatives of 4H-pyran[2,3-b]quinoline, new tacrine analogues
    • [CrossRef]
    • Martínez-Grau, A.; Marco, J.L. Friedländer reaction on 2-amino-3-cyano-4H-pyrans: Synthesis of derivatives of 4H-pyran[2,3-b]quinoline, new tacrine analogues. Bioorg. Med. Chem. Lett. 1997, 7, 3165-3170. [CrossRef]
    • (1997) Bioorg. Med. Chem. Lett. , vol.7 , pp. 3165-3170
    • Martínez-Grau, A.1    Marco, J.L.2
  • 21
    • 0035105750 scopus 로고    scopus 로고
    • Synthesis and acetylcholinesterase/butyrylcholinesterase inhibition activity of new tacrine-like analogues
    • [CrossRef]
    • Marco, J.L.; de los Ríos, C.; Carreiras, M.C.; Baños, J.E.; Badía, A.; Vivas, N.M. Synthesis and acetylcholinesterase/ butyrylcholinesterase inhibition activity of new tacrine-like analogues. Bioorg. Med. Chem. 2001, 9, 727-732. [CrossRef]
    • (2001) Bioorg. Med. Chem. , vol.9 , pp. 727-732
    • Marco, J.L.1    De Los Ríos, C.2    Carreiras, M.C.3    Baños, J.E.4    Badía, A.5    Vivas, N.M.6
  • 22
    • 12944262130 scopus 로고    scopus 로고
    • Synthesis, acetylcholinesterase inhibition and neuroprotective activity of new tacrine analogues
    • [CrossRef] [PubMed]
    • León, R.; Marco-Contelles, J.; García, A.G.; Villarroya, M. Synthesis, acetylcholinesterase inhibition and neuroprotective activity of new tacrine analogues. Bioorg. Med. Chem. 2005, 13, 1167-1175. [CrossRef] [PubMed]
    • (2005) Bioorg. Med. Chem. , vol.13 , pp. 1167-1175
    • León, R.1    Marco-Contelles, J.2    García, A.G.3    Villarroya, M.4
  • 23
    • 33845327840 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of new 4H-pyrano
    • [CrossRef] [PubMed]
    • Marco-Contelles, J.; León, R.; López, M.G.; García, A.G.; Villarroya, M. Synthesis and biological evaluation of new 4H-pyrano[2,3-b]quinoline derivatives that block acetylcholinesterase and cell calcium signals, and cause neuroprotection against calcium overload and free radicals. Eur. J. Med. Chem. 2006, 41, 1464-1469. [CrossRef] [PubMed]
    • (2006) Eur. J. Med. Chem. , Issue.2-3 , pp. 1464-1469
    • Marco-Contelles, J.1    León, R.2    López, M.G.3    García, A.G.4    Villarroya, M.5
  • 24
    • 84987159689 scopus 로고
    • Synthesis, molecular structure, and complexation of 1,4-dihydropyridines containing ligands for intramolecular complexation of metal electrophiles
    • [CrossRef]
    • Kaptein, B.; Kellogg, R.M.; van Bolhuis, F. Synthesis, molecular structure, and complexation of 1,4-dihydropyridines containing ligands for intramolecular complexation of metal electrophiles. Recl. Trav. Chim. Pays-Bas 1990, 109, 388-395. [CrossRef]
    • (1990) Recl. Trav. Chim. Pays-Bas , vol.109 , pp. 388-395
    • Kaptein, B.1    Kellogg, R.M.2    Van Bolhuis, F.3
  • 25
    • 0346690184 scopus 로고    scopus 로고
    • Design, synthesis and structure-affinity relationships of aryloxyanilide derivatives as novel peripheral benzodiazepine receptor ligands
    • [CrossRef] [PubMed]
    • Okubo, T.; Yoshikawa, R.; Chaki, S.; Okuyama, S.; Nakazato, A. Design, synthesis and structure-affinity relationships of aryloxyanilide derivatives as novel peripheral benzodiazepine receptor ligands. Bioorg. Med. Chem. 2004, 12, 423-438. [CrossRef] [PubMed]
    • (2004) Bioorg. Med. Chem. , vol.12 , pp. 423-438
    • Okubo, T.1    Yoshikawa, R.2    Chaki, S.3    Okuyama, S.4    Nakazato, A.5
  • 27
    • 33644811612 scopus 로고
    • A new and rapid colorimetric determination of acetylcholinesterase activity
    • [CrossRef]
    • Ellman, G.L.; Courtney, K.D.; Andres, V., Jr.; Featherstone, R.M. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem. Pharmacol. 1961, 7, 88-95. [CrossRef]
    • (1961) Biochem. Pharmacol. , Issue.7 , pp. 88-95
    • Ellman, G.L.1    Courtney, K.D.2    Andres, V.3    Featherstone, R.M.4
  • 28
    • 42949132291 scopus 로고    scopus 로고
    • Design and synthesis of tacrine-ferulic acid hybrids as multi-potent anti-Alzheimer drug candidates
    • [CrossRef] [PubMed]
    • Fang, L.; Kraus, B.; Lehmann, J.; Heilmann, J.; Zhang, Y.; Decker, M. Design and synthesis of tacrine-ferulic acid hybrids as multi-potent anti-Alzheimer drug candidates. Bioorg. Med. Chem. Lett. 2008, 18, 2905-2909. [CrossRef] [PubMed]
    • (2008) Bioorg. Med. Chem. Lett. , Issue.18 , pp. 2905-2909
    • Fang, L.1    Kraus, B.2    Lehmann, J.3    Heilmann, J.4    Zhang, Y.5    Decker, M.6
  • 29
    • 0015972948 scopus 로고
    • A simple graphical method for determining the inhibition constants of mixed, uncompetitive and non-competitive inhibitors (Short Communication)
    • [CrossRef] [PubMed]
    • Cornish-Bowden, A. A simple graphical method for determining the inhibition constants of mixed, uncompetitive and non-competitive inhibitors (Short Communication). Biochem. J. 1974, 137, 143-144. [CrossRef] [PubMed]
    • (1974) Biochem , vol.137 , pp. 143-144
    • Cornish-Bowden, A.1
  • 30
    • 17344380047 scopus 로고    scopus 로고
    • Extending applicability of the oxygen radical absorbance capacity (ORAC-fluorescein) assay
    • [CrossRef] [PubMed]
    • 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. [CrossRef] [PubMed]
    • (2004) J. Agric. Food Chem. , vol.52 , pp. 4854
    • Dávalos, A.1    Gómez-Cordovés, C.2    Bartolomé, B.3
  • 31
    • 33747084103 scopus 로고    scopus 로고
    • High concordance of drug-induced human hepatotoxicity with in vitro cytotoxicity measured in a novel cell-based model using high content screening
    • [CrossRef] [PubMed]
    • O'Brien, P.J.; Irwin, W.; Diaz, D.; Howard-Cofield, E.; Krejsa, C.M.; Slaughter, M.R.; Gao, B.; Kaludercic, N.; Angeline, A.; Bernardi, P.; et al. High concordance of drug-induced human hepatotoxicity with in vitro cytotoxicity measured in a novel cell-based model using high content screening. Arch. Toxicol. 2006, 80, 580-604 [CrossRef] [PubMed]
    • (2006) Arch. Toxicol. , vol.80 , pp. 580-604
    • O'Brien, P.J.1    Irwin, W.2    Diaz, D.3    Howard-Cofield, E.4    Krejsa, C.M.5    Slaughter, M.R.6    Gao, B.7    Kaludercic, N.8    Angeline, A.9    Bernardi, P.10
  • 32
    • 17044433346 scopus 로고    scopus 로고
    • Cytotoxic effects of 100 reference compounds on Hep G2 and HeLa cells and of 60 compounds on ECC-1 and CHO cells. I mechanistic assays on ROS, glutathione depletion and calcein uptake
    • [CrossRef] [PubMed]
    • Schoonen, W.G.E.J.; Westerink, W.M.A.; de Roos, J.A.D.M.; Débiton, E. Cytotoxic effects of 100 reference compounds on Hep G2 and HeLa cells and of 60 compounds on ECC-1 and CHO cells. I mechanistic assays on ROS, glutathione depletion and calcein uptake. Toxicol. In Vitro 2005, 19, 505-516. [CrossRef] [PubMed]
    • (2005) Toxicol. Vitro , vol.19 , pp. 505-516
    • Schoonen, W.G.E.J.1    Westerink, W.M.A.2    De Roos, J.A.D.M.3    Débiton, E.4
  • 33
    • 0022445670 scopus 로고
    • Rapid colorimetric assay for cell growth and survival. Modifications to the tetrazolium dye procedure giving improved sensitivity and reliability
    • [CrossRef]
    • 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, 271-277. [CrossRef]
    • (1986) J. Immunol. Methods , vol.89 , pp. 271-277
    • Denizot, F.1    Lang, R.2
  • 34
    • 84965135749 scopus 로고
    • 2nd ed.;Longmans, Green and Co. :London, UK
    • Dixon, M.; Webb, E.C. Enzymes, 2nd ed.; Longmans, Green and Co.: London, UK, 1964; pp. 54-166.
    • (1964) Enzymes , pp. 54-166
    • Dixon, M.1    Webb, E.C.2
  • 36
    • 77951782384 scopus 로고    scopus 로고
    • Current therapeutic targets for the treatment of Alzheimer's disease
    • [CrossRef] [PubMed]
    • Grill, J.D.; Cummings, J.L. Current therapeutic targets for the treatment of Alzheimer's disease. Expert Rev. Neurother. 2010, 10, 711-728. [CrossRef] [PubMed]
    • (2010) Expert Rev. Neurother. , vol.10 , pp. 711-728
    • Grill, J.D.1    Cummings, J.L.2
  • 37
    • 84893778864 scopus 로고    scopus 로고
    • Semagacestat's fall: Where next for AD therapies? Nat
    • Haass, C. Semagacestat's fall: Where next for AD therapies? Nat. Med. 2013, 19, 1214-1215.
    • (2013) Med , vol.19 , pp. 1214-1215
    • Haass, C.1
  • 39
    • 84923350577 scopus 로고    scopus 로고
    • Novel tacrine-grafted Ugi adducts as multipotent anti-Alzheimer drugs: A synthetic renewal in tacrine-ferulic acid hybrids
    • [CrossRef] [PubMed]
    • Benchekroun, M.; Bartolini, M.; Egea, J.; Romero, A.; Soriano, E.; Pudlo, M.; Luzet, V.; Andrisano, V.; Jimeno, M.L.; López, M.G.; et al. Novel tacrine-grafted Ugi adducts as multipotent anti-Alzheimer drugs: A synthetic renewal in tacrine-ferulic acid hybrids. Chem. Med. Chem. 2015, 10, 523-539. [CrossRef] [PubMed]
    • (2015) Chem. Med. Chem. , vol.10 , pp. 523-539
    • Benchekroun, M.1    Bartolini, M.2    Egea, J.3    Romero, A.4    Soriano, E.5    Pudlo, M.6    Luzet, V.7    Andrisano, V.8    Jimeno, M.L.9    López, M.G.10
  • 40
    • 84908375105 scopus 로고    scopus 로고
    • Multitarget drug design strategy: Quinone-tacrine hybrids designed to block amyloid-beta aggregation and to exert anticholinesterase and antioxidant effects
    • [CrossRef] [PubMed]
    • Nepovimova, E.; Uliassi, E.; Korabecny, J.; Pena-Altamira, L.E.; Samez, S.; Pesaresi, A.; Garcia, G.E.; Bartolini, M.; Andrisano, V.; Bergamini, C.; et al. Multitarget drug design strategy: Quinone-tacrine hybrids designed to block amyloid-beta aggregation and to exert anticholinesterase and antioxidant effects. J. Med. Chem. 2014, 57, 8576-8589. [CrossRef] [PubMed]
    • (2014) J. Med. Chem. , vol.57 , pp. 8576-8589
    • Nepovimova, E.1    Uliassi, E.2    Korabecny, J.3    Pena-Altamira, L.E.4    Samez, S.5    Pesaresi, A.6    Garcia, G.E.7    Bartolini, M.8    Andrisano, V.9    Bergamini, C.10
  • 42
    • 84861048527 scopus 로고    scopus 로고
    • Tacrine-ferulic acid-nitric oxide (NO) donor trihybrids as potent, multifunctional acetyl- and butyrylcholinesterase inhibitors
    • [CrossRef] [PubMed]
    • Chen, Y.; Sun, J.; Fang, L.; Liu, M.; Peng, S.; Liao, H.; Lehmann, J.; Zhang, Y. Tacrine-ferulic acid-nitric oxide (NO) donor trihybrids as potent, multifunctional acetyl- and butyrylcholinesterase inhibitors. J. Med. Chem. 2012, 55, 4309-4321. [CrossRef] [PubMed]
    • (2012) J. Med. Chem. , vol.55 , pp. 4309-4321
    • Chen, Y.1    Sun, J.2    Fang, L.3    Liu, M.4    Peng, S.5    Liao, H.6    Lehmann, J.7    Zhang, Y.8
  • 43
    • 77954331097 scopus 로고    scopus 로고
    • Novel tacrine-8-hydroxyquinoline hybrids as multifunctional agents for the treatment of Alzheimer's disease, with neuroprotective, cholinergic, antioxidant, and copper-complexing properties
    • [CrossRef] [PubMed]
    • Fernández-Bachiller, M.I.; Pérez, C.; González-Muñoz, G.C.; Conde, S.; López, M.G.; Villarroya, M.; García, A.G.; Rodríguez-Franco, M.I. 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, 4927-4937. [CrossRef] [PubMed]
    • (2010) J. Med. Chem. , vol.53 , pp. 4927-4937
    • Fernández-Bachiller, M.I.1    Pérez, C.2    González-Muñoz, G.C.3    Conde, S.4    López, M.G.5    Villarroya, M.6    García, A.G.7    Rodríguez-Franco, M.I.8


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.