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Volumn 78, Issue , 2014, Pages 43-53

Synthesis, cytotoxicity and molecular modelling studies of new phenylcinnamide derivatives as potent inhibitors of cholinesterases

Author keywords

Alzheimer's disease; Cholinesterases inhibitors; Cytotoxicity; Molecular docking; Phenylcinnamide derivatives

Indexed keywords

(3 NITROPHENYL) N (3,4,5 TRIMETHOXYPHENYL)ACRYLAMIDE; 2 METHOXY 4 [3 OXO 3 (3,4,5 TRIMETHOXYPHENYLAMINO)PROP 1 ENYL]PHENYL ACETATE; 3 (2 CHLORO 6 NITROPHENYL) N (3,4,5 TRIMETHOXYPHENYL)ACRYLAMIDE; 3 (2 HYDROXY 3 METHOXYPHENYL) N (3,4,5 TRIMETHOXYPHENYL)ACRYLAMIDE; 3 (2 HYDROXY 6 NITROPHENYL) N (3,4,5 TRIMETHOXYPHENYL)ACRYLAMIDE; 3 (2,3 DIHYDROXYPHENYL) N (3,4,5 TRIMETHOXYPHENYL)ACRYLAMIDE; 3 (2,4 DIHYDROXYPHENYL) N (3,4,5 TRIMETHOXYPHENYL)ACRYLAMIDE; 3 (2,6 DIHYDROXYPHENYL) N (3,4,5 TRIMETHOXYPHENYL)ACRYLAMIDE; 3 (3 HYDROXY 4 METHOXYPHENYL) N (3,4,5 TRIMETHOXYPHENYL)ACRYLAMIDE; 3 (4 CHLOROPHENYL) N (3,4,5 TRIMETHOXYPHENYL)ACRYLAMIDE; 3 (4 METHOXYPHENYL) N (3,4,5 TRIMETHOXYPHENYL)ACRYLAMIDE; 3 [2 (ALLYLOXY) PHENYL] N (3,4,5 TRIMETHOXYPHENYL)ACRYLAMIDE; 3 [2 (BENZYLOXY) PHENYL] N (3,4,5 TRIMETHOXYPHENYL)ACRYLAMIDE; 3 [2 (BENZYLOXY)PHENYL] N (3,4,5 TRIMETHOXYPHENYL)ACRYLAMIDE; 3 [3 (BENZYLOXY) 4 METHOXYPHENYL] N (3,4,5 TRIMETHOXYPHENYL)ACRYLAMIDE; 3 [3 (BENZYLOXY)PHENYL] N (3,4,5 TRIMETHOXYPHENYL) ACRYLAMIDE; 3 [3 OXO 3 (3,4,5 TRIMETHOXYPHENYLAMINO)PROP 1 ENYL]PHENYL ACETATE; 3 [4 (ACETOXYAMINO)PHENYL] N (3,4,5 TRIMETHOXYPHENYL) ACRYLAMIDE; 3 [4 (ALLYLOXY)PHENYL] N (3,4,5 TRIMETHOXYPHENYL)ACRYLAMIDE; 3 [4 (BENZYLOXY) 2 HYDROXYPHENYL] N (3,4,5 TRIMETHOXYPHENYL)ACRYLAMIDE; 3 [4 (BENZYLOXY) 3 METHOXYPHENYL] N (3,4,5 TRIMETHOXYPHENYL)ACRYLAMIDE; 4 [3 OXO 3 (3,4,5 TRIMETHOXYPHENYLAMINO)PROP 1 ENYL]PHENYL ACETATE; ACETYLCHOLINESTERASE; ANTINEOPLASTIC AGENT; BENZENE DERIVATIVE; CHOLINESTERASE; CHOLINESTERASE INHIBITOR; PHENYLCINNAMIDE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VINCRISTINE; AMIDE;

EID: 84897073384     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.03.015     Document Type: Article
Times cited : (48)

References (41)
  • 3
    • 0035433962 scopus 로고    scopus 로고
    • Alzheimer's disease and Aβ toxicity: From top to bottom
    • DOI 10.1038/35086072
    • D.H. Small, S. Mok, and J.C. Bornstein Alzheimer's disease and Abeta toxicity: from top to bottom Nature Reviews Neuroscience 2 2001 595 598 (Pubitemid 33679833)
    • (2001) Nature Reviews Neuroscience , vol.2 , Issue.8 , pp. 595-598
    • Small, D.H.1    Mok, S.S.2    Bornstein, J.C.3
  • 6
    • 0042433479 scopus 로고    scopus 로고
    • The cholinergic hypothesis of age and Alzheimer's disease-related cognitive deficits: Recent challenges and their implications for novel drug development
    • DOI 10.1124/jpet.102.041616
    • A.V. Terry, and J.J. Buccafusco The cholinergic hypothesis of age and Alzheimer's disease-related cognitive deficits: recent challenges and their implications for novel drug development Journal of Pharmacology and Experimental Therapeutics 306 2003 821 827 (Pubitemid 37025286)
    • (2003) Journal of Pharmacology and Experimental Therapeutics , vol.306 , Issue.3 , pp. 821-827
    • Terry Jr., A.V.1    Buccafusco, J.J.2
  • 9
    • 80054096801 scopus 로고    scopus 로고
    • Cholinesterases, a target of pharmacology and toxicology
    • M. Pohanka Cholinesterases, a target of pharmacology and toxicology Biomedical Papers 155 2011 219 229
    • (2011) Biomedical Papers , vol.155 , pp. 219-229
    • Pohanka, M.1
  • 13
    • 0027459560 scopus 로고
    • Amino acid residues controlling acetylcholinesterase and butyrylcholinesterase specificity
    • DOI 10.1021/bi00052a003
    • D.C. Vellom, Z. Radic, Y. Li, N.A. Pickering, S. Camp, and P. Taylor Amino acid residues controlling acetylcholinesterase and butyrylcholinesterase specificity Biochemistry 32 1993 12 17 (Pubitemid 23033314)
    • (1993) Biochemistry , vol.32 , Issue.1 , pp. 12-17
    • Vellom, D.C.1    Radic, Z.2    Li, Y.3    Pickering, N.A.4    Camp, S.5    Taylor, P.6
  • 14
    • 0016823110 scopus 로고
    • Interaction of fluorescence probes with acetylcholinesterase. Site and specificity of propidium binding
    • P. Taylor, and S. Lappi Interaction of fluorescence probes with acetylcholinesterase. Site and specificity of propidium binding Biochemistry 14 1975 1989 1997
    • (1975) Biochemistry , vol.14 , pp. 1989-1997
    • Taylor, P.1    Lappi, S.2
  • 16
    • 0037298750 scopus 로고    scopus 로고
    • β-Amyloid aggregation induced by human acetylcholinesterase: Inhibition studies
    • DOI 10.1016/S0006-2952(02)01514-9, PII S0006295202015149
    • M. Bartolini, C. Bertucci, V. Cavrini, and V. Andrisano β-Amyloid aggregation induced by human acetylcholinesterase: inhibition studies Biochemical Pharmacology 65 2003 407 416 (Pubitemid 36084557)
    • (2003) Biochemical Pharmacology , vol.65 , Issue.3 , pp. 407-416
    • Bartolini, M.1    Bertucci, C.2    Cavrini, V.3    Andrisano, V.4
  • 17
    • 0029863697 scopus 로고    scopus 로고
    • Acetylcholinesterase accelerates assembly of amyloid-β-peptides into Alzheimer's fibrils: Possible role of the peripheral site of the enzyme
    • DOI 10.1016/S0896-6273(00)80108-7
    • N.C. Inestrosa, A. Alvarez, C.A. Perez, R.D. Moreno, M. Vicente, C. Linker, O.I. Casanueva, C. Soto, and J. Garrido Acetylcholinesterase accelerates assembly of amyloid-β-peptides into Alzheimer's fibrils: possible role of the peripheral site of the enzyme Neuron 16 1996 881 891 (Pubitemid 26124065)
    • (1996) Neuron , vol.16 , Issue.4 , pp. 881-891
    • Inestrosa, N.C.1    Alvarez, A.2    Perez, C.A.3    Moreno, R.D.4    Vicente, M.5    Linker, C.6    Casanueva, O.I.7    Soto, C.8    Garrido, J.9
  • 18
    • 84866597643 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of 3-thiazolocoumarinyl Schiff-base derivatives as cholinesterase inhibitors
    • R. Raza, A. Saeed, M. Arif, S. Mahmood, M. Muddassar, A. Raza, and J. Iqbal Synthesis and biological evaluation of 3-thiazolocoumarinyl Schiff-base derivatives as cholinesterase inhibitors Chemical Biology & Drug Design 80 2012 605 615
    • (2012) Chemical Biology & Drug Design , vol.80 , pp. 605-615
    • Raza, R.1    Saeed, A.2    Arif, M.3    Mahmood, S.4    Muddassar, M.5    Raza, A.6    Iqbal, J.7
  • 19
    • 4043074138 scopus 로고    scopus 로고
    • Cholinesterase inhibitors: New roles and therapeutic alternatives
    • DOI 10.1016/j.phrs.2003.11.017, PII S1043661804000854
    • E. Giacobini Cholinesterase inhibitors: new roles and therapeutic alternatives Pharmacological Research 50 2004 433 440 (Pubitemid 39078534)
    • (2004) Pharmacological Research , vol.50 , Issue.4 , pp. 433-440
    • Giacobini, E.1
  • 20
    • 0032741056 scopus 로고    scopus 로고
    • Selectivity of cholinesterase inhibition: Clinical implications for the treatment of Alzheimer's disease
    • DOI 10.2165/00023210-199912040-00005
    • M. Weinstock Selectivity of cholinesterase inhibition: clinical implications for the treatment of Alzheimer's disease CNS drugs 12 1999 307 323 (Pubitemid 29503416)
    • (1999) CNS Drugs , vol.12 , Issue.4 , pp. 307-323
    • Weinstock, M.1
  • 22
    • 50249237889 scopus 로고    scopus 로고
    • Design, synthesis, and acetylcholinesterase inhibitory activity of novel coumarin analogues
    • X. Zhou, X.-B. Wang, T. Wang, and L.-Y. Kong Design, synthesis, and acetylcholinesterase inhibitory activity of novel coumarin analogues Bioorganic & Medicinal Chemistry 16 2008 8011 8021
    • (2008) Bioorganic & Medicinal Chemistry , vol.16 , pp. 8011-8021
    • Zhou, X.1    Wang, X.-B.2    Wang, T.3    Kong, L.-Y.4
  • 25
    • 0021268034 scopus 로고
    • Identification of chemotactic lipoxygenase products of arachidonate metabolism in psoriatic skin
    • J. Grabbe, B.M. Czarnetzki, T. Rosenbach, and M. Mardin Identification of chemotactic lipoxygenase products of arachidonate metabolism in psoriatic skin Journal of Investigative Dermatology 82 1984 477 479 (Pubitemid 14101281)
    • (1984) Journal of Investigative Dermatology , vol.82 , Issue.5 , pp. 477-479
    • Grabbe, J.1    Czarnetzki, B.M.2    Rosenbach, T.3    Mardin, M.4
  • 26
    • 0027336017 scopus 로고
    • 4 induces lung injury in the rabbit: Role of neutrophils and effect of indomethacin
    • K. Yoshimura, S. Nakagawa, S. Koyama, T. Kobayashi, and T. Homma Leukotriene B4 induces lung injury in the rabbit: role of neutrophils and effect of indomethacin Journal of Applied Physiology 74 1993 2174 2179 (Pubitemid 23157036)
    • (1993) Journal of Applied Physiology , vol.74 , Issue.5 , pp. 2174-2179
    • Yoshimura, K.1    Nakagawa, S.2    Koyama, S.3    Kobayashi, T.4    Homma, T.5
  • 28
    • 0025917868 scopus 로고
    • Relationship between leukotriene B4 and immunological parameters in rheumatoid synovial fluids
    • N. Ahmadzadeh, M. Shingu, M. Nobunaga, and T. Tawara Relationship between leukotriene B4 and immunological parameters in rheumatoid synovial fluids Inflammation 15 1991 497 503
    • (1991) Inflammation , vol.15 , pp. 497-503
    • Ahmadzadeh, N.1    Shingu, M.2    Nobunaga, M.3    Tawara, T.4
  • 30
    • 79960281863 scopus 로고    scopus 로고
    • Organocatalytic decarboxylative Doebner-Knoevenagel reactions between arylaldehydes and monoethyl malonate mediated by a bifunctional polymeric catalyst
    • J. Lu, and P.H. Toy Organocatalytic decarboxylative Doebner-Knoevenagel reactions between arylaldehydes and monoethyl malonate mediated by a bifunctional polymeric catalyst Synlett 2011 1723 1726
    • (2011) Synlett , pp. 1723-1726
    • Lu, J.1    Toy, P.H.2
  • 31
    • 0021079957 scopus 로고
    • Syntheses and anti-inflammatory and analgesic activities of hydroxamic acids and acid hydrazides
    • K. Tanaka, K. Matsuo, A. Nakanishi, T. Hatano, H. Izeki, Y. Ishida, and W. Mori Syntheses and anti-inflammatory and analgesic activities of hydroxamic acids and acid hydrazides Chemical & Pharmaceutical Bulletin (Tokyo) 31 1983 2810 2819 (Pubitemid 14233246)
    • (1983) Chemical and Pharmaceutical Bulletin , vol.31 , Issue.8 , pp. 2810-2819
    • Tanaka, K.1    Matsuo, K.2    Nakanishi, A.3
  • 32
    • 0033465958 scopus 로고    scopus 로고
    • Development of a process for triazine-promoted amidation of carboxylic acids
    • H.L. Rayle, and L. Fellmeth Development of a process for triazine-promoted amidation of carboxylic acids Organic Process Research & Development 3 1999 172 176
    • (1999) Organic Process Research & Development , vol.3 , pp. 172-176
    • Rayle, H.L.1    Fellmeth, L.2
  • 33
    • 20944433279 scopus 로고    scopus 로고
    • Synthesis and identification of small molecules that potently induce apoptosis in melanoma cells through G1 cell cycle arrest
    • DOI 10.1021/ja042913p
    • R.S. Dothager, K.S. Putt, B.J. Allen, B.J. Leslie, V. Nesterenko, and P.J. Hergenrother Synthesis and identification of small molecules that potently induce apoptosis in melanoma cells through G1 cell cycle arrest Journal of the American Chemical Society 127 2005 8686 8696 (Pubitemid 40868251)
    • (2005) Journal of the American Chemical Society , vol.127 , Issue.24 , pp. 8686-8696
    • Dothager, R.S.1    Putt, K.S.2    Allen, B.J.3    Leslie, B.J.4    Nesterenko, V.5    Hergenrother, P.J.6
  • 35
    • 18344404686 scopus 로고    scopus 로고
    • Substance P-induced cadherin expression and its signal transduction in a cloned human corneal epithelial cell line
    • DOI 10.1002/(SICI)1097-4652(200002) 182:2<189::AID-JCP7>3.0.CO;2-9
    • K. Araki-Sasaki, S. Aizawa, M. Hiramoto, M. Nakamura, O. Iwase, K. Nakata, Y. Sasaki, T. Mano, H. Handa, and Y. Tano Substance P-induced cadherin expression and its signal transduction in a cloned human corneal epithelial cell line Journal of Cellular Physiology 182 2000 189 195 (Pubitemid 30022671)
    • (2000) Journal of Cellular Physiology , vol.182 , Issue.2 , pp. 189-195
    • Araki-Sasaki, K.1    Aizawa, S.2    Hiramoto, M.3    Nakamura, M.4    Iwase, O.5    Nakata, K.6    Sasaki, Y.7    Mano, T.8    Handa, H.9    Tano, Y.10
  • 38
    • 68349117038 scopus 로고    scopus 로고
    • Computational docking of biomolecular complexes with AutoDock
    • pdb prot5200
    • D.S. Goodsell Computational docking of biomolecular complexes with AutoDock Cold Spring Harbor Protocols 2009 2009 pdb prot5200
    • (2009) Cold Spring Harbor Protocols , vol.2009
    • Goodsell, D.S.1
  • 39


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