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Volumn 40, Issue 22, 1997, Pages 3516-3523

Novel tacrine analogues for potential use against Alzheimer's disease: Potent and selective acetylcholinesterase inhibitors and 5-HT uptake inhibitors

Author keywords

[No Author keywords available]

Indexed keywords

13 AMINO 6,7 DIHYDRO 5H BENZO[3,4]CYCLOHEPTA[1,2 B]QUINOLINE; 6 AMINO 4,5 BENZO 5H CYCLOPENTA[1,2 B]QUINOLINE; ACETYLCHOLINESTERASE; SEROTONIN UPTAKE INHIBITOR; TACRINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0030725741     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm970150t     Document Type: Article
Times cited : (119)

References (50)
  • 1
    • 0021977076 scopus 로고
    • Alzheimer's disease
    • (a) Wurtman, R. J. Alzheimer's disease. Sci. Am. 1985, 252, 48-56.
    • (1985) Sci. Am. , vol.252 , pp. 48-56
    • Wurtman, R.J.1
  • 3
    • 0011162190 scopus 로고
    • Selective loss of cholinergic neurones in Alzheimer's disease
    • (a) Davies, P.; Maloney, A. J. F. Selective loss of cholinergic neurones in Alzheimer's disease. Lancet 1976, No. 2, 1403.
    • (1976) Lancet , Issue.2 , pp. 1403
    • Davies, P.1    Maloney, A.J.F.2
  • 4
    • 0017133142 scopus 로고
    • Neurotransmitter-related enzymes and indices of hypoxia in senile dementia
    • (b) Bowen, D. M.; Smith, C. B.; White, P.; Dawson, A. N. Neurotransmitter-related enzymes and indices of hypoxia in senile dementia. Brain 1976, 99, 459.
    • (1976) Brain , vol.99 , pp. 459
    • Bowen, D.M.1    Smith, C.B.2    White, P.3    Dawson, A.N.4
  • 5
    • 0022643823 scopus 로고
    • Non-cholinergic neurotransmitter abmormalities in Alzheimer's disease
    • Iversen, L. L.; Rossor, M. Non-cholinergic neurotransmitter abmormalities in Alzheimer's disease. Br. Med. Bull. 1986, 42, 70-74.
    • (1986) Br. Med. Bull. , vol.42 , pp. 70-74
    • Iversen, L.L.1    Rossor, M.2
  • 6
    • 0022645755 scopus 로고
    • The cholinergic hypothesis-ten years on
    • Perry, E. K. The cholinergic hypothesis-ten years on. Br. Med. Bull. 1986, 42, 63-69.
    • (1986) Br. Med. Bull. , vol.42 , pp. 63-69
    • Perry, E.K.1
  • 7
    • 0021357235 scopus 로고
    • The effects of 4-aminopyridine in elderly patients with Alzheimer's disease
    • Wesseling, A.; Agoston, S. The effects of 4-aminopyridine in elderly patients with Alzheimer's disease. N. Engl. J. Med. 1988, 310, 988.
    • (1988) N. Engl. J. Med. , vol.310 , pp. 988
    • Wesseling, A.1    Agoston, S.2
  • 8
    • 0004623544 scopus 로고
    • The experimental pharmacology of Alzheimer's disease and related dementias
    • Meltzer, H. Y., Ed.; Raven Press: New York
    • (a) Mohs, R. C.; Davis, K. L. The experimental pharmacology of Alzheimer's disease and related dementias. In Psychopharmacology: The Third Generation of Progress; Meltzer, H. Y., Ed.; Raven Press: New York, 1987.
    • (1987) Psychopharmacology: The Third Generation of Progress
    • Mohs, R.C.1    Davis, K.L.2
  • 9
    • 0018164085 scopus 로고
    • Influence of choline on amnesia in early Alzheimer's disease
    • (b) Signoret, J. L.; Whitely, A.; Lhermitte, F. Influence of choline on amnesia in early Alzheimer's disease. Lancet 1978, No. 2, 837.
    • (1978) Lancet , Issue.2 , pp. 837
    • Signoret, J.L.1    Whitely, A.2    Lhermitte, F.3
  • 10
    • 0017291039 scopus 로고
    • Brain acetylcholine: Control by dietary choline
    • (c) Cohen, E. I.; Wurtman, R. J. Brain acetylcholine: control by dietary choline. Science 1976, 797, 561-562.
    • (1976) Science , vol.797 , pp. 561-562
    • Cohen, E.I.1    Wurtman, R.J.2
  • 11
    • 0016716456 scopus 로고
    • Increase in rat brain acetyl-choline induced by choline or deanol
    • (d) Hanbrich, D. R.; Wang, P. F. L.; Clody, D. E.; Wedeking, P. W. Increase in rat brain acetyl-choline induced by choline or deanol. Life Sci. 1975, 17, 975-980.
    • (1975) Life Sci. , vol.17 , pp. 975-980
    • Hanbrich, D.R.1    Wang, P.F.L.2    Clody, D.E.3    Wedeking, P.W.4
  • 12
    • 0022899577 scopus 로고
    • Oral tetrahydroaminoacridine in long term treatment of senile dementia, Alzheimer type
    • Summers, W. K.; Majovski, L. V.; Marsh, G. M; Tachiki, K; Kling, A. Oral tetrahydroaminoacridine in long term treatment of senile dementia, Alzheimer type. N. Engl. J. Med. 1986, 375, 1241-1245.
    • (1986) N. Engl. J. Med. , vol.375 , pp. 1241-1245
    • Summers, W.K.1    Majovski, L.V.2    Marsh, G.M.3    Tachiki, K.4    Kling, A.5
  • 13
    • 9844257886 scopus 로고
    • Improved synthesis of aminoacridines, Part IV. Substituted 5-aminoacridines
    • Albert, A.; Gledhill, W. J. Improved synthesis of aminoacridines, Part IV. Substituted 5-aminoacridines. J. Soc. Chem. Ind. 1945, 64, 169-172.
    • (1945) J. Soc. Chem. Ind. , vol.64 , pp. 169-172
    • Albert, A.1    Gledhill, W.J.2
  • 14
    • 0000685381 scopus 로고
    • The pharmacology of some new anticholinesterases
    • Shaw, F. H.; Bentley, G. The pharmacology of some new anticholinesterases. Aust. J. Exp. Biol. Med. Sci. 1953, 31, 573-576.
    • (1953) Aust. J. Exp. Biol. Med. Sci. , vol.31 , pp. 573-576
    • Shaw, F.H.1    Bentley, G.2
  • 15
    • 0000793190 scopus 로고
    • Inhibition of cholinesterases by tetrahydroaminacrin
    • Heilbronn, E. Inhibition of cholinesterases by tetrahydroaminacrin. Acta Chem. Scand. 1961, 15, 1386-1390.
    • (1961) Acta Chem. Scand. , vol.15 , pp. 1386-1390
    • Heilbronn, E.1
  • 16
    • 0015963263 scopus 로고
    • Psychotomimetics as anticholinergic agents. I. 1-Cyclohexy-lpiperidine derivatives: Anticholinesterase activity and antagonistic activity to acetylcholine
    • Maayani, S.; Weinstein, H.; Ben-Zvi, N.; Cohen, S.; Sokolovsky, M. Psychotomimetics as anticholinergic agents. I. 1-Cyclohexy-lpiperidine derivatives: anticholinesterase activity and antagonistic activity to acetylcholine. Biochem. Pharmacol. 1974, 23, 1263-1281.
    • (1974) Biochem. Pharmacol. , vol.23 , pp. 1263-1281
    • Maayani, S.1    Weinstein, H.2    Ben-Zvi, N.3    Cohen, S.4    Sokolovsky, M.5
  • 17
    • 0012682604 scopus 로고    scopus 로고
    • + currents at a cholinergic nerve terminal
    • Giacobini, E., Becker, R., Eds.; Taylor and Francis: New York
    • + currents at a cholinergic nerve terminal. Current Research in Alzheimer Therapy; Giacobini, E., Becker, R., Eds.; Taylor and Francis: New York, pp 191-197.
    • Current Research in Alzheimer Therapy , pp. 191-197
    • Harvey, A.L.1    Rowan, E.G.2
  • 18
    • 0023857396 scopus 로고
    • Further analysis of the neuropharmacological profile of 9-amino-1,2,3,4-tetrahy-droacridine (THA), an alleged drug for the treament of Alzheimer's disease
    • (a) Drukarch, B.; Leysen, J. E.; Stoof, J. C. Further analysis of the neuropharmacological profile of 9-amino-1,2,3,4-tetrahy-droacridine (THA), an alleged drug for the treament of Alzheimer's disease. Life Sci. 1988, 42, 1011-1017.
    • (1988) Life Sci. , vol.42 , pp. 1011-1017
    • Drukarch, B.1    Leysen, J.E.2    Stoof, J.C.3
  • 19
    • 0026646126 scopus 로고
    • Characterisation of dopamine and serotonin uptake inhibitory effects of tetrahydroaminoacridine in rat brain
    • (b) Sokhwinder, J.; Adem, A.; Winblad, B.; Oreland, L. Characterisation of dopamine and serotonin uptake inhibitory effects of tetrahydroaminoacridine in rat brain. Pharmacol. Toxicol. 1992, 71, 213-215.
    • (1992) Pharmacol. Toxicol. , vol.71 , pp. 213-215
    • Sokhwinder, J.1    Adem, A.2    Winblad, B.3    Oreland, L.4
  • 20
    • 0344174664 scopus 로고
    • Enzyme inhibition action of tetrahydroaminacridine and its structural fragments
    • (a) Kaul, P. N. Enzyme inhibition action of tetrahydroaminacridine and its structural fragments. J. Pharm. Pharmacol. 1962, 14, 243-248.
    • (1962) J. Pharm. Pharmacol. , vol.14 , pp. 243-248
    • Kaul, P.N.1
  • 21
    • 0024818025 scopus 로고
    • Correlation of brain levels of 9-amino-1,2,3,4-tetrahydroacridine (THA) with neurochemical and behavioural changes
    • (b) Neilsen, J. A.; Mena, E. E.; Williams, I. H.; Nocerini, M. R.; Liston, D. Correlation of brain levels of 9-amino-1,2,3,4-tetrahydroacridine (THA) with neurochemical and behavioural changes. Eur. J. Pharmacol. 1988, 173. 53-64.
    • (1988) Eur. J. Pharmacol. , vol.173 , pp. 53-64
    • Neilsen, J.A.1    Mena, E.E.2    Williams, I.H.3    Nocerini, M.R.4    Liston, D.5
  • 22
    • 0024801315 scopus 로고
    • Quantitative whole-body autoradiographic determination of tacrine tissue distribution in rats following intravenous or oral dose
    • (c) McNally, W.; Rothom, Young, R.; Brockbrader, H.; Chang, T. Quantitative whole-body autoradiographic determination of tacrine tissue distribution in rats following intravenous or oral dose. Pharm. Res. 1989, 924-930.
    • (1989) Pharm. Res. , pp. 924-930
    • McNally, W.1    Rothom2    Young, R.3    Brockbrader, H.4    Chang, T.5
  • 23
    • 0025074521 scopus 로고
    • Effects of tetrahydro-9-aminoacridine on cortical and hippocampal neurons in the rat
    • Dutar, P.; Bassant, M. H; Lamour, Y. Effects of tetrahydro-9-aminoacridine on cortical and hippocampal neurons in the rat. Brain Res. 1990, 527, 32-40.
    • (1990) Brain Res. , vol.527 , pp. 32-40
    • Dutar, P.1    Bassant, M.H.2    Lamour, Y.3
  • 24
    • 0027989776 scopus 로고
    • Three-dimensional structures of acetyicholinesterase and of its complexes with anticholinesterase agents
    • Sihnan, I.; Harel, M.; Axelsen, P.; Raves, M.; Sussman, J. L. Three-dimensional structures of acetyicholinesterase and of its complexes with anticholinesterase agents. Biochem. Soc. Trans. 1994, 22, 745-749.
    • (1994) Biochem. Soc. Trans. , vol.22 , pp. 745-749
    • Sihnan, I.1    Harel, M.2    Axelsen, P.3    Raves, M.4    Sussman, J.L.5
  • 25
    • 0002753656 scopus 로고
    • A direct synthesis of 4-aminoquinolines
    • Moore, J. A.; Kornreich, L. D. A direct synthesis of 4-aminoquinolines. Tetrahedron. Lett. 1963, 20, 1277-1281.
    • (1963) Tetrahedron. Lett. , vol.20 , pp. 1277-1281
    • Moore, J.A.1    Kornreich, L.D.2
  • 26
    • 9844244858 scopus 로고
    • Benzosuberones: Syntheses, some reaction and formation of benzo[3,4]cyclohepta[1,2-b]pyrrole derivatives
    • (a) da Conceicao, C. M. M.; MacRitchie, J. A.; Middlemiss, D.; Proctor, G. R. Benzosuberones: syntheses, some reaction and formation of benzo[3,4]cyclohepta[1,2-b]pyrrole derivatives. J. Chem. Res. Synop. 1995, 347.
    • (1995) J. Chem. Res. Synop. , vol.347
    • Da Conceicao, C.M.M.1    MacRitchie, J.A.2    Middlemiss, D.3    Proctor, G.R.4
  • 28
    • 33847803678 scopus 로고
    • Olefin synthesis with organic phosphonate carbanions
    • (a) Boutagy, J.; Thomas, R. Olefin synthesis with organic phosphonate carbanions. Chem. Rev. 1974, 74, 87-99.
    • (1974) Chem. Rev. , vol.74 , pp. 87-99
    • Boutagy, J.1    Thomas, R.2
  • 29
    • 0003083944 scopus 로고
    • Synthetic applications of phosphoryl-stabilised anions
    • (b) Wadsworth, W. S., Jr. Synthetic applications of phosphoryl-stabilised anions. Org. React. 1977, 25, 73-253.
    • (1977) Org. React. , vol.25 , pp. 73-253
    • Wadsworth Jr., W.S.1
  • 30
    • 0000531829 scopus 로고
    • The Wittig reaction
    • (c) Maercker, A. The Wittig reaction. Org. React. 1965, 14, 270-490.
    • (1965) Org. React. , vol.14 , pp. 270-490
    • Maercker, A.1
  • 32
    • 84948661389 scopus 로고
    • Uber das Keto-enol gleichgewicht bei cyclischen α-diketonen
    • (a) Schwarzenbach, G.; Wittwer, C. Uber das Keto-enol gleichgewicht bei cyclischen α-diketonen. Helv. Chem. Acta 1947, 30, 663-669.
    • (1947) Helv. Chem. Acta , vol.30 , pp. 663-669
    • Schwarzenbach, G.1    Wittwer, C.2
  • 33
    • 0041323170 scopus 로고
    • The enol structure of 3-methyl-cyclopemane-1,2-dione
    • (b) Bredenberg, J. B. The enol structure of 3-methyl-cyclopemane-1,2-dione. Acta Chem. Scand. 1959, 13, 1733-1736.
    • (1959) Acta Chem. Scand. , vol.13 , pp. 1733-1736
    • Bredenberg, J.B.1
  • 34
    • 9844240237 scopus 로고
    • Formation of methylcyclopentenolone by digestion of spruce wood or galactose with NaOH solutions
    • (c) Enkvis, T.; Alfredsson, B.; Merikallio, M.; Pääkkönen, P.; Järrelä, O. Formation of methylcyclopentenolone by digestion of spruce wood or galactose with NaOH solutions. Acta Chem. Scand. 1954, 8, 51-59.
    • (1954) Acta Chem. Scand. , vol.8 , pp. 51-59
    • Enkvis, T.1    Alfredsson, B.2    Merikallio, M.3    Pääkkönen, P.4    Järrelä, O.5
  • 35
    • 9844222212 scopus 로고
    • The formation of 3(or 5)-methylcyclopent-2-en-2-ol-1-one from acetone
    • (d) Fray, G. I. The formation of 3(or 5)-methylcyclopent-2-en-2-ol-1-one from acetone. Tetrahedron 1961, 14, 161-163.
    • (1961) Tetrahedron , vol.14 , pp. 161-163
    • Fray, G.I.1
  • 36
    • 0013768971 scopus 로고
    • The structures of five cyclic diketones isolated from coffee
    • (e) Gianturco, M. A.; Giammarino, A. S.; Pitcher, R. G. The structures of five cyclic diketones isolated from coffee. Tetrahedron 1963, 19, 2051-2059.
    • (1963) Tetrahedron , vol.19 , pp. 2051-2059
    • Gianturco, M.A.1    Giammarino, A.S.2    Pitcher, R.G.3
  • 37
    • 9844267059 scopus 로고    scopus 로고
    • Merck Index; p 1298, no. 8907.
    • Merck Index , Issue.8907 , pp. 1298
  • 41
    • 0001046633 scopus 로고
    • Cyclization studies in the quinoline series. A new synthesis of 4-aminoquinolines
    • Johnson, W. S.; Woroch, E. L.; Buell, B. H. Cyclization studies in the quinoline series. A new synthesis of 4-aminoquinolines. J. Am. Chem. Soc. 1949, 71, 1901-1905.
    • (1949) J. Am. Chem. Soc. , vol.71 , pp. 1901-1905
    • Johnson, W.S.1    Woroch, E.L.2    Buell, B.H.3
  • 42
    • 37049058490 scopus 로고
    • Azabenzocycloheptenones. III. 2,3,4,5-Tetrahydro-5-oxo-1-toluene-p-sulphonylbenz [b]azepine
    • Proctor, G. R. Azabenzocycloheptenones. III. 2,3,4,5-Tetrahydro-5-oxo-1-toluene-p-sulphonylbenz [b]azepine J. Chem. Soc. 1961, 3989-3996.
    • (1961) J. Chem. Soc. , pp. 3989-3996
    • Proctor, G.R.1
  • 43
    • 0007821975 scopus 로고
    • Prevost, C. Compt. Rend. 1933, 196, 1129; Chem. Abstr. 1933, 27, 3195.
    • (1933) Compt. Rend. , vol.196 , pp. 1129
    • Prevost, C.1
  • 44
    • 3142542576 scopus 로고
    • Prevost, C. Compt. Rend. 1933, 196, 1129; Chem. Abstr. 1933, 27, 3195.
    • (1933) Chem. Abstr. , vol.27 , pp. 3195
  • 45
    • 9844235641 scopus 로고
    • Preparation and some reactions of 1,2,4,5-tetrahydro-1-oxo-3-toluene-p-sulphonylbenz[d]azepine
    • Rehman, M. A.; Proctor, G. R. Preparation and some reactions of 1,2,4,5-tetrahydro-1-oxo-3-toluene-p-sulphonylbenz[d]azepine. J. Chem. Soc. C 1967, 58-61.
    • (1967) J. Chem. Soc. C , pp. 58-61
    • Rehman, M.A.1    Proctor, G.R.2
  • 46
    • 37049139839 scopus 로고
    • Synthesis of 1-benzazocin-6-one derivative by direct cyclisation
    • Proctor, G. R.; Ross, W. I. Synthesis of 1-benzazocin-6-one derivative by direct cyclisation. J. Chem. Soc., Perkin Trans, 1 1972, 885-889.
    • (1972) J. Chem. Soc., Perkin Trans , vol.1 , pp. 885-889
    • Proctor, G.R.1    Ross, W.I.2
  • 48
    • 0021719809 scopus 로고
    • Purification and properties of the membrane-bound form of acetylcholinesterase from chicken brain-evidence for two distinct polypeptide chains
    • Rotundo, R. L. Purification and properties of the membrane-bound form of acetylcholinesterase from chicken brain-evidence for two distinct polypeptide chains. J. Biol. Chem. 1984, 257, 13186.
    • (1984) J. Biol. Chem. , vol.257 , pp. 13186
    • Rotundo, R.L.1
  • 50
    • 0015860717 scopus 로고
    • Structure activity relations for the inhibition of 5-HT [5-hydroxytryptamine] uptake into rat hypothalamic homogenates by serotonin and tryptamine analogues
    • Horn, A. S. Structure activity relations for the inhibition of 5-HT [5-hydroxytryptamine] uptake into rat hypothalamic homogenates by serotonin and tryptamine analogues. J. Neurochem. 1973, 27, 883-888.
    • (1973) J. Neurochem. , vol.27 , pp. 883-888
    • Horn, A.S.1


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