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Volumn 36, Issue 26, 1993, Pages 4214-4220

Synthesis and Pharmacological Activity of a Series of Dihydro-1H-pyrrolo[1,2-a]imidazole-2,5(3H,6H)-diones, a Novel Class of Potent Cognition Enhancers

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRROLIDINONE; DIHYDRO 1H PYRROLO[1,2 A]IMIDAZOLE 2,5(3H,6H) DIONE; DIMIRACETAM; NOOTROPIC AGENT; OXIRACETAM; PIRACETAM; SCOPOLAMINE BROMIDE; SODIUM CHLORIDE; UNCLASSIFIED DRUG;

EID: 0027771510     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00078a011     Document Type: Article
Times cited : (72)

References (45)
  • 3
    • 0024788666 scopus 로고
    • The families of cognition enhancers
    • Frostl, W.; Maitre, L. The families of cognition enhancers. Pharmacopsychiatry 1989, 22, 54.
    • (1989) Pharmacopsychiatry , vol.22 , pp. 54
    • Frostl, W.1    Maitre, L.2
  • 4
    • 0025332303 scopus 로고
    • Pharmacology of nootropics and metabolically active compounds in relation to their use in dementia
    • Nicholson, C. D. Pharmacology of nootropics and metabolically active compounds in relation to their use in dementia. Psychopharmacology 1990, 101, 147.
    • (1990) Psychopharmacology , vol.101 , pp. 147
    • Nicholson, C.D.1
  • 6
    • 0024818319 scopus 로고
    • Brain entry and direct pharmacological effects of the nootropic drug oxiracetam
    • Ponzio, F.; Pozzi, O.; Banfi, S.; Dorigotti, L.; Brain entry and direct pharmacological effects of the nootropic drug oxiracetam. Pharmacopsychiatry 1989, 22 Suppl., 111.
    • (1989) Pharmacopsychiatry , vol.22 , pp. 111
    • Ponzio, F.1    Pozzi, O.2    Banfi, S.3    Dorigotti, L.4
  • 7
    • 85022746487 scopus 로고
    • CNS pharmacology and clinical therapeutic effects of oxiracetam
    • Itil, T. M.; Menon, G. M.; Songar, A.; Itil, K. Z.; CNS pharmacology and clinical therapeutic effects of oxiracetam. Pharmacopsychiatry 1989, 22, S70.
    • (1989) Pharmacopsychiatry , vol.22 , pp. S70
    • Itil, T.M.1    Menon, G.M.2    Songar, A.3    Itil, K.Z.4
  • 8
    • 0022499441 scopus 로고
    • Aniracetam augments, and midazolam inhibits, the long-term potentiation in guinea pig hippocampal slices
    • Satoh, M.; Ishihara, K.; Iwama, T.; Takagi, H. Aniracetam augments, and midazolam inhibits, the long-term potentiation in guinea pig hippocampal slices. Neurosci. Lett. 1986, 68, 216.
    • (1986) Neurosci. Lett. , vol.68 , pp. 216
    • Satoh, M.1    Ishihara, K.2    Iwama, T.3    Takagi, H.4
  • 9
    • 0023181845 scopus 로고
    • Interaction between oxiracetam, aniracetam and scopolamine on behavior and brain acetylcholine
    • Spignoli, G.; Pepeu, G. Interaction between oxiracetam, aniracetam and scopolamine on behavior and brain acetylcholine. Pharmacol. Biochem. Behav. 1987, 27, 491.
    • (1987) Pharmacol. Biochem. Behav. , vol.27 , pp. 491
    • Spignoli, G.1    Pepeu, G.2
  • 10
    • 0025039780 scopus 로고
    • Oxiracetam increases the release of endogenous glutamate from depolarized hippocampal slices
    • Marchi, M.; Besana, E.; Raiteri, M. Oxiracetam increases the release of endogenous glutamate from depolarized hippocampal slices. Eur. J. Pharmacol. 1990, 185, 247.
    • (1990) Eur. J. Pharmacol. , vol.185 , pp. 247
    • Marchi, M.1    Besana, E.2    Raiteri, M.3
  • 11
    • 0025067437 scopus 로고
    • Effect of the nootropic drug oxiracetam on field potentials of rat hippocampal slices
    • Pugliese, A. M.; Corradetti, R.; Ballerini, L.; Pepeu, G. Effect of the nootropic drug oxiracetam on field potentials of rat hippocampal slices. Br. J. Pharmacol. 1990, 99, 189.
    • (1990) Br. J. Pharmacol. , vol.99 , pp. 189
    • Pugliese, A.M.1    Corradetti, R.2    Ballerini, L.3    Pepeu, G.4
  • 12
    • 0017395379 scopus 로고
    • Cyclic GABA-GABOB analogues I—Synthesis of new 4-hydroxy-2-pyrrolidinone derivatives
    • Pifferi, G.; Pinza, M. Cyclic GABA-GABOB analogues I—Synthesis of new 4-hydroxy-2-pyrrolidinone derivatives. Farmaco Ed. Sci. 1977, 32, 602.
    • (1977) Farmaco Ed. Sci. , vol.32 , pp. 602
    • Pifferi, G.1    Pinza, M.2
  • 14
    • 0025361145 scopus 로고
    • 3,4-Disubstituted γ-lactam rings as conformationally constrained mimics of peptide derivatives containing aspartic acid or norleucine
    • and references cited therein
    • Garvey, D. S.; May, P. D.; Nadzan, A. M. 3,4-Disubstituted γ-lactam rings as conformationally constrained mimics of peptide derivatives containing aspartic acid or norleucine. J. Org. Chem. 1990, 55, 936 and references cited therein.
    • (1990) J. Org. Chem. , vol.55 , pp. 936
    • Garvey, D.S.1    May, P.D.2    Nadzan, A.M.3
  • 15
    • 4544374521 scopus 로고
    • Pharmacologically active 5-oxo-1-imidazolidineacetamide compounds. U.S. Patent 4,719,222
    • Compound 2 significantly reversed ECS-induced amnesia in mice by 32% at 10 mg/kg ip; oxiracetam's effect was observed only at 60 mg/kg ip (35% reversal)
    • Pinza, M.; Farina, C.; Banfi, S.; Pfeiffer, U. Pharmacologically active 5-oxo-1-imidazolidineacetamide compounds. U.S. Patent 4,719,222; Chem. Abstr. 1987, 107, 59481. Compound 2 significantly reversed ECS-induced amnesia in mice by 32% at 10 mg/kg ip; oxiracetam's effect was observed only at 60 mg/kg ip (35% reversal).
    • (1987) Chem. Abstr. , vol.107 , pp. 59481
    • Pinza, M.1    Farina, C.2    Banfi, S.3    Pfeiffer, U.4
  • 16
    • 4544234268 scopus 로고
    • Nootropic imidazolidinones. U.S. Patent 4,703,0954
    • Compound 3 significantly reversed ECS-induced amnesia in mice by 47% at 10 mg/kg i.p
    • Pinza, M.; Farina, C.; Banfi, S.; Pfeiffer, U. Nootropic imidazolidinones. U.S. Patent 4,703,0954; Chem. Abstr. 1987, 106, 138445. Compound 3 significantly reversed ECS-induced amnesia in mice by 47% at 10 mg/kg i.p.
    • (1987) Chem. Abstr. , vol.106 , pp. 138445
    • Pinza, M.1    Farina, C.2    Banfi, S.3    Pfeiffer, U.4
  • 17
    • 84912847901 scopus 로고
    • Process for the preparation of pyrrolidinone derivatives. U.S. patent 4,797,496
    • Pinza, M.; Pfeiffer, U. Process for the preparation of pyrrolidinone derivatives. U.S. patent 4,797,496; Chem. Abstr. 1986, 104, 68751.
    • (1986) Chem. Abstr. , vol.104 , pp. 68751
    • Pinza, M.1    Pfeiffer, U.2
  • 19
    • 84993879121 scopus 로고
    • An improved synthesis of γ-, δ-, and ϵ-lactams
    • Pellegata, R.; Pinza, M.; Pifferi, G. An improved synthesis of γ-, δ-, and ϵ-lactams. Synthesis 1978, 614.
    • (1978) Synthesis , pp. 614
    • Pellegata, R.1    Pinza, M.2    Pifferi, G.3
  • 22
    • 0023004512 scopus 로고
    • Experimental behavioral studies with oxiracetam on different types of chronic cerebral impairment
    • Banfi, S.; Dorigotti, L.; Experimental behavioral studies with oxiracetam on different types of chronic cerebral impairment. Clin. Neuropharmacol. 1986, 9 (Suppl. 3), S19.
    • (1986) Clin. Neuropharmacol. , vol.9 , pp. S19
    • Banfi, S.1    Dorigotti, L.2
  • 23
    • 0026590195 scopus 로고
    • Behavioral screening for cognition enhancers: from indiscriminate to valid testing
    • Sarter, M.; Hagan, J.; Dudchenko, P.; Behavioral screening for cognition enhancers: from indiscriminate to valid testing: Part 1. Psychopharmacology 1992, 107, 144.
    • (1992) Psychopharmacology , vol.107 , pp. 144
    • Sarter, M.1    Hagan, J.2    Dudchenko, P.3
  • 24
    • 0026575722 scopus 로고
    • Behavioral screening for cognition enhancers: from indiscriminate to valid testing
    • Sarter, M.; Hagan, J.; Dudchenko, P.; Behavioral screening for cognition enhancers: from indiscriminate to valid testing: Part 2. Psychopharmacology 1992, 107, 461.
    • (1992) Psychopharmacology , vol.107 , pp. 461
    • Sarter, M.1    Hagan, J.2    Dudchenko, P.3
  • 25
    • 0020387616 scopus 로고
    • A screening method for substances potentially active on learning and memory
    • Banfi, S.; Cornelli, U.; Fonio, W.; Dorigotti, L. A screening method for substances potentially active on learning and memory. J. Pharmacol. Methods 1982, 8, 255.
    • (1982) J. Pharmacol. Methods , vol.8 , pp. 255
    • Banfi, S.1    Cornelli, U.2    Fonio, W.3    Dorigotti, L.4
  • 27
    • 0021320536 scopus 로고
    • Amnesia-reversal activity of a series of n-[(disubstituted-amino)alkyl]-2-oxo-l-pyrrolidineacetamides, including pramiracetam
    • Butler, D. E.; Nordin, I. C.; L'Italien, Y. J.; Zweisler, L.; Poschel, P. H.; Marriott, J. G. Amnesia-reversal activity of a series of n-[(disubstituted-amino)alkyl]-2-oxo-l-pyrrolidineacetamides, including pramiracetam. J. Med. Chem. 1984, 27, 684.
    • (1984) J. Med. Chem. , vol.27 , pp. 684
    • Butler, D.E.1    Nordin, I.C.2    L'Italien, Y.J.3    Zweisler, L.4    Poschel, P.H.5    Marriott, J.G.6
  • 30
    • 0025695399 scopus 로고
    • The validity of animal models in the search for drugs for the aging brain
    • Pepeu, G.; Marconcini-Pepeu, I.; Casamenti, F.; The validity of animal models in the search for drugs for the aging brain. Drug Des. Delivery 1990, 7, 1.
    • (1990) Drug Des. Delivery , vol.7 , pp. 1
    • Pepeu, G.1    Marconcini-Pepeu, I.2    Casamenti, F.3
  • 31
    • 0024408567 scopus 로고
    • Effects of scopolamine on verbal memory; a retrival or acquisition deficit
    • Rusted, J. M.; Warburton, D. Effects of scopolamine on verbal memory; a retrival or acquisition deficit? Neuropsychobiology 1989, 21, 76.
    • (1989) Neuropsychobiology , vol.21 , pp. 76
    • Rusted, J.M.1    Warburton, D.2
  • 32
    • 0023228040 scopus 로고
    • The use of a scopolamine model to study the nootropic effects of tenilsetam (CAS 977) in man
    • Wesnes, K.; Simpson, P. M.; Kidd, A. The use of a scopolamine model to study the nootropic effects of tenilsetam (CAS 977) in man. Med. Sci. Res. 1987, 15, 1063.
    • (1987) Med. Sci. Res. , vol.15 , pp. 1063
    • Wesnes, K.1    Simpson, P.M.2    Kidd, A.3
  • 33
    • 0019972810 scopus 로고
    • The cholinergic hypothesis of geriatric memory dysfunction
    • Bartus, R. T.; Dean, R. L., III; Beer, B.; Lippa, A. S. The cholinergic hypothesis of geriatric memory dysfunction. Science 1982, 217, 408.
    • (1982) Science , vol.217 , pp. 408
    • Bartus, R.T.1    Dean, R.L.2    Beer, B.3    Lippa, A.S.4
  • 36
    • 0026792734 scopus 로고
    • Effect of four non-cholinergic cognitive enhancers in comparison with tacrine and galanthamine on scopolamine-induced amnesia in rats
    • Chopin, P.; Briley, M. Effect of four non-cholinergic cognitive enhancers in comparison with tacrine and galanthamine on scopolamine-induced amnesia in rats. Psychopharmacology 1992, 106, 26.
    • (1992) Psychopharmacology , vol.106 , pp. 26
    • Chopin, P.1    Briley, M.2
  • 37
    • 85022879814 scopus 로고
    • FDA committee endorses Warner-Lambert's tacrine
    • March 26
    • FDA committee endorses Warner-Lambert's tacrine. Scrip 1993, March 26, 19.
    • (1993) Scrip , pp. 19
  • 38
    • 0014424692 scopus 로고
    • Comprehensive observational assessment: Ia. A systematic quantitative procedure for assessing the behavioral and physiologic state of the mouse
    • Irwin, S. Comprehensive observational assessment: Ia. A systematic quantitative procedure for assessing the behavioral and physiologic state of the mouse. Psychopharmacology (Berlin) 1968, 13, 222.
    • (1968) Psychopharmacology (Berlin) , vol.13 , pp. 222
    • Irwin, S.1
  • 39
    • 0026592972 scopus 로고
    • Oxiracetam antagonizes the disruptive effect of scopolamine on memory in the radial maze
    • Magnani, M.; Pozzi, O.; Biagetti, R.; Banfi, S.; Dorigotti, L.; Oxiracetam antagonizes the disruptive effect of scopolamine on memory in the radial maze. Psychopharmacology 1992, 106, 175.
    • (1992) Psychopharmacology , vol.106 , pp. 175
    • Magnani, M.1    Pozzi, O.2    Biagetti, R.3    Banfi, S.4    Dorigotti, L.5
  • 40
    • 33947342417 scopus 로고
    • A simplified method of preparation of alpha amino acids amides
    • Yang, P. S.; Rising, M. M. A simplified method of preparation of alpha amino acids amides. J. Am. Chem. Soc. 1931, 53, 3183.
    • (1931) J. Am. Chem. Soc. , vol.53 , pp. 3183
    • Yang, P.S.1    Rising, M.M.2
  • 41
    • 0001624667 scopus 로고
    • Specificity of leucine ami-nopeptidase. V. Activation, specificity, and mechanism of action
    • Smith, E. L.; Spackman, D. H. Specificity of leucine ami-nopeptidase. V. Activation, specificity, and mechanism of action. J. Biol. Chem. 1955, 212, 271.
    • (1955) J. Biol. Chem. , vol.212 , pp. 271
    • Smith, E.L.1    Spackman, D.H.2
  • 42
    • 37049087935 scopus 로고
    • Regiochemistry of nucleophilic opening of β-substituted styrene oxides with thiolate anions: model experiments in the synthesis of leukotriene analogues
    • Marples, B. A.; Saint, C. G.; Traynor, J. R. Regiochemistry of nucleophilic opening of β-substituted styrene oxides with thiolate anions: model experiments in the synthesis of leukotriene analogues. J. Chem. Soc. Perkin Trans. 1, 1986, 567.
    • (1986) J. Chem. Soc. Perkin Trans. , vol.1 , pp. 567
    • Marples, B.A.1    Saint, C.G.2    Traynor, J.R.3
  • 44
    • 0014121199 scopus 로고
    • An improved one-trial passive avoidance learning situation
    • Jarwik, M. E.; Kopp, R. An improved one-trial passive avoidance learning situation. Psychol. Rev. 1967, 21, 221.
    • (1967) Psychol. Rev. , vol.21 , pp. 221
    • Jarwik, M.E.1    Kopp, R.2
  • 45
    • 84950435288 scopus 로고
    • A network algorithm for performing Fisher's exact test in r × c contingency tables
    • The software employed was SAS Stat. Rel. 6.3, available from SAS Institute
    • Metha, C. R.; Pathel, N. R. A network algorithm for performing Fisher's exact test in r × c contingency tables. J. Am. Stat. Assoc. 1983, 78, 427. The software employed was SAS Stat. Rel. 6.3, available from SAS Institute.
    • (1983) J. Am. Stat. Assoc. , vol.78 , pp. 427
    • Metha, C.R.1    Pathel, N.R.2


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