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Volumn 39, Issue 25, 1996, Pages 4997-5004

Cyclic nitrone free radical traps: Isolation, identification, and synthesis of 3,3-dimethyl-3,4-dihydroisoquinolin-4-ol N-oxide, a metabolite with reduced side effects

Author keywords

[No Author keywords available]

Indexed keywords

3,3 DIMETHYL 3,4 DIHYDROISOQUINOLIN 4 OL N OXIDE; ANTIOXIDANT; FREE RADICAL; N TERT BUTYL ALPHA PHENYLNITRONE; UNCLASSIFIED DRUG;

EID: 10544240359     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960244n     Document Type: Article
Times cited : (21)

References (29)
  • 1
    • 0025314685 scopus 로고
    • Role of Oxygen Free Radicals in Carcinogenesis and Brain Ischemia
    • (a) Floyd, R. A. Role of Oxygen Free Radicals in Carcinogenesis and Brain Ischemia. FASEB J. 1990, 4, 2587-2597.
    • (1990) FASEB J. , vol.4 , pp. 2587-2597
    • Floyd, R.A.1
  • 2
    • 0024785709 scopus 로고
    • Oxygen Radicals in CNS Damage
    • (b) Kontos, H. A. Oxygen Radicals in CNS Damage. Chem-Biol. Int. 1989, 72, 229-255.
    • (1989) Chem-Biol. Int. , vol.72 , pp. 229-255
    • Kontos, H.A.1
  • 3
    • 0025237287 scopus 로고
    • Protective Effect of α-Tocopherol on Ischemic Neuronal Damage in the Gerbil Hippocampus
    • Hara, H.; Kato, H.; Kogure, K. Protective Effect of α-Tocopherol on Ischemic Neuronal Damage in the Gerbil Hippocampus. Brain Res. 1990, 510, 335-338.
    • (1990) Brain Res. , vol.510 , pp. 335-338
    • Hara, H.1    Kato, H.2    Kogure, K.3
  • 5
    • 0029933374 scopus 로고    scopus 로고
    • Synthesis of Benzazepine-based Nitrones as Radical Traps
    • (b) Bernotas, R. C.; Adams, G.; Carr, A. A. Synthesis of Benzazepine-based Nitrones as Radical Traps. Tetrahedron 1996, 52, 6519-6526.
    • (1996) Tetrahedron , vol.52 , pp. 6519-6526
    • Bernotas, R.C.1    Adams, G.2    Carr, A.A.3
  • 6
    • 0028104414 scopus 로고
    • Multiple Mechanisms for Inhibition of Low Density Lipoprotein Oxidation by Novel Cyclic Nitrone Spin Traps
    • (c) Thomas, C. E.; Ohlweiler, D. F.; Kalyanaraman, B. Multiple Mechanisms for Inhibition of Low Density Lipoprotein Oxidation by Novel Cyclic Nitrone Spin Traps. J. Biol. Chem. 1994, 269 (45), 28055-28061.
    • (1994) J. Biol. Chem. , vol.269 , Issue.45 , pp. 28055-28061
    • Thomas, C.E.1    Ohlweiler, D.F.2    Kalyanaraman, B.3
  • 7
    • 0028625523 scopus 로고
    • In Vitro and in Vivo Activity of a Novel Series of Radical Trapping Agents in Model Systems of CNS Oxidative Damage
    • (a) Thomas, C. E.; Carney, J. M.; Bernotas, R. C.; Hay, D. A.; Carr, A. A. In Vitro and In Vivo Activity of a Novel Series of Radical Trapping Agents in Model Systems of CNS Oxidative Damage. Ann. N.Y. Acad. Sci. 1994, 738, 243-249.
    • (1994) Ann. N.Y. Acad. Sci. , vol.738 , pp. 243-249
    • Thomas, C.E.1    Carney, J.M.2    Bernotas, R.C.3    Hay, D.A.4    Carr, A.A.5
  • 8
    • 0025309904 scopus 로고
    • Oxidative Damage to Brain Proteins, Loss of Glutamine Synthetase Activity, and Production of Free Radicals during Ischemia/Reperfusion-Induced Injury to Gerbil Brain
    • (b) Oliver, C. N.; Starke-Reed, P. E.; Stadtman, E. R.; Liu, G. J.; Carney, J. M.; Floyd, R. A. Oxidative Damage to Brain Proteins, Loss of Glutamine Synthetase Activity, and Production of Free Radicals During Ischemia/Reperfusion-Induced Injury to Gerbil Brain. Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 5144-5147.
    • (1990) Proc. Natl. Acad. Sci. U.S.A. , vol.87 , pp. 5144-5147
    • Oliver, C.N.1    Starke-Reed, P.E.2    Stadtman, E.R.3    Liu, G.J.4    Carney, J.M.5    Floyd, R.A.6
  • 9
    • 0026522028 scopus 로고
    • Neuroprotective Effects of Phenyl-t-butyl-nitrone in Gerbil Global Brain Ischemia and in Cultured Rat Cerebellar Neurons
    • and references cited therein
    • (c) Yue, T.-L.; Gu, J.-L.; Lysko, P. G.; Cheng, H.-Y.; Barone, F. C.; Feuerstein, G. Neuroprotective Effects of Phenyl-t-butyl-nitrone in Gerbil Global Brain Ischemia and in Cultured Rat Cerebellar Neurons. Brain Res. 1992, 574, 193-197 and references cited therein.
    • (1992) Brain Res. , vol.574 , pp. 193-197
    • Yue, T.-L.1    Gu, J.-L.2    Lysko, P.G.3    Cheng, H.-Y.4    Barone, F.C.5    Feuerstein, G.6
  • 10
    • 0028181531 scopus 로고
    • α-Phenyl-tert-butyl Nitrone Reduces Cortical Infarct and Edema in Rats Subjected to Focal Ischemia
    • Cao, X.; Phillis, J. W. α-Phenyl-tert-butyl Nitrone Reduces Cortical Infarct and Edema in Rats Subjected to Focal Ischemia. Brain Res. 1994, 644, 267-292.
    • (1994) Brain Res. , vol.644 , pp. 267-292
    • Cao, X.1    Phillis, J.W.2
  • 11
    • 0027937751 scopus 로고
    • Delayed Treatment with the Spin Trap α-Phenyl-N-tert-butyl Nitrone (PBN) Reduces Infarct Size Following Transient Middle Cerebral Artery Occlusion in Rats
    • Zhao, Q.; Pahlmark, K.; Smith, M.-L.; Siesjo, B. K. Delayed Treatment with the Spin Trap α-Phenyl-N-tert-butyl Nitrone (PBN) Reduces Infarct Size Following Transient Middle Cerebral Artery Occlusion in Rats. Acta Physiol. Scand. 1994, 152, 349-350.
    • (1994) Acta Physiol. Scand. , vol.152 , pp. 349-350
    • Zhao, Q.1    Pahlmark, K.2    Smith, M.-L.3    Siesjo, B.K.4
  • 13
    • 10544247944 scopus 로고    scopus 로고
    • Unpublished results
    • Unpublished results.
  • 14
    • 0015491739 scopus 로고
    • Reductive Synthesis of α,α-Dimethylphenethylamine
    • Marquard, F.-H.; Edwards, S. Reductive Synthesis of α,α-Dimethylphenethylamine. J. Org. Chem. 1972, 37, 1861-1863.
    • (1972) J. Org. Chem. , vol.37 , pp. 1861-1863
    • Marquard, F.-H.1    Edwards, S.2
  • 15
    • 0003199590 scopus 로고
    • 2-Methyl-2-nitrosopropane and its Dimer
    • Wiley: New York
    • Calder, A.; Forrester, A. B.; Hepburn, S. P. 2-Methyl-2-nitrosopropane and its Dimer. Organic Syntheses; Wiley: New York, 1988; Collect. Vol. VI, pp 803-806.
    • (1988) Organic Syntheses , vol.6 , pp. 803-806
    • Calder, A.1    Forrester, A.B.2    Hepburn, S.P.3
  • 16
    • 0001229573 scopus 로고
    • Synthesis and Characterization of Phenyl-Substituted C-Phenyl-N-tert-butylnitrones and some of Their Radical Adducts
    • Treatment of 4a with Zn/HOAc, known conditions for intermolecular reactions of aldehydes with nitro compounds to give nitrones (Hinton, R. D.; Janzen, E. G. Synthesis and Characterization of Phenyl-Substituted C-Phenyl-N-tert-butylnitrones and some of Their Radical Adducts. J. Org. Chem. 1992, 57, 2646-2651), failed to afford 2.
    • (1992) J. Org. Chem. , vol.57 , pp. 2646-2651
    • Hinton, R.D.1    Janzen, E.G.2
  • 17
    • 10544237831 scopus 로고    scopus 로고
    • note
    • 3 under different conditions. These spectra, and a spectrum of the isolated metabolite 2 for comparison, are included in the Supporting Information. Similar variations have also been observed for the parent compound 1. This is in fact a very common phenomenon that can be observed for many compounds containing basic functionality which can be protonated and can engage in intra- or intermolecular tautomeric equilibria.
  • 18
    • 32744459401 scopus 로고
    • Oxidation of Alcohols by "Activated" Dimethyl Sulfoxide. A Preparative, Steric and Mechanistic Study
    • Omura, K.; Swern, D. Oxidation of Alcohols by "Activated" Dimethyl Sulfoxide. A Preparative, Steric and Mechanistic Study. Tetrahedron 1978, 34, 1651-1660.
    • (1978) Tetrahedron , vol.34 , pp. 1651-1660
    • Omura, K.1    Swern, D.2
  • 19
    • 0000886888 scopus 로고
    • Chemistry of Oxaziridines. 9. Synthesis of 2-Sulfonyl-and 2-Sulfamyloxaziridines Using Potassium Peroxymonosulfate (Oxone)
    • This is the same procedure used to prepare Davis' oxaziridine. See: Davis, F. A.; Chattopadhyay, S.; Towson, J. C.; Lal, S.; Reddy, T. Chemistry of Oxaziridines. 9. Synthesis of 2-Sulfonyl-and 2-Sulfamyloxaziridines Using Potassium Peroxymonosulfate (Oxone). J. Org. Chem. 1988, 53, 2087-2089.
    • (1988) J. Org. Chem. , vol.53 , pp. 2087-2089
    • Davis, F.A.1    Chattopadhyay, S.2    Towson, J.C.3    Lal, S.4    Reddy, T.5
  • 20
    • 0013514805 scopus 로고
    • Peracid Oxidation of Imines. Kinetics and Mechanism of Competitive Formation of Nitrones and Oxaziranes from Cyclic and Acyclic Imines
    • (a) Ogata, Y.; Sawaki, Y. Peracid Oxidation of Imines. Kinetics and Mechanism of Competitive Formation of Nitrones and Oxaziranes from Cyclic and Acyclic Imines. J. Am. Chem. Soc. 1973, 95, 4692-4698.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 4692-4698
    • Ogata, Y.1    Sawaki, Y.2
  • 21
    • 0008561819 scopus 로고
    • A Formal Synthesis of Aspartame via the Oxaziridine-Amide Rearrangement
    • (b) For a UV light-promoted isomerization of oxaziridines to amides, see Duhamel, P.; Goument, B.; Plaquevent, J.-C. A Formal Synthesis of Aspartame via the Oxaziridine-Amide Rearrangement. Tetrahedron Lett. 1987, 28, 2595-2596.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 2595-2596
    • Duhamel, P.1    Goument, B.2    Plaquevent, J.-C.3
  • 22
    • 0023017975 scopus 로고
    • Determination of Hydrophobic Parameters by Reversed-Phase Liquid Chromatography: Theory, Experimental Techniques, and Application in Studies on Quantitative Structure-Activity Relationships
    • 3 Receptor Antagonists by Reversed-Phase High-Performance Liquid Chromatography. J. Chromatogr. A 1994, 667, 29-35.
    • (1986) J. Chromatogr. , vol.373 , pp. 191-225
    • Braumann, T.1
  • 23
    • 0029012036 scopus 로고
    • Bioavailability Estimation by Reversed-Phase Liquid Chromatography: High Bonding Density C-18 Phases for Modeling Biopartitioning Processes
    • 3 Receptor Antagonists by Reversed-Phase High-Performance Liquid Chromatography. J. Chromatogr. A 1994, 667, 29-35.
    • (1995) Anal. Chem. , vol.67 , pp. 48-57
    • Hsieh, M.M.1    Dorsey, J.G.2
  • 24
    • 0028344955 scopus 로고
    • 3 Receptor Antagonists by Reversed-Phase High-Performance Liquid Chromatography
    • 3 Receptor Antagonists by Reversed-Phase High-Performance Liquid Chromatography. J. Chromatogr. A 1994, 667, 29-35.
    • (1994) J. Chromatogr. A , vol.667 , pp. 29-35
    • Kugel, C.1    Heintzelmann, B.2    Wagner, J.3
  • 25
    • 0026776769 scopus 로고
    • Ascorbate and Phenolic Antioxidant Interactions in Prevention of Liposomal Oxidation
    • Thomas, C. E.; McLean, L. R.; Parker, R. A.; Ohlweiler, D. F. Ascorbate and Phenolic Antioxidant Interactions in Prevention of Liposomal Oxidation. Lipids 1992, 27, 543-550.
    • (1992) Lipids , vol.27 , pp. 543-550
    • Thomas, C.E.1    McLean, L.R.2    Parker, R.A.3    Ohlweiler, D.F.4
  • 26
    • 0025045031 scopus 로고
    • HPLC Procedure for the Pharmacokinetic Study of the Spin-Trapping Agent, α-Phenyl-N-tert-Butyl Nitrone (PBN)
    • For brain penetrability of PBN, see: Chen, G.; Griffin M.; Poyer, J. L.; McCay, P. B. HPLC Procedure for the Pharmacokinetic Study of the Spin-Trapping Agent, α-Phenyl-N-tert-Butyl Nitrone (PBN). Free Radical Biol. Med. 1990, 9, 93-98.
    • (1990) Free Radical Biol. Med. , vol.9 , pp. 93-98
    • Chen, G.1    Griffin, M.2    Poyer, J.L.3    McCay, P.B.4
  • 29
    • 10544228700 scopus 로고    scopus 로고
    • note
    • Although this procedure is ostensibly the same as that given for the synthesis of hydroxylamine 5c, it was carried out in a different laboratory and on several occasions gave mainly the amino compound 9c described here. Some of this amine (9c) was formed in the preparation of 5c described above as well, but it was not isolated.


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