• Title/Summary/Keyword: Iminium ion

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Metabolism-Dependent Cavalent Binding of $S(-)-^3H-Nicotine$ to Lung Microsomes in Vitro

  • Kim, Bong-Hee;Shingenaga, Mark-K.
    • Archives of Pharmacal Research
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    • v.16 no.2
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    • pp.89-93
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    • 1993
  • Incubation of $S(-)-^3H$-nicotine with rabbit lung microsomes in the presence of dioxygen and NADPH results in the formation of metabolities that bind covalently to microsomal macro-molecules. The addition of cytochrome P-450 monooxygenase inhibitors, $\alpha$-methylbenzyl ami-nobenzotriazole and aroclor 1260, inhibited both (S)-nicotine metabolism and covalent binding. The relative rates of oxidation of nicotine $\Delta^{1',5'}$ iminium ion to continine indicates that lung $100,000\times{g}$ supematant catalyzed this oxidation approximately 18 times slower than that of liver system based on mg of protein, and increased covalent interactions. Since than that of liver system based on mg of protein, nd increased covalent interactions. Since the activity of lung iminium oxidase appears much lowr than the liver, it is tempting to speculate that localized concentrations of nicotine $\Delta^{1',5'}$ iminium ion in the lung will survive for a longer period of time. These results support that cytochrome P-450 catalyzed oxidation of nicotine leads to the formation of reactive nad electrophilic intemediates capable of chemical interactions with biomacromolecules.

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Ring Opening of Pyrolidine and Formation of N-Protected Amino Ketones; Synthesis of 5-Amino-2-pentanone Derivatives (피롤리딘의 개환과 N-프로텍티드 아미노 케톤의 형성; 5-아미노-2-펜타논 유도체의 합성)

  • Park, Myung-Sook
    • YAKHAK HOEJI
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    • v.40 no.3
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    • pp.300-305
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    • 1996
  • The base-induced elimination of N-protected 2-(bromomethyl)pyrrolidines 12a-c with KHMDS in THF at -78$^{\circ}C$ for 1h gave exocyclic enamines 13a-c. The acidic catalyzed pr otonation on ${\beta}$-carbon atom of 2-(methylene)pyrrolidines 13a-c with $H_3PO_4$ formed endocyclic N-iminium intermediates 14(or 15). Nucleophilic attack of alpha-carbon atom and hydrolysis of N-iminium ion gave carbocationic adduct (aminoalcohol) 16 from which 5-amino-2-pentanones 17a-c were formed after deprotonation.

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The study on the spectroscopic and electrical properties of Azomethine compounds (Azomethine계 화합물의 분광학적 특성과 전기적 특성에 관한 연구)

  • Baek, Dae-Jin;Oh, Won-Chun;Ko, Young-Shin
    • Analytical Science and Technology
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    • v.8 no.3
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    • pp.249-258
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    • 1995
  • The polymers, polyazine, polyazomethine ( I ) and polyazomethine ( II ) were prepared by the condensation of p-benzoquinone with hydrazine hydrate, p-phenylenediamine and diaminomaleonitrile in DMSO, respectively. The IR spectra of these polymers showed a characteristic peak of schiff base (-C=N-) at about $1600cm^{-1}$. These polymers dissolved in concentrated sulfuric acid showed UV/VIS absorption near 300nm indicatiog the presence of iminium ion(>$C\limits^{\small\oplus}=NH-$). Another UV/VIS absorption band in the region of 350~415nm was shown presumably due to the charge transfer transition in the molecule. The electrical conductivities of polyazine, polyazomethine ( I ) and ( II ) were measured. The self-electrical conductivity of these was found to be about $10^{-14}{\sim}10^{-11}{\Omega}^{-1}cm^{-1}$ and these polymers doped with $I_2$ showed the maximum conductivity of about $10^{-2}{\Omega}^{-1}cm^{-1}$.

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