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    The synthesis of a functionalized derivative of ellipticine : 5-(hydroxymethyl)-9-methoxy11-methyl-6h-pyrido[4,3-b] carbazole n-methyl carbamate

    Author
    McComb, Todd
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    177970_thesis.pdf (1.114Mb)
    Other Contributors
    Archer, Sydney;
    Date Issued
    1989-05
    Subject
    Chemistry
    Degree
    MS;
    Terms of Use
    This electronic version is a licensed copy owned by Rensselaer Polytechnic Institute, Troy, NY. Copyright of original work retained by author.;
    Metadata
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    URI
    https://hdl.handle.net/20.500.13015/1878
    Abstract
    The synthesis of 11 was examined towards the goal of preparing sufficient quantities for biological testing. The preliminary results of its activity against some human cancer tumor cells are presented.; The acid 1 was treated with thionyl chloride and then dimethyl amine to give the amide 2 in excellent yield. The reduction of this amide with lithium aluminum hydride followed by treatment with methyl iodide gave a good yield of the methiodide 1. The displacement of trimethylamine from 1 by heating it with potassium cyanide gave the nitrile 4 in low yield. Methanolysis of 4 cleanly gave the ester 5. The acid catalyzed condensation of 5 with 3-acetylpyridine followed by quaternization at the pyridine nitrogen with 4-nitrobenzyl bromide gave the salt 7 in good yield. The intermolecular ring closure that converted 7 into 8 occurred in nearly quantitative yield. The dequaternization of 8 by heating with tributylphosphine gave the ester 9 in an acceptable yield. Reduction of 9 with lithium aluminum hydride gave an excellent yield of the alcohol 10. Treatment of 10 with 4-dimethylaminopyridine and excess methyl isocyanate gave the title compound in an acceptable yield.;
    Description
    May 1989; School of Science
    Department
    Dept. of Chemistry;
    Publisher
    Rensselaer Polytechnic Institute, Troy, NY
    Relationships
    Rensselaer Theses and Dissertations Online Collection;
    Access
    Restricted to current Rensselaer faculty, staff and students. Access inquiries may be directed to the Rensselaer Libraries.;
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    • RPI Theses Online (Complete)

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