Cyclopropanation of Some Alkaloids

New derivatives of natural compounds, galanthamine using in treatment of Alzheimer's disease and antitumor dimer alkaloids vinblastine and vincristine were synthesized. In the course of the reaction between galanthamine and diazomethane in the presence of a catalyst, such as palladium(II) aceta...

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Published inPeriodica polytechnica. Chemical engineering. Vol. 59; no. 1; pp. 3 - 15
Main Authors Keglevich, Péter, Hazai, László, Kalaus, György, Szántay, Csaba
Format Journal Article
LanguageEnglish
Published Budapest Periodica Polytechnica, Budapest University of Technology and Economics 01.01.2015
Subjects
Acetates
Alkaloids
Bonding
Carbon
Derivatives
Dimers
Medical services
Methylene
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Summary:New derivatives of natural compounds, galanthamine using in treatment of Alzheimer's disease and antitumor dimer alkaloids vinblastine and vincristine were synthesized. In the course of the reaction between galanthamine and diazomethane in the presence of a catalyst, such as palladium(II) acetate or copper(I) bromide, methylene insertion into the aromatic ring was observed instead of the expected cyclopropanation of the carbon-carbon double bond. New vindoline derivatives conjugated with amino acid esters were prepared. In Simmons-Smith reaction vinblastine and vincristine cyclopropanated in the carbon carbon double bond in position 14 and 15 of the vindoline monomer were obtained. New dimer alkaloids showed significant inhibiting effects in several tumor cell lines.
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ISSN:0324-5853
1587-3765
DOI:10.3311/PPch.7257