Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogs and their N-oxides. Potential antitumor agents

(-)- and (+)-trachelanthic and (-)- and (+)-viridifloric acids were synthesized and their isopropylidene derivatives were regiospecifically coupled, at C-9, with (-)-retronecine obtained by hydrolysis of monocrotaline, isolated from Crotalaria spectabilis. Hydrolysis, followed by oxidation, led to t...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1985-06, Vol.28 (6), p.687-694
Main Authors: Zalkow, Leon H, Glinski, Jan A, Gelbaum, Leslie T, Fleischmann, Thomas J, McGowan, Laureen S, Gordon, Maureen M
Format: Article
Language:English
Subjects:
Animals
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - pharmacology
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Leukemia P388 - drug therapy
Magnetic Resonance Spectroscopy
Mice
Organic chemistry
Preparations and properties
Pyrrolizidine Alkaloids - chemical synthesis
Pyrrolizidine Alkaloids - pharmacology
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Summary:(-)- and (+)-trachelanthic and (-)- and (+)-viridifloric acids were synthesized and their isopropylidene derivatives were regiospecifically coupled, at C-9, with (-)-retronecine obtained by hydrolysis of monocrotaline, isolated from Crotalaria spectabilis. Hydrolysis, followed by oxidation, led to the N-oxides of indicine, intermedine, lycopsamine, and the new nonnatural product, respectively. Each of these analogues was screened in the P388 lymphocytic leukemia system at the same time as indicine N-oxide, and the results were compared. Other related analogues were prepared and similarly screened and the results compared with those from indicine N-oxide.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00383a001