D-Ring substituted rhazinilam analogues : Semisynthesis and evaluation of antitubulin activity

Novel (-)- and (+)-rhazinilam derivatives substituted on the D-ring (compounds 3, 4, 5 and 6) have been prepared from (+)-vincadifformine 7 and (-)-tabersonine and evaluated against the disassembly of microtubules into tubulin. Along with this study, a reproducible 'one pot' semisynthesis...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 1999-12, Vol.7 (12), p.2961-2969
Main Authors: DUPONT, C, GUENARD, D, TCHERTANOV, L, THORET, S, GUERITTE, F
Format: Article
Language:English
Subjects:
Alkaloids - chemical synthesis
Alkaloids - chemistry
Alkaloids - pharmacology
Animals
Antineoplastic agents
Biological and medical sciences
Crystallography, X-Ray
General aspects
In Vitro Techniques
Indolizines
Lactams
Magnetic Resonance Spectroscopy
Medical sciences
Microtubules - drug effects
Models, Molecular
Pharmacology. Drug treatments
Structure-Activity Relationship
Tubulin Modulators
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Summary:Novel (-)- and (+)-rhazinilam derivatives substituted on the D-ring (compounds 3, 4, 5 and 6) have been prepared from (+)-vincadifformine 7 and (-)-tabersonine and evaluated against the disassembly of microtubules into tubulin. Along with this study, a reproducible 'one pot' semisynthesis of (-)-rhazinilam 1 from (+)-1,2-didehydroaspidospermidine 2 was performed allowing the easy preparation of these new compounds.
ISSN:0968-0896
DOI:10.1016/S0968-0896(99)00241-2