Synthesis of n-aminoglycosides derived from alkaloid cytisine, their biological activity and crystal structure of N-(β-D-galactopyranosyl)cytisine

Optimal conditions were found for the synthesis of a number of new N-aminoglycosides of the alkaloid cytisine, using commercially available monosaccharides, namely, D-glucose, D-galactose, D-xylose, and L-arabinose. X-ray structural analysis indicated an absolute β-anomeric configuration of N-(β-D-g...

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Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2010-06, Vol.46 (2), p.240-244
Main Authors: Kulakov, I. V, Nurkenov, O. A, Turdybekov, D. M, Mahmutova, A. S, Ahmetova, S. B, Sejdahmetova, R. B, Turdybekov, K. M
Format: Article
Language:English
Subjects:
alkaloid cytisine
Alkaloids
Chemistry
Chemistry and Materials Science
Crystals
cytotoxic activity
D-galactose
D-xylose, and L-arabinose
Dextrose
Galactose
Glucose
Glucose metabolism
monosaccharides of D-glucose
N-(β-D-galactopyranosyl)cytisine
N-aminoglycosides
Organic Chemistry
Pharmacy
Structure
X-ray structural analysis
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Summary:Optimal conditions were found for the synthesis of a number of new N-aminoglycosides of the alkaloid cytisine, using commercially available monosaccharides, namely, D-glucose, D-galactose, D-xylose, and L-arabinose. X-ray structural analysis indicated an absolute β-anomeric configuration of N-(β-D-galactopyranosyl)cytisine in the crystalline state. The comparative cytotoxicity of cytisine and some of its N-aminoglycosides was determined.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-010-0497-y