Synthesis and studies of acetylthioglycoside conjugates of 4-chloro-1,2-dithiole-3-thione as potential antitumor agents

Nucleophilic substitution of a chlorine atom in 4,5 dichloro-1,2-dithiole-3-thione with per- O -acetyl-1-mercaptho derivatives of d -glucose, d -galactose, d -mannose, d -xylose, l -arabinose, and d -maltose gave six new acetylthioglycoside conjugates of 4-chloro-1,2-dithiole-3-thione. These thiogly...

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Bibliographic Details
Published in:Russian chemical bulletin 2021-03, Vol.70 (3), p.573-579
Main Authors: Fedorov, S. N., Kuzmich, A. S., Sabutskii, Yu. E., Guzii, A. G., Popov, R. S., Ogurtsov, V. A., Rakitin, O. A., Polonik, S. G.
Format: Article
Language:English
Subjects:
Anticancer properties
Arabinose
Cancer
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Chlorine
Conjugates
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Galactose
Inorganic Chemistry
Leukemia
Maltose
Mannose
Organic Chemistry
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Summary:Nucleophilic substitution of a chlorine atom in 4,5 dichloro-1,2-dithiole-3-thione with per- O -acetyl-1-mercaptho derivatives of d -glucose, d -galactose, d -mannose, d -xylose, l -arabinose, and d -maltose gave six new acetylthioglycoside conjugates of 4-chloro-1,2-dithiole-3-thione. These thioglycosides were shown to possess cancer preventive activity on the models of JB6 Cl41 P + mouse epidermal cells and THP-1 human leukemia cells in soft agar, as well as to inhibit the AP-1-dependent transcriptional activity in JB6 Cl41 luc-AP-1 cells, which suggests the possibility of using the new compounds as potential cancer preventive drugs.
ISSN:1066-5285
1573-9171
DOI:10.1007/s11172-021-3127-1