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

• Published in: Russian chemical bulletin Vol. 70; no. 3; pp. 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: Journal Article
• Language: English
• Published: New York Springer US 01-03-2021; Springer Nature B.V
• Subjects: Anticancer properties; Arabinose; Cancer; Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Chlorine; Conjugates; Full Articles; Galactose; Inorganic Chemistry; Leukemia; Maltose; Mannose; Organic Chemistry; acetylthioglycosides; inhibition of nuclear factor AP-1; cancer preventive effect; 4,5-dichloro-1,2-dithiole-3-thione; sulfur-containing heterocycles; nucleophilic substitution
• ISSN: 1066-5285; 1573-9171
• DOI: 10.1007/s11172-021-3127-1

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.