Synthesis and Anticancer Activity of Some New S-Glycosyl and S-Alkyl 1,2,4-Triazinone Derivatives

Faculty Science Year: 2011
Type of Publication: Article Pages: 5682-5700
Authors: DOI: 10.3390/molecules16075682
Journal: MOLECULES MDPI AG Volume: 16
Research Area: Chemistry ISSN ISI:000293073900028
Keywords : S-glycosyl, S-alkyl triazine, 1, 2, 4-triazinone, thiadiazolotriazines, anticancer activities    
Abstract:
A series of S-glycosyl and S-alkyl derivatives of 4-amino-3-mercapto-6-(2-(2-thienyl)vinyl)-1,2,4-triazin-5(4H)-one (1) were synthesized using different halo compounds such as preacetylated sugar bromide, 4-bromobutylacetate, 2-acetoxyethoxy-methyl bromide, 3-chloropropanol, 1,3-dichloro-2-propanol, epichlorohydrin, allyl bromide, propargyl bromide, phthalic and succinic acids in POCl(3). The structures of the synthesized compounds have been deduced from their elemental analysis and spectral (IR, (1)H-NMR, and (13)C-NMR) data. Some of the synthesized compounds were screened as anticancer agents. Significant anticancer activities were observed in vitro for some members of the series, and compounds 4-Amino-3-(3-hydroxypropylthio)-6-(2-(2-thienyl) vinyl)-1,2,4-triazin-5(4H)-one (12) and 3-(4-Oxo-3-(2-(2-thienyl) vinyl)-4H-{[}1,3,4] thiadiazolo-{[}2,3-c]{[}1,2,4] tr-iazin-7-yl)propanoic acid (18) are active cytotoxic agents against different cancer cell lines.
   
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