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Molecules 2011, 16(7), 5682-5700; doi:10.3390/molecules16075682

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

1
Department of Chemistry, Faculty of Science, Taif University, Taif, 21974, Kingdom of Saudi Arabia
2
Department of Chemistry, Faculty of Science, Zagazig University, Zagazig, 44511, Egypt
*
Author to whom correspondence should be addressed.
Received: 31 May 2011 / Revised: 27 June 2011 / Accepted: 29 June 2011 / Published: 4 July 2011
(This article belongs to the Section Organic Synthesis)
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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 POCl3. The structures of the synthesized compounds have been deduced from their elemental analysis and spectral (IR, 1H-NMR, and 13C-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.
Keywords: S-glycosyl; S-alkyl triazine; 1,2,4-triazinone; thiadiazolotriazines; anticancer activities S-glycosyl; S-alkyl triazine; 1,2,4-triazinone; thiadiazolotriazines; anticancer activities
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Saad, H.A.; Moustafa, A.H. Synthesis and Anticancer Activity of Some New S-Glycosyl and S-Alkyl 1,2,4-Triazinone Derivatives. Molecules 2011, 16, 5682-5700.

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