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.
Highlights
The chemistry and diverse applications of heterocyclic glycosyl derivatives have received much attention due to their pronounced biological activity. 6-Aza analogues of the naturally occurring nucleic acids components represent isosteres with the C-6 carbon atom of the pyrimidine nucleoside base being replaced by nitrogen [1]
The 1,2,4-triazine moiety has attracted the attention of chemists because many 1,2,4-triazines are biologically active [17,18,19,20,21,22] and are used in medicine, especially as anti AIDS, anticancer [23,24], and antitubercular agents [25], for their anti-anxiety and anti-inflammatory activities [26,27], as well as in agriculture [28,29,30,31]
For the above reasons we sought to synthesize a series of S-glycosyl and S-alkyl of 4-amino-3mercapto-6-(2-(2-thienyl)vinyl)-1,2,4-triazin-5(4H)-one (1) [32] which should combine all the above benefits in one target and to test the anticancer activity of these synthesized compounds against a panel of human cell lines including hepatocellular carcinoma (Hep-G2), colon carcinoma (HCT-116), and histiocytic lymphoma and breast adenocarcinoma (MCF-7) (ATCC, VA, USA)
Summary
The chemistry and diverse applications of heterocyclic glycosyl derivatives have received much attention due to their pronounced biological activity. 6-Aza analogues of the naturally occurring nucleic acids components represent isosteres with the C-6 carbon atom of the pyrimidine nucleoside base being replaced by nitrogen [1]. 6-Aza analogues of the naturally occurring nucleic acids components represent isosteres with the C-6 carbon atom of the pyrimidine nucleoside base being replaced by nitrogen [1] They became attractive to scientists after it was discovered that. The 1,2,4-triazine moiety has attracted the attention of chemists because many 1,2,4-triazines are biologically active [17,18,19,20,21,22] and are used in medicine, especially as anti AIDS, anticancer [23,24], and antitubercular agents [25], for their anti-anxiety and anti-inflammatory activities [26,27], as well as in agriculture [28,29,30,31]
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