Next Article in Journal
Two New Triterpene Glycosides with Monomethyl Malonate Groups from the Rhizome of Cimifuga foetida L.
Previous Article in Journal
Lianqiaoxinoside B, a Novel Caffeoyl Phenylethanoid Glycoside from Forsythia suspensa
Molecules 2011, 16(7), 5682-5700; doi:10.3390/molecules16075682
Article

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

1,2,*  and 2
Received: 31 May 2011; in revised form: 27 June 2011 / Accepted: 29 June 2011 / Published: 4 July 2011
(This article belongs to the Section Organic Synthesis)
Download PDF [182 KB, uploaded 18 June 2014]
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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Export to BibTeX |
EndNote


MDPI and ACS Style

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.

AMA Style

Saad HA, Moustafa AH. Synthesis and Anticancer Activity of Some New S-Glycosyl and S-Alkyl 1,2,4-Triazinone Derivatives. Molecules. 2011; 16(7):5682-5700.

Chicago/Turabian Style

Saad, Hosam A.; Moustafa, Ahmed H. 2011. "Synthesis and Anticancer Activity of Some New S-Glycosyl and S-Alkyl 1,2,4-Triazinone Derivatives." Molecules 16, no. 7: 5682-5700.


Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
{"cc_re__cc_re__cc_by_3_0": ["-Triazinone Derivatives\">\n\n            <meta name=\"dc.creator\" content=\"Hosam Saad\">\n            <meta name=\"dc.creator\" content=\"Ahmed Moustafa\">\n        \n    <meta name=\"dc.type\" content=\"Article\">\n    <meta name=\"dc.source\" content=\"Molecules 2011, Vol. 16, Pages 5682-5700\">\n    <meta name=\"dc.date\" content=\"2011-07-04\">\n            <meta name =\"dc.identifier\" content=\"10.3390/molecules16075682\">\n    \n    <meta name=\"dc.publisher\" content=\"Molecular Diversity Preservation International\">\n    <meta name=\"dc.rights\" content=\"http://creativecommons.org/licenses/by/3.0/\">\n    <meta name=\"dc.format\" content=\"application/pdf\" >\n    <meta name=\"dc.language\" content=\"en\" >\n\t<meta name=\"dc.description\" content=\"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 a", " \t\t<a href=\"/search?q=S-glycosyl\"><em>S</em>-glycosyl</a>;\t\t\t  \t\t<a href=\"/search?q=S-alkyl triazine\"><em>S</em>-alkyl triazine</a>;\t\t\t  \t\t<a href=\"/search?q=1,2,4-triazinone\">1,2,4-triazinone</a>;\t\t\t  \t\t<a href=\"/search?q=thiadiazolotriazines\">thiadiazolotriazines</a>;\t\t\t  \t\t<a href=\"/search?q=anticancer activities\">anticancer activities</a></span>\n\t\t  </div>\n\t\t\n\n\t\t\n\t\t<div class=\"licenseText\" style=\"padding: 1em; text-align: justify;\">\n\t\t<em>This is an open access article distributed under the <a href=\"http://creativecommons.org/licenses/by/3.0/\" target=\"_blank\">\n\t\tCreative Commons Attribution License</a> which permits unrestricted use, distribution,\n\t\tand reproduction in any medium, provided the original work is properly cited.</em>\n\t\t</div>\n\n   </div><div id=\"tabs-1\" class=\"ui-tabs-panel\">\n<div id=\"loaded\" style=\"display:none\">No</div><div id=framed_div style=\"display: none\"></div>\n  </div>\n\n  <div id=\"tabs-2\" class=\"ui-tabs-panel\">\n\t\t\t      <div id=\"article_stats_div\" style=\"text-align: center; display: none; border: solid #CCCCCC 1px\"><div id=\"artic"], "copyright__copyright__copyright": ["Molecules 2011, 16, 5682-5700.\n\nAMA Style\n\nSaad HA, Moustafa AH. Synthesis and Anticancer Activity of Some New S-Glycosyl and S-Alkyl 1,2,4-Triazinone Derivatives. Molecules. 2011; 16(7):5682-5700.\n\nChicago/Turabian Style\n\nSaad, Hosam A.; Moustafa, Ahmed H. 2011. \"Synthesis and Anticancer Activity of Some New S-Glycosyl and S-Alkyl 1,2,4-Triazinone Derivatives.\" Molecules 16, no. 7: 5682-5700.\n\n\nMolecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert"]}