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Paper | Regular issue | Vol 81, No. 1, 2010, pp.91-115
Published online, 6th November, 2009
DOI: 10.3987/COM-09-11839
The Synthesis of Novel 2,4,6-Trisubstituted 1,3,5-Triazines: A Search for Potential MurF Enzyme Inhibitors

Izidor Sosič, Bogdan Štefane,* Andreja Kovač, Samo Turk, Didier Blanot, and Stanislav Gobec*

*Faculty of Chemistry and Chemical Technology, University of Ljubljana, Askerceva 5, 1000 Ljubljana, Slovenia


A series of new 2,4,6-trisubstituted 1,3,5-triazines, possessing a variety of substituents (–OH, –SH, –OMe, –Cl, –HNR, –SR and amino acid moieties), were synthesized and evaluated for the inhibition of the bacterial peptidoglycan biosynthesis enzyme MurF. Ethoxycarbonyl isothiocyanate successfully reacted with a variety of amidines, enabling an approach to 6-substituted-4-thioxo-1,3,5-triazin-2-ones. Also, a representative set of 2-thio-, 2-amino-, and 2-oxo-substituted 1,3,5-triazines was synthesized by the SNAr reaction, employing 2,4,6-trichloro-1,3,5-triazine and 2-chloro-4,6-dimethoxy-1,3,5-triazine as the starting materials. One compound displayed notable inhibitory activity against MurF from Escherichia coli.