SYNTHESIS OF TIOSOLFOESTERS WITH S-TRIAZINE FRAGMENT

2018;
: 98-104
1
Lviv Polytechnic National University
2
Lviv Polytechnic National University
3
Lviv Polytechnic National University
4
Lviv Polytechnic National University
5
Lviv Polytechnic National University

Cyanuric chloride is a valuable starting agent for the direct obtaining of highly structured molecules. The substitution of chlorine atoms in the molecule of cyanuric chloride by various pharmacophores’ fragments provides the obtaining a number of 1,3,5-triazine derivatives, among which the promising biologically active substances showing antimicrobial, anticancer, antimalarial and antiviral activity were detected.

Derivatives of thiosulfonic acids are very interesting because thiosulfoesters are structural analogues of natural antibacterial substances. It is known that synthetic esters of thiosulfoacids possess the biological activity, which often exceeds the efficiency of natural analogues. Most of them are offered as medicines, preservatives of fruit and vegetables, effective remedies for plant protection, growth regulators, biocidal additives, insecticides and radioprotector. In addition, esters of thiosulfoacid are effective sulfenilating and sulfonylating reagents in organic synthesis, and valuable objects for solving complex issues of molecular biology and biochemistry.

Taking into account the wide range of possible practical applications of both thiosulphoesters and 1,3,5-triazines, this work proposes the ways of combining these "preferred structures" in one molecule, since this opens up prospects for the search for new biologically active compounds (biocides, fungicides, pesticides, medicinal substances).

The interaction of 2,4,6-trichloro-1,3,5-triazine with potassium and sodium salts of aromatic thiosulfonic acids under different temperature conditions was determined. It has been shown that this interaction occurs with the formation of products of mono- and di-substitution of chlorine atoms of cyanuric chloride in various ratios in all investigated cases.

 The new objects (4,6-dichloro-1,3,5-triazine thiosulfonester, 6-chloro-1,3,5-triazine and isocyanuric dithiosulfoester) were added to the combinatorial library of thiosulfoesters with the sim-triazine fragment for the further search the biologically active compounds Structure and characteristics of synthesized compounds have been confirmed by IR, 1H NMR spectroscopy, elemental analysis and by TLC.

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