The dissertation is devoted to the development of effective ways of synthesis of 9,10-anthracenedione triazene, the study of their chemical properties and biological activity. In order to produce triazenes containing anthraсendions moiety, an effective preparative new method for the synthesis of triazenes in the 9,10-anthracendiones was developed - by diazotization of aminanthracendiones and the N-azo combination with aliphatic, aromatic and heterocycenic amines has been, which is confirmed by the Ukrainian patent .
The interaction of anthracentriazens with compounds containing the active methylene group was investigated in order to search for new potentially biologically active compounds with an anthracendione moiety and to determine the reactivity of the triazines. 1-(morpholinodiazenyl)-anthracene-9,10-dione was selected as anthracentriazene, and classical CH-acids were selected as compounds with active methylene groups. The likely mechanism of this process is proposed.
In order to increase the biological activity, the introduction into the molecule of pharmacophore groups by the interaction of halogenanthracenediazonium chlorides with amines: D, L-tyrosine, its methyl ester and streptocide. The resulting [9,10-anthracendion-1(2)-yl]- and (4-bromo-2-carboxyl-9,10-anthracendion-1-yl) phosphonic acids and their ammonium salts are convenient intermediates for subsequent syntheses of biologically active compounds and the process of synthesis of these acids is investigated.
The 35 previously described novel compounds were synthesized, the structure and purity of which were confirmed by 1H, 13C NMR, UV, IR, mass spectrometry and elemental analysis.
The biological activity of the synthesized novel compounds was investigated in silico using the web resources PASS Online, Antiviral Compound Predictiction (AVCpred), and SAR and QSAR. The relationship between the structure of the compounds and the magnitude of their biological activity was determined.
Experimental studies in vitro have identified substances with antibacterial, antifungal, antioxidant and antitumor activity among the synthesized compounds of a number of triazenes and hydrazones of 9,10-anthracendione.
