SYNTHESIS OF NITROGEN-CONTAINING HETEROCYCLIC COMPOUNDS BASED ON 9,10-ANTHRAQUINONE DERIVATIVES

A simple glance at FDA databases reveals the structural significance of nitrogen-based heterocycles in the drug design and engineering of pharmaceuticals, with nearly 60 % of unique small-molecule drugs containing a nitrogen heterocycle. Many heterocyclic scaffolds can be considered as privilege structures. According to statistics, more than 85 % of all biologically-active chemical entities contain a heterocycle. The application of anthraquinone heterocycles provides a useful tool for modification of solubility, lipophilicity, polarity, and hydrogen bonding capacity of biologically active agents, which results in the optimization of the ADME/Tox properties of drugs or drug candidates. The review is devoted to the synthesis of heterocyclic compounds, derivatives of anthraquinone, obtained by reactions of nucleophilic substitution, diazotization, cycloaddition, isomerization and rearrangement, published over the past 20 years. Aminoanthraquinones and their diazo derivatives were most often used as starting materials for the production of nitrogen-containing heterocycles based on anthraquinone. The collected material shows that the the structure dynamics involved in anthraquinone nitrogen-based heterocycles, alongside with fundamental aspects such as ring size and aromaticity, translates into a vast array of chemical structures by which their molecular mechanisms of action can vary significantly.