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

Authors

  • Vasyl I. Shupeniuk Precarpathian National University. V. Stefanyk, Ukraine
  • Tetyana N. Taras Precarpathian National University. V. Stefanyk, Ukraine
  • Oksana P. Sabadakh Precarpathian National University. V. Stefanyk, Ukraine
  • Evgeny R. Luchkevich Precarpathian National University. V. Stefanyk, Ukraine
  • Nikolay P. Matkivsky Precarpathian National University. V. Stefanyk, Ukraine

DOI:

https://doi.org/10.15421/082013

Keywords:

triazene, heterocyclization, nucleophilic substitution, condensation, cycloaddition, 9, 10-anthraquinones.

Abstract

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.

Author Biographies

Vasyl I. Shupeniuk, Precarpathian National University. V. Stefanyk

інженер кафедри хімії середовища та хімічної освіти

Tetyana N. Taras, Precarpathian National University. V. Stefanyk

завідувачка кафедри хімії середовища та хімічної освіти

Oksana P. Sabadakh, Precarpathian National University. V. Stefanyk

молодший науковий співробітник кафедри хімії середовища та хімічної освіти

Evgeny R. Luchkevich, Precarpathian National University. V. Stefanyk

старший науковий співробітник кафедри хімії середовища та хімічної освіти

Nikolay P. Matkivsky, Precarpathian National University. V. Stefanyk

старший науковий співробітник кафедри хімії середовища та хімічної освіти

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Published

2020-10-13

Issue

Vol. 28 No. 2 (2020): Journal of Chemistry and Technologies

Section

Organic Chemistry

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