Methods of synthesis, structure and biological activity of 5-nitro-9-N-arylaminoacridines

Authors

  • S. G. Isaev National University of Pharmacy, Ukraine
  • H. O. Yeryomina National University of Pharmacy, Ukraine
  • T. A. Kostina National University of Pharmacy, Ukraine
  • N. Yu. Sheveleva National University of Pharmacy, Ukraine

DOI:

https://doi.org/10.24959/ophcj.14.805

Keywords:

synthesis, 5-nitro-9-N-arylaminoacridines, pharmacological activity

Abstract

With the purpose of search of new biologically active substances the synthesis of nine derivatives of 5-nitro-9-Narylaminoacridinium (2a-i) has been carried out by interaction of the corresponding 5-nitro-9-chloracridines and aromatic amines in two ways: in the phenol medium (method A) and in the dioxane medium in the presence of hydrochloric acid (method B). It has been experimentally proven that method B is more expedient because it is characterized by the absence of toxic phenol in the synthesis, reduction of the experiment time, a high yield of the desired product (87-94%). The structure and individuality of compounds synthesized that are undescribed in the literature have been confirmed by IR-, NMR-spectral and chromatographic analysis. The choice of the pharmacological screening spectrum has been conducted using data of PASS-prognosis, scientific and patent literature. It has been found experimentally that the substances synthesized possess a moderate bacteriostatic and fungistatic, expressed anti-inflammatory and analgesic, high diuretic (compounds 2d-f) and antidiuretic (compounds 2h-i) activities. According to the classification by K.K.Sydorov the compounds synthesized when introduced intragastrically belong to low toxic compounds. Some regularities of the “structure – biological activity – toxicity” dependence have been analyzed, and it is an important element in determining the areas for further research to develop new biologically active substances.

Downloads

Download data is not yet available.

References

  1. Volyanskiy Yu. L., Krestetska S. L. Visn. nauk. doslidzhen – Journal of scientific research, 2002, No.4, pp.5-8. 1. Ershov F. I., Kiselev V. I., Kiselev O. I. Vestnik Rossiyskoy Akademii med. nauk – Bulletin of the Russian Academy of med. sciences, 2004, No.2, pp.29-34.
  2. Gregory D. Cuny, Maxime Robin, Natalia P. Ulyanova, Debasis Patnaik, Valerie Pique, Gilles Casano, Ji-Feng Liu, Xiangjie Lin, Jun Xian, Marcie A. Glicksman, Ross L. Stein, Jonathan M. G. Higgins. Bioorg. & Med. Chem. Letters, 2010, Vol. 20, Is. 12. pp.3491-4394.
  3. Malachowska-Ugartea M., Cholewinskia G., Dzierzbickaa K., Trzonkowskib P. Eur. J. Med. Chem., 2012, Vol. 54, No.8, pp.197-201.
  4. Tlegenov R. T. Him.-farmats. zhurn. – Chem.-pharm. Journal, 2008, Vol. 42, No.10, pp.27-28.
  5. Stefanov O. V. Doklinichni doslidzhennya likarskih zasobiv: metod. rekomendatsiyi (Preclinical studies of drugs: methodical recommendations). Kiyiv: Avitsenna, 2001, 528 p.

Published

2014-09-12

How to Cite

(1)
Isaev, S. G.; Yeryomina, H. O.; Kostina, T. A.; Sheveleva, N. Y. Methods of Synthesis, Structure and Biological Activity of 5-Nitro-9-N-Arylaminoacridines. J. Org. Pharm. Chem. 2014, 12, 49-53.

Issue

Section

Original Researches