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

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

S. G. Isaev, H. O. Yeryomina, T. A. Kostina, N. Yu. Sheveleva

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.


Keywords


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

References


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.

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.

Malachowska-Ugartea M., Cholewinskia G., Dzierzbickaa K., Trzonkowskib P. Eur. J. Med. Chem., 2012, Vol. 54, No.8, pp.197-201.

Tlegenov R. T. Him.-farmats. zhurn. – Chem.-pharm. Journal, 2008, Vol. 42, No.10, pp.27-28.

Stefanov O. V. Doklinichni doslidzhennya likarskih zasobiv: metod. rekomendatsiyi (Preclinical studies of drugs: methodical recommendations). Kiyiv: Avitsenna, 2001, 528 p.


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Abbreviated key title: Ž. org. farm. hìm.

ISSN 2518-1548 (Online), ISSN 2308-8303 (Print)