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Directed synthesis and chemical transformations of new nitrogen- and oxygen-containing heterocyclic compounds for bioanalytical and pharmacological purposes


Work number - M 38 FILED

Presented State Higher Educational Institution “Ukrainian State University of Chemical Technology”

Authors:
Dr.S. Farat O.K., Ph.D. Varenichenko S.A., Ph.D. Kulyk O.G., Ph.D. Sanin E.V.

 

The authors have been developed the effective methods for the synthesis of a number of new nitrogen- and oxygen-containing heterocyclic compounds, studied their transformations in reactions of alkylation, acylation, deacylation, heterocyclization, carbo[3+3]cyclocondensation, Dimroth rearrangement, Claisen-Schmidt and Knoevenagel condensations,  Michael and Vilsmeier-Haack reactions.

Five new electrophilic rearrangements of oxazaheterocyclic systems upon the conditions of Vilsmeier-Haack reaction were discovered and the necessary criteria for their performance were disclosed. Previously unknown o-hydroxyphenyl derivatives of 2‑(1'H,2H-3,4'-dipyrazol-5-yl)phenol(naphthol) and 2,2'-diamino-4,5'-bipyrimidin-6-yl-phenol(naphthol) were synthesized. The fundamental difference between the reactivity of 4H-chromen-4-imines and derivatives of 4H-chromon-4-ones in the reaction with malonodinitrile was shown. A systematic study of low molecular weight 4-alkyl-3,4‑dihydropyrimidin-2(1H)-one derivatives and related compounds was carried out for the first time.

The relationships between the electronic structure and spectral properties of new derivatives of xanthene dyes, cinnamoyl-α-pyrones, coumaroylbenzopyrylium salts and squaraines were investigated.

Based on the results of in silico prediction and biochemical in vitro and in vivo testing of the obtained compounds, a number of bioactive samples demonstrating antifungal, antibacterial, antitumor and neurotropic activity were revealed. 

The obtained results were implemented in the educational process of the department of pharmacy and technology of organic substances of USUCT according to the corresponding document. Besides, a number of fluorescent dyes obtained during the present work, are regularly supplied on a commercial basis to the American company SETA BioMedicals LLC, where they are used for biochemical and bioanalytical investigations, which is confirmed by the appropriate certificate.

Number of publications: 64 articles in scientific domestic and foreign journals (where 45 publications are referred in the Scopus database) and 93 abstracts of conference reports. The total number of citations to publications of authors/Hirsch index of the presented work, according to the databases, is respectively: Web of Science - 108/6, Scopus - 147/7, Google Scholar - 235/9.

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