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Synthesis of substances with high antitumor activity against tumors with high drug resistance

Name of the project

Synthesis of substances with high antitumor activity against tumors with high drug resistance based on indolyl aryl acetamides and related substances

Head of the project and main contributors:

Head of the project: Aksenov Nikolai Aleksandrovich – Doctor of Chemistry, associate professor of the Chair of Chemistry, the Institute of Mathematics and Natural Sciences

Project realization support mechanisms:

The project was supported by the results of the 2019 competition for grants from the Russian Science Foundation for the event “Initiative Research by Young Scientists” of the Presidential Programme of research projects implemented by leading scientists, including young scientists (project number: 19-73-00091)

University subdivisions and industrial partners involved in the project:

Chair of Chemistry, the Institute of Mathematics and Natural Sciences

Project description

Project realization is aimed at solving the fundamental problem of finding new reagents for organic synthesis and creation of new synthetic methods, as well as discovering compounds with high biological activity among the synthesized substances, and creation of new materials for microelectronics.

As part of the project, a new method is being sought to obtain congeners of aryl (indol-3-yl) acetamides, as these compounds are interesting for their anticancer activity. This is determined, first of all, by the previously discovered activity of structurally similar indolylacetohydroxamic acids. Development of a library of such substances will make it possible to identify the leading compounds and establish the relationship between structure and biological activity. During the project, first of all, the synthesis of the starting compounds will be carried out. 4-Oxo-2,4-diarylbutyronitriles were obtained from the corresponding chalcones, a method for the synthesis of (E) -2- (3-oxoindolin-2-ylidene) -2-phenylacetonitriles by the interaction of 2'-nitrochalcones with KCN was developed. Much attention during the second stage of the project will be focused on highly efficient cascade transformations, which will create a number of original synthetic methods and obtain compounds with valuable applied properties. Within the framework of the project, the Fisher reaction between 4-oxo-2,4-diarylbutyronitriles and arylhydrazines in the medium of polyphosphoric acid was also investigated, and a series of 2- (indol-2-yl) acetamides were synthesized, which are of the greatest interest for the purposes of studying activity with respect to various cancer cell cultures, including those in enantiomerically pure form. It was revealed that derivatives containing 3,4-dimethylphenyl, β-naphthyl or 5,6,7,8-tetrahydronaphthalen-2-yl substituents are the most active ones. In collaboration with colleagues from New Mexico Tech and Texas State University, the obtained compounds were tested for anti-cancer cytostatic activity using HeLa cervical cancer cells and MCF-7 breast cancer cultures.

Current project results

A completely original method was found for the preparation of (E) -2- (3-oxoindolin-2-ylidene) -2-phenylacetonitriles - substances similar in structure to natural purpura and many drugs, which suggests possible profits from studying the properties of these compounds. A method for stereoselective preparation of indolylacetamides has been developed. Biological tests of the obtained substances for anticancer cytostatic activity were carried out, including tests in the form of individual enantiomers. A number of compounds with an activity of less than 1µM in relation to HeLa and MCF 7 cultures were detected.

During the implementation of the project, 1 article was published, indexed by Web of Science and Scopus. The results of the study were accepted for publication in the RSC advances journal.

  1. Unexpected Cyclization of ortho-Nitrochalcones into 2-Alkylideneindolin-3-ones RSC Advances (2020). Aksenov N.A., Aksenov D.A., Arutiunov N.A., Aksenova D.S., Aksenov A.V., Rubin M.

Expected results

At least 2 articles indexed in Web of science and Scopus will be published based on the results of the work during the second year of the project. The results of scientific research are planned to be presented in the framework of 2 international conferences.

Prospects for practical use

Successful implementation of the project will provide a library of new biologically active compounds with high antitumor activity in relation to tumors with high drug resistance based on indolyl aryl acetamides and related compounds.