INTERACTION BETWEEN STRUCTURE AND ACTIVITY OF SYNTHESIZE TRIAZENES AT 4-SUBSTITUTED 9,10-ANTHRAQUINONE

2018;
136-145
1
Vasyl Stefanyk Precarpathian National University
2
Vasyl Stefanyk Precarpathian National University
3
Lviv Polytechnic National University
4
Lviv Polytechnic National University
5
Lviv Polytechnic National University

The article by authors Shupeniuk V.I., Taras T.M., Bolibruch L.D., Zhurahivska L.R., Gubitska I.I. “Іnteraction between structure and activity of synthesize triazenes at 4-substituted 9,10-anthraquinone" is devoted to the study of new triazenes that can be used as potentially biologically active compounds that have anti-tumor activity with anti-neoplastic action. In the article, the authors cover problems arising during the diazotization of 4-substituted derivatives 1-amino-9,10-dioxo-9,10-dyhidroanthracene-2-sulfanate, 1-amino-4-[(2-hydroxyethyl)amino]anthracene-9,10-dione and bromaminic acid depending on the position of the 4-substitute group in the aromatic ring. The authors present convenient methods of diazotization of 4-substituted 9,10-anthraquinone, which were developed based on the analysis of literature’s sources and own experimental data. With synthesized diazo-compounds, the authors of the article carried out the reaction of N-azocoupling with aliphatic, aromatic and hetero aromatic amines in maximum yield.

The article by authors Shupenyuk V.I., Taras T.M., Bolibruch L.D., Zhurahivska L.R., Gubitska I.I. consists of four parts. In the first part, the authors substantiate the purpose of the described research, show the need for the synthesis of new nitrogen-containing derivatives 9,10-anthraquinone. The second part of the article contains a thorough analysis of the previous studies of the diazotization reaction of 4-substituted 9,10-anthraquinone, and N-azocoupling for the synthesis of triazenes based on this analysis, substantiates the relevance of the described research. In the third part, the authors direct their research, give the irdiscussion and analysis. The authors of the article point out the data of the computer prediction of biological activity of the program PASS Online, аnd analyzed the influence of substituents in silico in synthesized 4-substituted triasenes on antitumor activity, show the need for the synthesis of triazenes with less toxic and carcinogenic effects. And also give the methods of diazotization, bromaminic acid diazotiated with nitrosyl sulfate acid in a concentrated sulfate acid medium. For the diazotization of 4-substituted derivatives of 9,10-anthraquinone, the nucleophilic substitution of bromine in bromaminic acid was proposed by a diazotization with aqueous sodium nitrite solution in the chloride acids was proposed. The proposed diazotization techniques allow the N-azocoupling reaction with aliphatic, aromatic and heterocyclic aromatic amines to be obtained with the maximum yield in order to obtain triazenes. The formation of the desired triazenes is confirmed by chromatо-mass-spectrometry data and NMR H1 spectroscopy, which is presented in the experimental part, together with the synthesis methods. The article concludes with the conclusions and list of used literary sources.

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