Synthesis, computational and antimicrobial studies of new 1,4-naphthoquinone aminothiazole derivatives

Authors

  • I. Buchkevych Lviv Polytechnic National University
  • M. Stasevych Lviv Polytechnic National University
  • V. Chervetsova Lviv Polytechnic National University
  • R. Musyanovych Lviv Polytechnic National University
  • V. Novikov Lviv Polytechnic National University
  • V. Poroikov Orekhovich Institute of Biomedical Chemistry of the Russian Academy of Medical Sciences
  • T. Gloriozova Orekhovich Institute of Biomedical Chemistry of the Russian Academy of Medical Sciences
  • D. Filimonov Orekhovich Institute of Biomedical Chemistry of the Russian Academy of Medical Sciences
  • G. Zagoriy PJSC Pharmaceutical Company “Darnitsa”
  • M. Ponomarenko P. L. Shupik National Medical Academy of Post-Graduate Education

DOI:

https://doi.org/10.5755/j01.ct.61.3.2847

Keywords:

naphthoquinone, thiocyanate, thiourea, thiazole, heterocyclization, biological activities, computational prediction, computer program PASS, antimicrobial action

Abstract

Synthesis of new aminothiazole derivatives on the basis of substituted 1,4-naphthoquinones was carried out by interaction of 2-R-3,6-dichloro-7-acylamino-1,4-naphthoquinones and potassium thiocyanate, 3,6-dichloro-2,7-diacylamino-1,4-naphthoquinone and dithiocyanate, interaction of 2-R-3,6-dichloro-7-amino-1,4-naphthoquinones, 2-amino-7-nitro-3,6-dichloro-1,4-naphthoquinone and thiourea with the subsequent cyclization in aminothiazoles of 1,4-naphthoquinone. Physical and chemical properties of these compounds were determined, and the methods of their preparation are presented. Computer program PASS was used for prediction of biological activity spectra of new 1,4-naphthoquinone aminothiazole derivatives, to determine the most promising biological activities for experimental testing. Antibacterial and fungicidal activities were studied using cultures of Staphylococcus aureus, Escherichia coli and Candida tenuis microorganisms. It was found that some of the studied compounds have moderate antibacterial and fungicide activity, which in more than 90 % cases coincided with the computational predictions. Analysis of structure – antimicrobial activity relationships provides the recommendations for design of new derivatives. Some other biological activities have been predicted by PASS for these compounds, including antiviral, antineoplastic, immunomodulator, acute neurological disease treatment, antiparkinsonian, etc., which help to identify areas for further research. Thus, it was shown that 1,4-naphthoquinone aminothiazole derivatives is a promising class for preparation of novel pharmacological agents for different indications.

DOI: http://dx.doi.org/10.5755/j01.ct.61.3.2847

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Published

2012-11-13

Issue

Section

TECHNOLOGY OF ORGANIC MATERIALS