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


  • 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



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


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.