AZOMETHINES BASED ON ETHYL 4-FORMYL-3,5-DIMETHYL-1<i>H</i>-PYRROLE-2-CARBOXYLATE, ITS BIOLOGICAL ACTIVITY AND REACTION WITH THIOGLYCOLIC ACID

Authors

  • Olena I. Mikhedkina National Technical University ''Kharkiv Polytechnic Institute'', 2 Kyrpychova St., Kharkiv 61002, Ukraine
  • Valeriia V. Ananieva National Technical University ''Kharkiv Polytechnic Institute'', 2 Kyrpychova St., Kharkiv 61002, Ukraine
  • Yana I. Sakhno Division of Functional Materials Chemistry, State Scientific Institution “Institute for Single Crystals” of NAS of Ukraine
  • Igor I. Melnyk National Technical University ''Kharkiv Polytechnic Institute'', 2 Kyrpychova St., Kharkiv 61002, Ukraine
  • Vladyslav O. Vereshchak National Technical University ''Kharkiv Polytechnic Institute'', 2 Kyrpychova St., Kharkiv 61002, Ukraine
  • Tetiana P. Osolodchenko Mechnikov Institute of Microbiology and Immunology, National Academy of Medical Sciences of Ukraine, 14 Pushkinska St., Kharkiv 61057, Ukraine
  • Svitlana V. Shishkina Division of Functional Materials Chemistry, State Scientific Institution ''Institute for Single Crystals'', National Academy of Sciences of Ukraine, 60 Nauky Ave., Kharkiv 61072, Ukraine
  • Alexander V. Tsygankov National Technical University ''Kharkiv Polytechnic Institute'', 2 Kyrpychova St., Kharkiv 61002, Ukraine Division of Functional Materials Chemistry, State Scientific Institution ''Institute for Single Crystals'', National Academy of Sciences of Ukraine, 60 Nauky Ave., Kharkiv 61072, Ukraine
  • Valentyn A. Chebanov Division of Functional Materials Chemistry, State Scientific Institution ''Institute for Single Crystals'', National Academy of Sciences of Ukraine, 60 Nauky Ave., Kharkiv 61072, Ukraine Faculty of Chemistry, V. N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv 61022, Ukraine

DOI:

https://doi.org/10.1007/7128

Keywords:

5-aminopyrazole, azomethine, 4-formyl-3, 5-dimethyl-1H-pyrrole-2-carboxylate, pyrrole derivative, biological activity.

Abstract

Condensation of ethyl 4-formyl-3,5-dimethyl-1H-pyrrole-2-carboxylate with various aromatic amines and with 5-amino-3-(4-bromophenyl(tolyl))-1H-pyrazole in absolute boiling ethanol afforded new azomethines as Schiff bases. The structure and E-configuration of the azomethine fragment were detected by the methods of 1H NMR spectroscopy and X-ray analysis. Reaction of these compounds with thioglycolic acid in toluene, DMF, or AcOH at reflux with or without the addition of ZnCl2 as well as under microwave irradiation had an unusual pathway leading to the formation of ethyl 3,5-dimethyl-4-(5-oxo-1,3-oxathiolan-2-yl)-1H-pyrrole-2-carboxylate exclusively. The obtained azomethines were found to be effective only against Gram positive bacteria, whereas ethyl 4-{(E)-[(4-chlorophenyl)imino]methyl}-3,5-dimethyl-1H-pyrrole-2-carboxylate exhibited the highest antibacterial activity.

Author Biographies

Olena I. Mikhedkina, National Technical University ''Kharkiv Polytechnic Institute'', 2 Kyrpychova St., Kharkiv 61002, Ukraine

Associate Professor, Candidate of Chemical Sciences.

Valeriia V. Ananieva, National Technical University ''Kharkiv Polytechnic Institute'', 2 Kyrpychova St., Kharkiv 61002, Ukraine

Assistant professor, Candidate of Technical Sciences.

Yana I. Sakhno, Division of Functional Materials Chemistry, State Scientific Institution “Institute for Single Crystals” of NAS of Ukraine

Candidate of Chemical Sciences.
Senior researcher of the Laboratory of physical and chemical processes of the State Scientific Institution "Institute for Single Crystals"

Igor I. Melnyk, National Technical University ''Kharkiv Polytechnic Institute'', 2 Kyrpychova St., Kharkiv 61002, Ukraine

Associate professor of the Department of Organic Chemistry, Biochemistry, Paints and Coatings of the National Technical University “Kharkiv Polytechnic Institute”

Tetiana P. Osolodchenko, Mechnikov Institute of Microbiology and Immunology, National Academy of Medical Sciences of Ukraine, 14 Pushkinska St., Kharkiv 61057, Ukraine

Doctor of biological sciences, Ph.D.
Head of Laboratory of Biochemistry and Biotechnology of the Mechnikov Institute of Microbiology and Immunology of the NAMS of Ukraine.

Svitlana V. Shishkina, Division of Functional Materials Chemistry, State Scientific Institution ''Institute for Single Crystals'', National Academy of Sciences of Ukraine, 60 Nauky Ave., Kharkiv 61072, Ukraine

Candidate of Chemical Sciences.
Head of the Department of X-ray Diffraction Studies and Quantum Chemistry of the State Scientific Institution "Institute for Single Crystals".
ORCID ID: 0000-0002-3946-1061

Alexander V. Tsygankov, National Technical University ''Kharkiv Polytechnic Institute'', 2 Kyrpychova St., Kharkiv 61002, Ukraine Division of Functional Materials Chemistry, State Scientific Institution ''Institute for Single Crystals'', National Academy of Sciences of Ukraine, 60 Nauky Ave., Kharkiv 61072, Ukraine

Professor, Doctor of Chemical Sciences.
Head of the Department of Organic Chemistry, Biochemistry, Paints and Coatings of the National Technical University “Kharkiv Polytechnic Institute”.
Leading researcher of the Department of Organic and Bioorganic Chemistry of the State Scientific Institution "Institute for Single Crystals" .
ORCID ID: 0000-0001-5298-8450

Valentyn A. Chebanov, Division of Functional Materials Chemistry, State Scientific Institution ''Institute for Single Crystals'', National Academy of Sciences of Ukraine, 60 Nauky Ave., Kharkiv 61072, Ukraine Faculty of Chemistry, V. N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv 61022, Ukraine

Corresponding Memberof NAS of Ukraine (Microwave Organic Synthesis), Professor, DoctorofChemical Sciences.First Deputy General Director, Director of the Division of Functional Materials Chemistry, Head of the Laboratory for Physicochemical Processes of the State Scientist Institution "Institute for Single Crystals".
Head and Full Professor of the Department of Applied Chemistry of the Karazin Kharkiv National University.
ORCID ID: 0000-0001-7564-778X

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Published

2023-08-09

Issue

Vol. 59 No. 6/7 (2023): Ukrainian impact on heterocyclic chemistry after the three decades of independence

Section

Original Papers