Azomethines based on ethyl 4-formyl-3,5-dimethyl-1H-pyrrole-2-carboxylate, its biological activity and reaction with thioglycolic acid
Olena I. Mikhedkina
1
,
Valeriia V. Ananieva
1
,
Yana I Sakhno
2
,
Igor I. Melnyk
1
,
Vladyslav O. Vereshchak
1
,
Tetiana P. Osolodchenko
3
,
Svitlana V. Shishkina
2, 4
,
Alexander V. Tsygankov
1, 2
,
Valentyn A Chebanov
2, 4
1
National Technical University “Kharkiv Polytechnic Institute”, Kharkiv, Ukraine
|
2
Division of Functional Materials Chemistry, State Scientific Institution “Institute for Single Crystals”, NationalAcademyofSciencesofUkraine, Kharkiv, Ukraine
|
3
Mechnikov Institute of Microbiology and Immunology, National Academy of Medical Sciences of Ukraine, Kharkiv, Ukraine
|
4
Faculty of Chemistry, V. N. Karazin Kharkiv National University, Kharkiv, Ukraine
|
Publication type: Journal Article
Publication date: 2023-07-01
scimago Q4
wos Q4
SJR: 0.243
CiteScore: 2.7
Impact factor: 1.0
ISSN: 00093122, 15738353
Organic Chemistry
Abstract
Condensation of ethyl 4-formyl-3,5-dimethyl-1H-pyrrole-2-carboxylate with various aromatic amines and with 5-amino-3-(4-bromo- phenyl(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.
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Mikhedkina O. I. et al. Azomethines based on ethyl 4-formyl-3,5-dimethyl-1H-pyrrole-2-carboxylate, its biological activity and reaction with thioglycolic acid // Chemistry of Heterocyclic Compounds. 2023. Vol. 59. No. 6-7. pp. 449-455.
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Mikhedkina O. I., Ananieva V. V., Sakhno Y. I., Melnyk I. I., Vereshchak V. O., Osolodchenko T. P., Shishkina S. V., Tsygankov A. V., Chebanov V. A. Azomethines based on ethyl 4-formyl-3,5-dimethyl-1H-pyrrole-2-carboxylate, its biological activity and reaction with thioglycolic acid // Chemistry of Heterocyclic Compounds. 2023. Vol. 59. No. 6-7. pp. 449-455.
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TY - JOUR
DO - 10.1007/s10593-023-03215-w
UR - https://doi.org/10.1007/s10593-023-03215-w
TI - Azomethines based on ethyl 4-formyl-3,5-dimethyl-1H-pyrrole-2-carboxylate, its biological activity and reaction with thioglycolic acid
T2 - Chemistry of Heterocyclic Compounds
AU - Mikhedkina, Olena I.
AU - Ananieva, Valeriia V.
AU - Sakhno, Yana I
AU - Melnyk, Igor I.
AU - Vereshchak, Vladyslav O.
AU - Osolodchenko, Tetiana P.
AU - Shishkina, Svitlana V.
AU - Tsygankov, Alexander V.
AU - Chebanov, Valentyn A
PY - 2023
DA - 2023/07/01
PB - Springer Nature
SP - 449-455
IS - 6-7
VL - 59
SN - 0009-3122
SN - 1573-8353
ER -
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@article{2023_Mikhedkina,
author = {Olena I. Mikhedkina and Valeriia V. Ananieva and Yana I Sakhno and Igor I. Melnyk and Vladyslav O. Vereshchak and Tetiana P. Osolodchenko and Svitlana V. Shishkina and Alexander V. Tsygankov and Valentyn A Chebanov},
title = {Azomethines based on ethyl 4-formyl-3,5-dimethyl-1H-pyrrole-2-carboxylate, its biological activity and reaction with thioglycolic acid},
journal = {Chemistry of Heterocyclic Compounds},
year = {2023},
volume = {59},
publisher = {Springer Nature},
month = {jul},
url = {https://doi.org/10.1007/s10593-023-03215-w},
number = {6-7},
pages = {449--455},
doi = {10.1007/s10593-023-03215-w}
}
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MLA
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Mikhedkina, Olena I., et al. “Azomethines based on ethyl 4-formyl-3,5-dimethyl-1H-pyrrole-2-carboxylate, its biological activity and reaction with thioglycolic acid.” Chemistry of Heterocyclic Compounds, vol. 59, no. 6-7, Jul. 2023, pp. 449-455. https://doi.org/10.1007/s10593-023-03215-w.