Open Access
Synthesis, Antibacterial and Antifungal Activity of New 3-Aryl-5H-pyrrolo[1,2-a]imidazole and 5H-Imidazo[1,2-a]azepine Quaternary Salts
Sergii Demchenko
1
,
Roman Lesyk
2
,
Oleh Yadlovskyi
1
,
Johannes Zuegg
3
,
Iryna Drapak
4
,
Yuliia Fedchenkova
5
,
Zinaida Suvorova
1
,
Anatolii Demchenko
1, 5
1
Institute of Pharmacology and Toxicology, Antona Tsedika 14, 03057 Kyiv, Ukraine
|
4
Department of General, Inorganic, Physical and Colloidal Chemistry, Danylo Halytsky Lviv National Medical University, Pekarska 69, 79010 Lviv, Ukraine
|
5
Department of Chemistry and Pharmacy, Nizhyn Mykola Gogol State University, 16600 Nizhyn, Ukraine
|
Publication type: Journal Article
Publication date: 2021-07-13
PubMed ID:
34299528
Organic Chemistry
Drug Discovery
Physical and Theoretical Chemistry
Pharmaceutical Science
Molecular Medicine
Analytical Chemistry
Chemistry (miscellaneous)
Abstract
A series of novel 3-aryl-5H-pyrrolo[1,2-a]imidazole and 5H-imidazo[1,2-a]azepine quaternary salts were synthesized in 58–85% yields via the reaction of 3-aryl-6, 7-dihydro-5H-pyrrolo[1,2-a]imidazoles or 3-aryl-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepines and various alkylating reagents. All compounds were characterized by 1H NMR, 13C NMR, and LC-MS. The conducted screening studies of the in vitro antimicrobial activity of the new quaternary salts derivatives established that 15 of the 18 newly synthesized compounds show antibacterial and antifungal activity. Synthesized 3-(3,4-dichlorohenyl)-1-[(4-phenoxyphenylcarbamoyl)-methyl]-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-1-ium chloride 6c possessed a broad activity spectrum towards Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae, Acinetobacter baumannii, and Cryptococcus neoformans, with a high hemolytic activity against human red blood cells and cytotoxicity against HEK-293. However, compound 6c is characterized by a low in vivo toxicity in mice (LD50 > 2000 mg/kg).
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17
Total citations:
17
Citations from 2025:
2
(11.76%)
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GOST
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Demchenko S. et al. Synthesis, Antibacterial and Antifungal Activity of New 3-Aryl-5H-pyrrolo[1,2-a]imidazole and 5H-Imidazo[1,2-a]azepine Quaternary Salts // Molecules. 2021. Vol. 26. No. 14. p. 4253.
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Demchenko S., Lesyk R., Yadlovskyi O., Zuegg J., Elliott A. G., Drapak I., Fedchenkova Y., Suvorova Z., Demchenko A. Synthesis, Antibacterial and Antifungal Activity of New 3-Aryl-5H-pyrrolo[1,2-a]imidazole and 5H-Imidazo[1,2-a]azepine Quaternary Salts // Molecules. 2021. Vol. 26. No. 14. p. 4253.
Cite this
RIS
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TY - JOUR
DO - 10.3390/molecules26144253
UR - https://doi.org/10.3390/molecules26144253
TI - Synthesis, Antibacterial and Antifungal Activity of New 3-Aryl-5H-pyrrolo[1,2-a]imidazole and 5H-Imidazo[1,2-a]azepine Quaternary Salts
T2 - Molecules
AU - Demchenko, Sergii
AU - Lesyk, Roman
AU - Yadlovskyi, Oleh
AU - Zuegg, Johannes
AU - Elliott, Alysha G.
AU - Drapak, Iryna
AU - Fedchenkova, Yuliia
AU - Suvorova, Zinaida
AU - Demchenko, Anatolii
PY - 2021
DA - 2021/07/13
PB - MDPI
SP - 4253
IS - 14
VL - 26
PMID - 34299528
SN - 1420-3049
ER -
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BibTex (up to 50 authors)
Copy
@article{2021_Demchenko,
author = {Sergii Demchenko and Roman Lesyk and Oleh Yadlovskyi and Johannes Zuegg and Alysha G. Elliott and Iryna Drapak and Yuliia Fedchenkova and Zinaida Suvorova and Anatolii Demchenko},
title = {Synthesis, Antibacterial and Antifungal Activity of New 3-Aryl-5H-pyrrolo[1,2-a]imidazole and 5H-Imidazo[1,2-a]azepine Quaternary Salts},
journal = {Molecules},
year = {2021},
volume = {26},
publisher = {MDPI},
month = {jul},
url = {https://doi.org/10.3390/molecules26144253},
number = {14},
pages = {4253},
doi = {10.3390/molecules26144253}
}
Cite this
MLA
Copy
Demchenko, Sergii, et al. “Synthesis, Antibacterial and Antifungal Activity of New 3-Aryl-5H-pyrrolo[1,2-a]imidazole and 5H-Imidazo[1,2-a]azepine Quaternary Salts.” Molecules, vol. 26, no. 14, Jul. 2021, p. 4253. https://doi.org/10.3390/molecules26144253.