Synthesis and Biological Activity of 3-Aryl-5-(aryloxymethyl)-1,2,4-oxadiazoles
Anton A Shetnev
1
,
I K Proskurina
2
,
A S Forostyanko
2
,
Marina Tarasenko
1
,
A S Lebedev
3
,
S A Ivanovskii
1
,
Publication type: Journal Article
Publication date: 2022-03-01
scimago Q4
wos Q4
SJR: 0.190
CiteScore: 1.3
Impact factor: 0.9
ISSN: 10704280, 16083393
Organic Chemistry
Abstract
A preparative procedure has been developed for the synthesis of a series of new medicinally relevant 3-aryl-5-(aryloxymethyl)-1,2,4-oxadiazoles in 46–66% yields by alkylation of substituted phenols with 3-aryl-5-(chloromethyl)-1,2,4-oxadiazoles in the system K2CO3/KI/DMF. Poorly studied 3-R-4H-1,2,4-oxadiazin-5(6H)-ones were synthesized by a new method based on the reaction of methyl chloroacetate with amidoximes in the superbasic system t-BuONa/DMSO. The synthesized compounds at concentrations of up to 250 μg/mL showed no antibacterial activity against sensitive strains of Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Pseudomonas fluorescens, which supposedly suggests their low toxicity for human intestinal and mucous microflora.
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Shetnev A. A. et al. Synthesis and Biological Activity of 3-Aryl-5-(aryloxymethyl)-1,2,4-oxadiazoles // Russian Journal of Organic Chemistry. 2022. Vol. 58. No. 3. pp. 306-314.
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Shetnev A. A., Vasilieva E. A., Proskurina I. K., Forostyanko A. S., Presnukhina S. I., Tarasenko M., Lebedev A. S., Ivanovskii S. A., Kotov A. D. Synthesis and Biological Activity of 3-Aryl-5-(aryloxymethyl)-1,2,4-oxadiazoles // Russian Journal of Organic Chemistry. 2022. Vol. 58. No. 3. pp. 306-314.
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TY - JOUR
DO - 10.1134/S1070428022030071
UR - https://link.springer.com/10.1134/S1070428022030071
TI - Synthesis and Biological Activity of 3-Aryl-5-(aryloxymethyl)-1,2,4-oxadiazoles
T2 - Russian Journal of Organic Chemistry
AU - Shetnev, Anton A
AU - Vasilieva, Elmira A
AU - Proskurina, I K
AU - Forostyanko, A S
AU - Presnukhina, Sofia I
AU - Tarasenko, Marina
AU - Lebedev, A S
AU - Ivanovskii, S A
AU - Kotov, A D
PY - 2022
DA - 2022/03/01
PB - Pleiades Publishing
SP - 306-314
IS - 3
VL - 58
SN - 1070-4280
SN - 1608-3393
ER -
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@article{2022_Shetnev,
author = {Anton A Shetnev and Elmira A Vasilieva and I K Proskurina and A S Forostyanko and Sofia I Presnukhina and Marina Tarasenko and A S Lebedev and S A Ivanovskii and A D Kotov},
title = {Synthesis and Biological Activity of 3-Aryl-5-(aryloxymethyl)-1,2,4-oxadiazoles},
journal = {Russian Journal of Organic Chemistry},
year = {2022},
volume = {58},
publisher = {Pleiades Publishing},
month = {mar},
url = {https://link.springer.com/10.1134/S1070428022030071},
number = {3},
pages = {306--314},
doi = {10.1134/S1070428022030071}
}
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MLA
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Shetnev, Anton A., et al. “Synthesis and Biological Activity of 3-Aryl-5-(aryloxymethyl)-1,2,4-oxadiazoles.” Russian Journal of Organic Chemistry, vol. 58, no. 3, Mar. 2022, pp. 306-314. https://link.springer.com/10.1134/S1070428022030071.