Title: Synthesis and Biological Activity of 3-Aryl-5-(aryloxymethyl)-1,2,4-oxadiazoles.
Authors: Shetnev, A. A.; Vasilieva, E. A.; Proskurina, I. K.; Forostyanko, A. S.; Presnukhina, S. I.; Tarasenko, M. V.; Lebedev, A. S.; Ivanovskii, S. A.; Kotov, A. D.
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.
Subjects: BIOSYNTHESIS; CHEMICAL synthesis; PSEUDOMONAS fluorescens; GUT microbiota; BACILLUS subtilis
Publication: Russian Journal of Organic Chemistry, 2022, Vol 58, Issue 3, p306
ISSN: 1070-4280
Publication type: Academic Journal
DOI: 10.1134/S1070428022030071

Synthesis and Biological Activity of 3-Aryl-5-(aryloxymethyl)-1,2,4-oxadiazoles.

Shetnev, A. A.; Vasilieva, E. A.; Proskurina, I. K.; Forostyanko, A. S.; Presnukhina, S. I.; Tarasenko, M. V.; Lebedev, A. S.; Ivanovskii, S. A.; Kotov, A. D.