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

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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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Funding

Studies in the field of synthesis of the target compounds were performed under financial support by the Russian Foundation for Basic Research (project no. 19-33-600-64). Biological activity of the synthesized compounds was studied under financial support by the Ministry of Education of the Russian Federation (project no. 073-00077-21-02, “Development of an Innovative Drug for the Treatment of Open-Angle Glaucoma via Selective Inhibition of Carbonic Anhydrase II”; state registry no. 730000F.99.1.BV10AA00006).

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Authors and Affiliations

  1. Dorogov Pharmaceutical Technology Transfer Center, Ushinsky Yaroslavl State Pedagogical University, 150000, Yaroslavl, Russia

    A. A. Shetnev, S. I. Presnukhina, M. V. Tarasenko & S. A. Ivanovskii

  2. Ushinsky Yaroslavl State Pedagogical University, 150000, Yaroslavl, Russia

    E. A. Vasilieva, I. K. Proskurina, A. S. Forostyanko & A. D. Kotov

  3. Demidov Yaroslavl State University, 150003, Yaroslavl, Russia

    A. S. Lebedev

Authors
  1. A. A. Shetnev
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  2. E. A. Vasilieva
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  3. I. K. Proskurina
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  4. A. S. Forostyanko
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  5. S. I. Presnukhina
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  6. M. V. Tarasenko
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  7. A. S. Lebedev
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  8. S. A. Ivanovskii
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  9. A. D. Kotov
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Correspondence to A. A. Shetnev.

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Additional information

Translated from Zhurnal Organicheskoi Khimii, 2022, Vol. 58, No. 3, pp. 293–302 https://doi.org/10.31857/S0514749222030077.

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Shetnev, A.A., Vasilieva, E.A., Proskurina, I.K. et al. Synthesis and Biological Activity of 3-Aryl-5-(aryloxymethyl)-1,2,4-oxadiazoles. Russ J Org Chem 58, 306–314 (2022). https://doi.org/10.1134/S1070428022030071

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  • DOI: https://doi.org/10.1134/S1070428022030071

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