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3-(2-Arylhydrazono)-1,1,1-trifluro-3-(phenylsulfonyl)propan-2-ones as selective carboxylesterase inhibitors

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Abstract

We improved the synthetic procedure for 3-(2-arylhydrazono)-1,1,1-trifluro-3-(phenylsulfonyl)propan-2-ones and established their structure. The study of their esterase profile showed the absence of cholinesterase inhibition and the selectivity against carboxylesterase with micromolar activity exceeding the anticarboxylesterase activity of the diketone analog. Carboxylesterase inhibition data are consistent with molecular docking results. 3-(2-Arylhydrazono)-1,1,1-trifluro-3-(phenylsulfonyl)propan-2-ones exhibit a high radical-scavenging effect in the ABTS test exceeding that of Trolox.

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Authors and Affiliations

  1. I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 ul. S. Kovalevskoi/Akademicheskaya, 620108, Ekaterinburg, Russian Federation

    E. V. Shchegolkov, Ya. V. Burgart, N. A. Elkina, A. N. Perminova & V. I. Saloutin

  2. Institute of Physiologically Active Compounds, Russian Academy of Sciences, 1 Severny proezd, 142432, Chernogolovka, Moscow Region, Russian Federation

    N. P. Boltneva, O. G. Serebryakova, E. V. Rudakova & G. F. Makhaeva

  3. N. M. Emanuel Institute of Biochemical Physics, Russian Academy of Sciences, 4 ul. Kosygina, 119991, Moscow, Russian Federation

    S. V. Lushchekina

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  1. E. V. Shchegolkov
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Correspondence to V. I. Saloutin.

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Dedicated to Academician of the Russian Academy of Sciences O. M. Nefedov on the occasion of his 90th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 158–164, January, 2022.

The work was carried out using the equipment of the Centre for Joint Use “Spectroscopy and Analysis of Organic Compounds” (CJU “SAOC”). Molecular modeling was performed using the equipment of the Centre for Shared Use of the Ultra-High Performance Computing Resources of the M. V. Lomonosov Moscow State University.

This work was financially supported by the Russian Foundation for Basic Research (Project No. 20-03-00312) and by the Russian state assignment to the Institute of Physiologically Active Compounds of the Russian Academy of Sciences (No. 0090-2019-0005, biochemical studies).

No human or animal subjects were used in this research.

The authors declare no competing interests.

The work was carried out using the equipment of the Centre for Joint Use “Spectroscopy and Analysis of Organic Compounds” (CJU “SAOC”). Molecular modeling was performed using the equipment of the Centre for Shared use of the Ultra-High Performance Computing Resources of the M. V. Lomonosov Moscow State University.

This work was fi nancially supported by the Russian Foundation for Basic Research (Project No. 20-03-00312) and by the Russian state assignment to the Institute of Physiologically Active Compounds of the Russian Academy of Sciences (No. 0090-2019-0005, biochemical studies).

No human or animal subjects were used in this research.

The authors declare no competing interests.

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Shchegolkov, E.V., Boltneva, N.P., Burgart, Y.V. et al. 3-(2-Arylhydrazono)-1,1,1-trifluro-3-(phenylsulfonyl)propan-2-ones as selective carboxylesterase inhibitors. Russ Chem Bull 71, 158–164 (2022). https://doi.org/10.1007/s11172-022-3390-9

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