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Synthesis and properties of new derivatives of 4-amino-2,3-polymethylenequinolines with antioxidant function

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Abstract

New potential multitarget compounds based on 4-amino-2,3-polymethylenequinolines (analogs of tacrine) with different sizes of aliphatic rings conjugated with an ionol molecule as an antioxidant moiety were synthesized. The addition was accomplished through the ethyleneamine linker using an amide bond. The study of the esterase profile of the synthesized compounds showed that they are highly efficient inhibitors of both acetylcholinesterase and butyrylcholinesterase with high selectivity for the latter and exhibit high antioxidant activity in the ABTS test (ABTS is the 2,2–-azinobis(3-ethylbenzothiazoline-6-sulfonic acid)).

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Authors and Affiliations

  1. Institute of Physiologically Active Compounds, Federal Research Center for Problems of Chemical Physics and Medicinal Chemistry of the Russian Academy of Sciences, 1 Severnyiproezd, 142432, Chernogolovka, Moscow Region, Russian Federation

    I. V. Serkov, A. N. Proshin, N. V. Kovaleva, N. P. Boltneva, E. V. Rudakova, G. F. Makhaeva & S. O. Bachurin

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  1. I. V. Serkov
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  2. A. N. Proshin
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  3. N. V. Kovaleva
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  4. N. P. Boltneva
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  5. E. V. Rudakova
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  6. G. F. Makhaeva
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  7. S. O. Bachurin
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Corresponding author

Correspondence to I. V. Serkov.

Additional information

Dedicated to Academician of the Russian Academy of Sciences I. P. Beletskaya on the occasion of her anniversary.

The study was carried out within the framework of the Russian State Assignment of the Institute of Physiologically Active Compounds of the Russian Academy of Sciences (IPAC RAS) FFSN-2021-0005, part of the work was financially supported by the Russian Foundation for Basic Research (Project No. 20-03-00590-a). The equipment of the Center for Collective Use of the IPAC RAS was used in the work (Agreement No. 14.621.21.0008, work identifier RFMEFI62114X0008).

No human or animal subjects were used in this research.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 3, pp. 802–806, March, 2023.

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Serkov, I.V., Proshin, A.N., Kovaleva, N.V. et al. Synthesis and properties of new derivatives of 4-amino-2,3-polymethylenequinolines with antioxidant function. Russ Chem Bull 72, 802–806 (2023). https://doi.org/10.1007/s11172-023-3844-8

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  • DOI: https://doi.org/10.1007/s11172-023-3844-8

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