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Synthesis and Biological Activity of 8-(Dialkylamino)-3-aryl-6-oxo-2,4-dicyanobicyclo[3.2.1]octane-2,4-dicarboxylic Acids Diethyl Esters

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Abstract

Cascade reaction of 2 equiv. of furfural (or equimolar amounts of furfural and aromatic aldehyde) with secondary amines and ethyl cyanoacetate afforded diethyl esters of 8-(dialkylamino)-3-aryl-6-oxo-2,4-dicyanobicyclo[3.2.1]octane-2,4-dicarboxylic acids with yields of 37–54%. Antimicrobial activity of a number of obtained compounds in vitro was studied, and biological activity in silico was analyzed. The obtained bicyclo[3.2.1]octanes are inactive or exhibit weak fungicidal activity, but exhibit moderate bactericidal effect.

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Funding

This work was financially supported by the Ministry of Education and Science of the Russian Federation (project no. 0795-2020-0031).

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Authors and Affiliations

  1. Baku State University, AZ1148, Baku, Azerbaijan

    A. I. Ismiyev, M. Shoaib, K. G. Ganbarov, A. A. Israilova & A. M. Magerramov

  2. Kuban State University, 350040, Krasnodar, Russia

    V. V. Dotsenko

  3. North Caucasus University, 355009, Stavropol, Russia

    V. V. Dotsenko

Authors
  1. A. I. Ismiyev
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  2. M. Shoaib
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  3. V. V. Dotsenko
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  6. A. M. Magerramov
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Correspondence to A. I. Ismiyev.

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Ismiyev, A.I., Shoaib, M., Dotsenko, V.V. et al. Synthesis and Biological Activity of 8-(Dialkylamino)-3-aryl-6-oxo-2,4-dicyanobicyclo[3.2.1]octane-2,4-dicarboxylic Acids Diethyl Esters. Russ J Gen Chem 90, 1418–1425 (2020). https://doi.org/10.1134/S1070363220080071

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  • DOI: https://doi.org/10.1134/S1070363220080071

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