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Synthesis and Antimonoamine Oxidase Activity of 2-(3-Iminoisoindol-1-ylidene)-2-arylacetonitriles

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Abstract

A one-pot synthesis of 2-(3-iminoisoindol-1-ylidene)-2-arylacetonitriles in yields of up to 95% by the cascade condensation of phthalonitrile with arylacetonitriles in a superbasic NaOH/DMSO medium was proposed. A method for the synthesis of (E)-2-(3-oxoisoindol-1-ylidene)-2-arylacetonitriles by the hydrolysis of 2-(3-iminoisoindol-1-ylidene)-2-arylacetonitriles in acetic acid was developed. The obtained (E)-2-(3-iminoisoindol-1-ylidene)-2-arylacetonitriles were shown to be active inhibitors of human monoamine oxidase [IC50(MAO-A) for (E)-2-(3-iminoisoindol-1-ylidene)-2-(4-methylphenyl)acetonitrile 3.26 µM].

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Funding

The work was supported financially by the Ministry of Education of the Russian Federation within the framework of the state order No. 073-00077-21-02 for scientific research on the topic “Development of an innovative drug for the treatment of open-angle glaucoma by selective inhibition of carbonic anhydrase II” (registry entry no. 730000F.99.1. BV10AA00006).

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Authors and Affiliations

  1. Ushinskii Yaroslavl State Pedagogical University, 150000, Yaroslavl, Russia

    A. I. Grigor’eva & A. D. Kotov

  2. Pharmaceutical Technology Transfer Center, Ushinskii Yaroslavl State Pedagogical University, 150000, Yaroslavl, Russia

    A. A. Shetnev & S. A. Ivanovskii

  3. Pharmaceutical Chemistry and Centre of Excellence for Pharmaceutical Sciences, North-West University, 2520, Potchefstroom, South Africa

    A. Petzer & J. P. Petzer

Authors
  1. A. I. Grigor’eva
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  2. A. A. Shetnev
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  3. A. D. Kotov
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  4. S. A. Ivanovskii
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  5. A. Petzer
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  6. J. P. Petzer
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Corresponding author

Correspondence to A. D. Kotov.

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Additional information

Translated from Zhurnal Organicheskoi Khimii, 2022, Vol. 58, No. 5, pp. 476–483 https://doi.org/10.31857/S0514749222050044.

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Grigor’eva, A.I., Shetnev, A.A., Kotov, A.D. et al. Synthesis and Antimonoamine Oxidase Activity of 2-(3-Iminoisoindol-1-ylidene)-2-arylacetonitriles. Russ J Org Chem 58, 663–668 (2022). https://doi.org/10.1134/S1070428022050049

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  • DOI: https://doi.org/10.1134/S1070428022050049

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