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Synthesis and Anticholinesterase Activity of Some 2,5-Disubstituted Imidazol-4-ones Derived from the Green Fluorescent Protein Chromophore

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Abstract

2-Phenyl-4-[4-(benzoyloxy)benzylidene]-1,3-oxazol-5(4H)-ones reacted with hexamethyldisilazane to give, depending on the conditions, 3-aryl-2-benzamidoprop-2-enamides (ethyl acetate, 25°C) or 2-phenyl-5-(hydroxybenzylidene)-3,5-dihydro-4H-imidazol-4-ones (DMF, 150°C). The synthesized compounds were evaluated for their antiradical and anticholinesterase activities. O-Benzoyl derivatives were found to be inferior to compounds containing an α,β-didehydrotyrosine moiety with respect to antiradical activity, whereas imidazole derivatives generally showed a higher anticholinesterase activity than the corresponding α,β-dide­hydrotyrosine derivatives.

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Authors and Affiliations

  1. Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of Armenia, 0014, Yerevan, Armenia

    V. O. Topuzyan, A. A. Hovhannisyan & A. T. Makichyan

  2. Russian–Armenian University, 0051, Yerevan, Armenia

    A. T. Makichyan & L. S. Hunanyan

Authors
  1. V. O. Topuzyan
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  2. A. A. Hovhannisyan
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  3. A. T. Makichyan
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  4. L. S. Hunanyan
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Correspondence to A. T. Makichyan.

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Translated from Zhurnal Organicheskoi Khimii, 2022, Vol. 58, No. 7, pp. 706–717 https://doi.org/10.31857/S0514749222070035.

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Topuzyan, V.O., Hovhannisyan, A.A., Makichyan, A.T. et al. Synthesis and Anticholinesterase Activity of Some 2,5-Disubstituted Imidazol-4-ones Derived from the Green Fluorescent Protein Chromophore. Russ J Org Chem 58, 959–967 (2022). https://doi.org/10.1134/S107042802207003X

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