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Green synthesis of new sulfanyl derivatives of ampyrone and prediction of their anti-inflammatory activity

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Chemistry of Heterocyclic Compounds Aims and scope

A selective method was developed for the synthesis of acyclic sulfanyl derivatives of ampyrone by thiomethylation reaction of 4-amino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one with formaldehyde and thiols in aqueous medium under various conditions (room temperature, 80°C, ultrasonication or microwave irradiation). A series of the synthesized sulfanyl derivatives of ampyrone were characterized with regard to their anti-inflammatory activity by molecular docking method using the AutoDock 4.2 and AutoDock Vina software. The steric complementarity with the active sites of cyclooxygenase isoforms (COX-1 and COX-2) was explored.

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This work received financial support from the Russian Science Foundation (project 19-73-00070).

The results were obtained with the financial support of the Ministry of Science and Higher Education of the Russian Federation (grant 2019-05-595-000-058) using the equipment of the Regional Collective Use Center “Agidel” (Ufa Federal Research Center, Russian Academy of Sciences).

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Authors and Affiliations

  1. Russian Academy of Sciences, Institute of Petrochemistry and Catalysis, 141 Oktyabrya Ave, Ufa, 450075, Russia

    Nail S. Akhmadiev, Ekaterina S. Mescheryakova, Vnira R. Akhmetova & Askhat G. Ibragimov

  2. Bashkir State University, 32 Zaki Validi St, Ufa, 450076, Russia

    Veronika R. Khairullina

Authors
  1. Nail S. Akhmadiev
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  2. Ekaterina S. Mescheryakova
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  3. Veronika R. Khairullina
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  4. Vnira R. Akhmetova
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  5. Askhat G. Ibragimov
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Correspondence to Vnira R. Akhmetova.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(4), 473–481

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Akhmadiev, N.S., Mescheryakova, E.S., Khairullina, V.R. et al. Green synthesis of new sulfanyl derivatives of ampyrone and prediction of their anti-inflammatory activity. Chem Heterocycl Comp 56, 473–481 (2020). https://doi.org/10.1007/s10593-020-02683-8

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