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Synthesis of 2-[(ω-phthalimidoalkyl)sulfanyl]- pyrimidin-4(3H)-ones, their cytotoxicity and in vitro activity against HIV-1/2

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Chemistry of Heterocyclic Compounds Aims and scope

The interaction of N-(2-bromoethyl)- and N-(3-bromopropyl)phthalimides with 2-thiouracils substituted at position 6 was studied in alkaline medium, providing S-monoamidoalkylation products and, depending on the substituents, the products of S,O(4)- and S,N(3)-diamidoalkylation. Among the obtained compounds, only 2-[2-(phthalimidoethyl)sulfanyl]-6-(trifluoromethyl)pyrimidin- 4(3H)-one showed in vitro antiHIV-1 and antiHIV-2 activity at micromolar concentration range.

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This study received financial support from the Russian Science Foundation (grant 19-13-00123) and was performed on the equipment of IOC-Acrus Ltd.

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Authors and Affiliations

  1. Volgograd State Technical University, 28 Lenina Ave., Volgograd, 400005, Russia

    Ivan A. Novakov, Dmitry S. Sheikin, Viktor V. Chapurkin, Maksim B. Nawrozkij & Alexande S. Babushkin

  2. Volzhsky Polytechnic Institute (branch of the Volgograd State Technical University), 42a Engelsa St., Volzhsky, 404121, Russia

    Yaroslav P. Kuznetsov

  3. Closed Joint Stock Company Farm-Sintez, 2-46 2-ya Kabelnaya St., Moscow, 111024, Russia

    Evsey A. Ruchko

  4. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow, 119991, Russia

    Vadim V. Kachala

  5. LUKOIL-Volgogradneftepererabotka Ltd., 55 40 let VLKSM St., Volgograd, 400029, Russia

    Anton Yu. Maryshev

  6. Rega Institute for Medical Research, 10 Minderbroedersstraat, B1030 3000, Leuven, Belgium

    Dominique Schols

Authors
  1. Ivan A. Novakov
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  2. Dmitry S. Sheikin
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  3. Viktor V. Chapurkin
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  4. Maksim B. Nawrozkij
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  6. Yaroslav P. Kuznetsov
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  7. Evsey A. Ruchko
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  8. Vadim V. Kachala
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Corresponding author

Correspondence to Dmitry S. Sheikin.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(1), 67–72

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Novakov, I.A., Sheikin, D.S., Chapurkin, V.V. et al. Synthesis of 2-[(ω-phthalimidoalkyl)sulfanyl]- pyrimidin-4(3H)-ones, their cytotoxicity and in vitro activity against HIV-1/2. Chem Heterocycl Comp 56, 67–72 (2020). https://doi.org/10.1007/s10593-020-02624-5

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  • DOI: https://doi.org/10.1007/s10593-020-02624-5

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