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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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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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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 (2020). https://doi.org/10.1007/s10593-020-02624-5

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Keywords

  • 2-thiouracil
  • uracil
  • phthalimidoalkylation
  • antiHIV-1/2 activity
  • antiviral activity