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Synthesis and evaluation of antiviral activity of 2′-deoxyuridines with 5-methylene-2-thiohydantoin substituents in the 5-position

Synthese und Testung der antiviralen Aktivität von 2′-Deoxyuridinen mit 5-Methylen-2-thiohydantoin-Substituenden in der 5-Position

  • Organische Chemie Und Biochemie
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Summary

1-(2-Deoxy-3,5-bis-O-(4-methylbenzoyl)-D-erythro-pentofuranosyl)-5-formyluracil (4) was synthesized from 5-formyluracil and an appropriate methyl glycoside and condensed with 2-thiohydantoin (5a) and its corresponding 3-phenyl derivative5b to give 5-[1-(2-deoxy-3,5-bis-O-(4-methylbenzoyl)-D-erythro-pentofuranosyl)uracil-5-ylmethylene]-2-thiohydantoins7a and7b, respectively, in 65–70% yield. They were deprotected with sodium methoxide in methanol to give both anomers of the free nucleosides. In a different route 5-formyluracil (1) was condensed with5b and subsequently with an appropriate methyl glycoside to give7b.

Zusammenfassung

1-(2-Deoxy-3,5-bis-O-(4-methylbenzoyl)-D-erythro-pentofuranosyl)-5-formyluracil (4) wurde aus 5-Formylurazil und dem entsprechenden Methylglycosid synthetisiert und mit 2-Thiohydantoin (5a) und seinem 3-Phenylderivat5b kondensiert, wobei die 5-[1-(2-Deoxy-3,5-bis-O-(4-methylbenzoyl)-D-erythro-pentofuranosyl)uracil-5-ylmethylene]-2-thiohydantoine7a bzw.7b in 65–70% Ausbeute erhalten wurden. Nach Entfernung der Schutzgruppen mit Natriummethoxid in Methanol erhielt man beide Anomeren der freien Nucleoside. Auf einem anderen Weg wurde 5-Formyluracil (1) mit5b und anschließend mit einem entsprechenden Methylglycosid zu7b kondensiert.

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Authors and Affiliations

  1. Department of Chemistry, Odense University, DK-5230, Odense M, Denmark

    A. A. El-Barbary, A. I. Khodair & E. B. Pedersen

  2. Retrovirus Laboratory, Enterovirus Department, Statens Seruminstitut, DK-2300, Copenhagen, Denmark

    C. Nielsen

Authors
  1. A. A. El-Barbary
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  2. A. I. Khodair
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  3. E. B. Pedersen
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  4. C. Nielsen
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On leave from Chemistry Department, Faculties of Science and Education, Tanta University, Tanta, Egypt

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El-Barbary, A.A., Khodair, A.I., Pedersen, E.B. et al. Synthesis and evaluation of antiviral activity of 2′-deoxyuridines with 5-methylene-2-thiohydantoin substituents in the 5-position. Monatsh Chem 125, 593–598 (1994). https://doi.org/10.1007/BF00811853

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  • DOI: https://doi.org/10.1007/BF00811853

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