- An Unexpected Synthesis of a Dihydropyrrolo-[1,2-c]pyrimidinedione Nucleoside Analogue from 5-Fluorouracil
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In the presence of an excess of LDA, the tandem deprotonation-alkylation reaction of 1-cyanomethyl-5-fluorouracil with epibromohydrin gives the novel dihydropyrrolo[1,2-c]pyrimidinedione 4 as a mixture of diastereoisomers.
- Grangier-McMath, Geraldine,Aitken, David J.,Guillaume, Dominique,Chiaroni, Angele,Riche, Claude,Husson, Henri-Philippe
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- Synthesis of C-4′Truncated Phosphonated Carbocyclic 2′-Oxa-3′-azanucleosides as Antiviral Agents
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A new template of C-4′-truncated phosphonated nucleosides (TPCOANs) has been obtained in good yields according to two different routes which exploit the reactivity of a phosphonated nitrone. The one-step procedure based on the 1,3-dipolar cycloaddition of a phosphonated nitrone with vinyl nucleobases leads to the unnatural α-nucleosides as the main adducts. On the other hand, the target β-anomers have been obtained in high yield by a two-step procedure based on the 1,3-dipolar cycloaddition of a phosphonated nitrone with vinyl acetate followed by nucleosidation reaction. The reactivity of the phosphonated nitrone has been investigated trough quantum mechanical DFT calculations at the B3LYP/D95+(d,p) theory level. Preliminary biological assays show that β-anomers of TPCOANs are able to inhibit the reverse trancriptase of different retroviruses at concentrations in the nanomolar range, with a potency comparable with that of tenofovir.
- Piperno, Anna,Giofre, Salvatore V.,Iannazzo, Daniela,Romeo, Roberto,Romeo, Giovanni,Chiacchio, Ugo,Rescifina, Antonio,Piotrowska, Dorota G.
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experimental part
p. 2798 - 2805
(2010/07/17)
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- Uracil analogues of the acylonucleoside 9--methyl>guanine (BIOLF-62)
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A series of substituted uracil analogues of the antiviral agent 9-methyl>guanine (BIOL-62) has been synthesized and characterized.The uracil analogues show little activity against herpesviruses.
- Ogilvie, Kelvin K.,Hamilton, Raymond G.,Gillen, Michael F.,Radatus, Bruno K.,Smith, Kendall O.,Galloway, Karen S.
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- Novel uracil derivatives, process for preparing the same and a pharmaceutical composition containing the same
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Novel uracil derivatives of the formula STR1 (wherein R1, R2 R3 and X are defined in the description) and their pharmaceutically acceptable salts, process for preparing the same and pharmaceutical composition containing the same are disclosed. The uracil derivatives have good antitumor activity and, therefore, are useful as antitumor preparation.
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- Silylation of 5-fluoro-6-hydroxy or alkoxy pyrimidine
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A process for producing bis-silyl derivatives of fluorinated pyrimidines is disclosed, wherein a 5-fluoro-6-hydroxy or alkoxy pyrimidine is reacted with a silane, such as triethylchlorosilane. The intermediate product produced by that reaction, which is obtained in high yield, may then be reacted with a further compound, which can be a blocked sugar halide or 2-chlorotetrahydrofuran, to produce a nucleoside of the pyrimidine. The nucleosides are useful as antibacterial and antiviral agents, and in the treatment of cancer.
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