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      Synthesis, reactivity and biological activity of 5-alkoxymethyluracil analogues

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          Summary

          This review article summarizes the results of a long-term investigation of 5-alkoxymethyluracil analogues and is aimed, in particular, at methods of syntheses. Most of the presented compounds were synthesized in order to evaluate their biological activity, therefore, a brief survey of biological activity, especially antiviral, cytotoxic and antibacterial, is also reported.

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          Fluorinated pyrimidines, a new class of tumour-inhibitory compounds.

          CHARLES HEIDELBERGER, N. K. Chaudhuri, PETER DANNEBERG … (1957)
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            (E)-5-(2-Bromovinyl)-2'-deoxyuridine: a potent and selective anti-herpes agent.

            F J Descamps, B. Galán, Stephanie Jones … (1979)
            Of a series of five newly synthesized 2'-deoxyuridine derivatives, including 5-vinyl-dUrd, 5-ethynyl-dUrd, 5-(1-chlorovinyl)-dUrd, (E)-5-(2-bromovinyl)-dUrd, and (E)-5-(2-iodovinyl)-dUrd, the last two compounds were found to exert a marked inhibitory effect on the replication of herpes simplex virus type 1 [ID50 (mean inhibitory dose), 0.004-0.02 microgram/ml]. Both (E)-5-(2-bromovinyl)-dUrd and (E)-5-(2-iodovinyl)-dUrd were highly selective in their anti-herpes activity in that they did not affect the growth or metabolism of the host (primary rabbit kidney) cells unless drug concentrations were used that were 5,000- to 10,000-fold greater than those required to inhibit virus multiplication. In this sense (E)-5-(2-bromovinyl)-dUrd and (E)-5-(2-iodovinyl)-dUrd proved more selective in their activity against herpes simplex virus type 1 than all other anti-herpes compounds that have been described so far. In animal model systems (namely, cutaneous herpes infections of athymic nude mice), (E)-5-(2-bromovinyl)-dUrd suppressed the development of herpetic skin lesions and mortality therewith associated, whether the compound was administered topically or systemically. Under the same conditions, the standard anti-herpes drug 5-iodo-dUrd (Idoxuridine) offered little, if any, protection. Although the precise mechanism of action of (E)-5-(2-bromovinyl)-dUrd and (E)-5-(2-iodovinyl)-dUrd remains to be established, preliminary findings indicate that they do not specifically act at the thymidylate synthetase step.
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              SYNTHESIS OF PSEUDOURIDINE

              Robert Shapiro, Robert Warner Chambers (1961)
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                Author and article information

                Contributors
                Jan Hlavac
                Jonathan Clayden: Role: Editor-in-Chief
                Journal
                Journal ID (nlm-ta): Beilstein J Org Chem
                Title: Beilstein Journal of Organic Chemistry
                Publisher: Beilstein-Institut (Trakehner Str. 7-9, 60487 Frankfurt am Main, Germany )
                ISSN (Electronic): 1860-5397
                Publication date Collection: 2011
                Publication date (Electronic): 26 May 2011
                Volume: 7
                Pages: 678-698
                Affiliations
                [1 ]Department of Organic Chemistry, Faculty of Science, Institute of Molecular and Translational Medicine, Palacky University, 17. Listopadu 12, 771 46 Olomouc, Czech Republic. Tel.: +420 585 634 405; Fax: +420 585 634 465
                Article
                DOI: 10.3762/bjoc.7.80
                PMC ID: 3135055
                PubMed ID: 21804865
                SO-VID: 79957bf3-7199-4a95-8ecf-61047d2efc3d
                Copyright © Copyright © 2011, Brulikova and Hlavac; licensee Beilstein-Institut.
                License:

                This is an Open Access article under the terms of the Creative Commons Attribution License ( http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

                The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: ( http://www.beilstein-journals.org/bjoc)

                History
                Date received : 15 February 2011
                Date accepted : 20 April 2011
                Categories
                Subject: Review
                Subject: Chemistry
                Subject: Organic Chemistry

                ScienceOpen disciplines: Organic & Biomolecular chemistry
                Keywords: 5-alkoxymethyluracil,biological activity,nucleosides
                Data availability:
                ScienceOpen disciplines: Organic & Biomolecular chemistry
                Keywords: 5-alkoxymethyluracil, biological activity, nucleosides

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