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      Fluorine-Containing Diazines in Medicinal Chemistry and Agrochemistry

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          Abstract

          The combination of a fluorine atom and a diazine ring, which both possess unique structural and chemical features, can generate new relevant building blocks for the discovery of efficient fluorinated biologically active agents. Herein we give a comprehensive review on the biological activity and synthesis of fluorine containing, pyrimidine, pyrazine and pyridazine derivatives with relevance to medicinal and agrochemistry.

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          Fluorine in medicinal chemistry.

          Sophie Purser, Peter R. Moore, Steve Swallow … (2008)
          It has become evident that fluorinated compounds have a remarkable record in medicinal chemistry and will play a continuing role in providing lead compounds for therapeutic applications. This tutorial review provides a sampling of renowned fluorinated drugs and their mode of action with a discussion clarifying the role and impact of fluorine substitution on drug potency.
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            Mechanism of action of T-705 against influenza virus.

            Yousuke Furuta, Kazumi Takahashi, Masako Kuno-Maekawa … (2005)
            T-705, a substituted pyrazine compound, has been found to exhibit potent anti-influenza virus activity in vitro and in vivo. In a time-of-addition study, it was indicated that T-705 targeted an early to middle stage of the viral replication cycle but had no effect on the adsorption or release stage. The anti-influenza virus activity of T-705 was attenuated by addition of purines and purine nucleosides, including adenosine, guanosine, inosine, and hypoxanthine, whereas pyrimidines did not affect its activity. T-705-4-ribofuranosyl-5'-triphosphate (T-705RTP) and T-705-4-ribofuranosyl-5'-monophosphate (T-705RMP) were detected in MDCK cells treated with T-705. T-705RTP inhibited influenza virus RNA polymerase activity in a dose-dependent and a GTP-competitive manner. Unlike ribavirin, T-705 did not have an influence on cellular DNA or RNA synthesis. Inhibition of cellular IMP dehydrogenase by T-705RMP was about 150-fold weaker than that by ribavirin monophosphate, indicating the specificity of the anti-influenza virus activity and lower level of cytotoxicity of T-705. These results suggest that T-705RTP, which is generated in infected cells, may function as a specific inhibitor of influenza virus RNA polymerase and contributes to the selective anti-influenza virus activity of T-705.
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              Fluorinated pyrimidines, a new class of tumour-inhibitory compounds.

              CHARLES HEIDELBERGER, N. K. Chaudhuri, PETER DANNEBERG … (1957)
              Article 0 comments Cited 190 times – based on 0 reviews     Review now
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                Author and article information

                Contributors
                Valentine Nenajdenko: nenajdenko@gmail.com
                Dmitriy M. Volochnyuk: d.volochnyuk@gmail.com
                Journal
                Journal ID (publisher-id): 978-3-319-04435-4
                Journal ID (doi): 10.1007/978-3-319-04435-4
                Journal ID (nlm-ta): Fluorine in Heterocyclic Chemistry Volume 2
                Title: Fluorine in Heterocyclic Chemistry Volume 2
                Subtitle: 6-Membered Heterocycles
                ISBN (Print): 978-3-319-04434-7
                ISBN (Electronic): 978-3-319-04435-4
                Publication date (Electronic): 13 June 2014
                Pages: 577-672
                Affiliations
                GRID grid.14476.30, ISNI 0000000123429668, Department of Chemistry, , Moscow State University, ; Moscow, Russia
                [2 ]GRID grid.464621.3, ISNI 0000000404974742, Biologically Active Compound Department, , Institute of Organic Chemistry, National Academy of Sciences of Ukraine, ; Murmanska Street 5, Kyiv, 02660 Ukraine
                [3 ]GRID grid.34555.32, ISNI 0000000403858248, Department of Chemistry, , National Taras Shevchenko University of Kyiv, ; Volodymyrska Street, 64, Kyiv, 01601 Ukraine
                Article
                Publisher ID: 7
                DOI: 10.1007/978-3-319-04435-4_7
                PMC ID: 7121506
                SO-VID: 6999925d-4b06-4d07-9176-d56cfa062242
                Copyright © © Springer International Publishing Switzerland 2014
                License:

                This article is made available via the PMC Open Access Subset for unrestricted research re-use and secondary analysis in any form or by any means with acknowledgement of the original source. These permissions are granted for the duration of the World Health Organization (WHO) declaration of COVID-19 as a global pandemic.

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                Subject: Article
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                issue-copyright-statement © Springer International Publishing Switzerland 2014

                Keywords: pyrimidine,pyrazine,pyridazine,fluorine,bioactive compounds,medicinal chemistry,agrochemistry
                Data availability:
                Keywords: pyrimidine, pyrazine, pyridazine, fluorine, bioactive compounds, medicinal chemistry, agrochemistry

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