Abstract
This review is focused on the synthetic strategies to heterocyclic C-nucleosides and covers the literature from 2011 to 2021. The main attention is paid to the following three approaches: the direct C—C coupling of a carbohydrate moiety with a preformed aglycon unit, the construction of a (pseudo)sugar residue on a pre-formed aglycon, and the construction of an aglycon on a pre-formed (pseudo)sugar. In each Section, the literature data are categorized in terms of the size of aglycon from simple to complex, the advantages and drawbacks of the reviewed approaches are discussed.
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Rusinov Vladimir Leonidovich, born in 1947, Head of the Department of Organic and Biomolecular Chemistry, Head of the Laboratory of Organic Synthesis at the Scientific and Educational Innovation Center for Chemical and Pharmaceutical Technologies at the Ural Federal University named after the first President of Russia B. N. Yeltsin (UrFU), Corresponding Member of the Russian Academy of Sciences (RAS), Honored Chemist of the Russian Federation, laureate of the Prize of the Council of Ministers of the USSR, laureate of the N. D. Zelinsky Prize of the RAS, laureate of the International Prize Prix Galien Russia. V. L. Rusinov is a recognized specialist in the field of organic, heterocyclic and medicinal chemistry. He is the author of 437 scientific and educational articles (including 7 monographs and book chapters, 22 reviews, and 401 article in Russian and foreign journals), 107 inventor’s certificates and patents. V. L. Rusinov made a significant contribution to the concept of nucleophilic substitution of hydrogen. He discovered new reactions and carried out mechanistic studies on nucleophilic substitution of hydrogen in azine salts and azine N-oxides. Using 13C and 15N isotopic labels, the mechanisms of transformation of azines in the presence of nucleophiles were studied. He developed synthetic procedures and studied properties of a wide range of (nitroaza)purines, bearing one or more heterocyclic nitrogen atoms and an exocyclic nitro group. He participated in the development of a new class of antiviral drugs. The first representative of this series, Triazavirin, was produced on an industrial scale since 2014 and its effectiveness for the treatment and prevention of influ enza, SARS, tick-borne encephalitis, and COVID-19 was confirmed. A new class of antidiabetic compounds was found; the antiglycating drug AB-19 is being introduced into practice for the prevention and treatment of the complications of type 2 diabetes mellitus. V. L. Rusinov is a supervisor of the master’s program “Pharmaceutical Production Management” at UrFU. Under supervision of V. L. Rusinov, 19 PhD theses and two Doctor of Chemical Sciences (Habilitation) theses were devoted.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 2, pp. 425–481, February, 2023.
No human or animal subjects were used in this research.
The authors declare no competing interests.
This work was financially supported by the Russian Science Foundation (Project No. 22-23-00282).
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Mukhin, E.M., Savateev, K.V. & Rusinov, V.L. Approaches to the synthesis of heterocyclic C-nucleosides. Russ Chem Bull 72, 425–481 (2023). https://doi.org/10.1007/s11172-023-3810-1
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DOI: https://doi.org/10.1007/s11172-023-3810-1