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The Synthesis and Reactions of Pyrrole, Pyrazole, Triazole, Indole, Indazole, and Benzotriazole Nucleosides and Nucleotides

  • Chapter
Chemistry of Nucleosides and Nucleotides

Abstract

The nucleosides and nucleotides of pyrrole, pyrazole, triazole, and the corresponding benzoderivatives have been prepared as analogues of purine nucleosides, purine nucleotides, or their biological precursors. The size and geometry of azole nucleosides are similar to the biologically important imidazole nucleosides, while the indole, indazole, and benzotriazole derivatives are closer to those of the corresponding purine derivatives. However, the properties of these compounds, such as electronic density distribution in the heterocyclic moiety, the value and direction of dipole moments, ability to accommodate intermolecular interactions, and, finally, the reactivity of substituents (including the lability of the glycosidic bond) in these compounds, are very different. Indole, indazole, and benzotriazole nucleosides are unique analogues of purine nucleosides, since there are no nitrogen atoms in the “pyrimidine” ring.

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Authors and Affiliations

  1. Institute of New Antibiotics, Russian Academy of Medical Sciences, Moscow, 119867, Russia

    Maria N. Preobrazhenskaya

  2. Cancer Research Center, Russian Academy of Medical Sciences, Moscow, 115478, Russia

    Ilya A. Korbukh

  3. Beckman Instruments, 2500 Harbor Boulevard, Fullerton, California, 92634, USA

    Ilya A. Korbukh

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  1. Maria N. Preobrazhenskaya
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  1. University of Michigan, Ann Arbor, Michigan, USA

    Leroy B. Townsend

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Preobrazhenskaya, M.N., Korbukh, I.A. (1994). The Synthesis and Reactions of Pyrrole, Pyrazole, Triazole, Indole, Indazole, and Benzotriazole Nucleosides and Nucleotides. In: Townsend, L.B. (eds) Chemistry of Nucleosides and Nucleotides. Springer, Boston, MA. https://doi.org/10.1007/978-1-4757-9667-4_1

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