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Allenols Derived from Nucleic Acid Bases — A New Class of Anti-HIV Agents: Chemistry and Biological Activity

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Nucleosides and Nucleotides as Antitumor and Antiviral Agents

Abstract

The last 15 years have witnessed a revival of interest in analogues of nucleosides following the discoveries that several of such compounds exhibit powerful antiviral effects. In this context, two compounds are of particular significance. The first of such analogues is acyclovir (1a, Zovirax) which was developed in the late seventies1 (Chart 1). Acyclovir (1a) is an analogue of 2′-deoxyguanosine of clinical importance as a drug for treatment of herpesvirus infections. The second compound is 3′-azido-3′-deoxythymidine (3b, AZT, zidovudine or Retrovir), an analogue of thymidine, and, until recently, the only approved drug for treatment of acquired immunodeficiency syndrome (AIDS). AZT (3b) was originally prepared in the sixties,2 its antiretroviral potential was recognized in the seventies,3 and it was developed as a therapeutic agent against AIDS in the eighties.4 Drugs 1a and 3b are examples of two structurally different classes of nucleoside analogues. Acyclovir (1a) belongs to a series of open-chain compounds derived by cleavage of at least one C-C bond or deletion of one or more carbon atoms of the sugar ring, whereas AZT (3b) comprises an intact furanose moiety.

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  1. Department of Chemistry, Michigan Cancer Foundation and Departments of Internal Medicine and Biochemistry, Wayne State University School of Medicine, Detroit, Michigan, 48201, USA

    Jiri Zemlicka

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  1. The University of Georgia, Athens, Georgia

    Chung K. Chu

  2. The University of Tennessee, Knoxville, Tennessee, USA

    David C. Baker

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Zemlicka, J. (1993). Allenols Derived from Nucleic Acid Bases — A New Class of Anti-HIV Agents: Chemistry and Biological Activity. In: Chu, C.K., Baker, D.C. (eds) Nucleosides and Nucleotides as Antitumor and Antiviral Agents. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-2824-1_4

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