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Synthesis and conformational analysis of a locked analogue of carbovir built on a bicyclo 3.1.0 hex-2-enyl template

  1. Author:
    Choi, Y. S.
    Sun, G. Y.
    George, C.
    Nicklaus, M. C.
    Kelley, J. A.
    Marquez, V. E.

  2. Author Address

    NCI, Frederick Canc Res & Dev Ctr, Ctr Canc Res, Med Chem LabNHI, Frederick, MD 21702 USA NCI, Frederick Canc Res & Dev Ctr, Ctr Canc Res, Med Chem LabNHI, Frederick, MD 21702 USA USN, Res Lab, Struct Matter Lab, Washington, DC 20375 USA Marquez VE NCI, Frederick Canc Res & Dev Ctr, Ctr Canc Res, Med Chem LabNHI, Frederick, MD 21702 USA
    1. Year: 2003
  2. Journal: Nucleosides Nucleotides & Nucleic Acids
    1. 22
    2. 12
    3. Pages: 2077-2091
  4. Type of Article: Article
  1. Abstract:

    The synthesis and biological evaluation of a carbovir analogue (5) built on a bicyclo[3.1.0]hex-2-enyl template is described. A conformational analysis using density functional theory at the B3LYP/6-31G* level has been carried out on the rigid pseudosugar template of 5, the cyclopentene moiety of carbovir and the bicyclo[3.1.0]hex-2-yl pseudosugars of two isomeric carbonucleosides (12 and 13) containing exo- and endo-fused cyclopropane rings. The results show that while the planar configuration of the fused cyclopentane ring of compound 5 helps retain weak anti-HIV activity, the ability of the cyclopentene ring of carbovir to easily adopt a planar or puckered conformation with little energy penalty may prove to be a crucial advantage. The bicyclo[3.1.0]hex-2-yl nucleosides 12 and 13 that were inactive against HIV exhibited stiffer resistance to having a planar, fused cyclopentane moiety.

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