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Stereoselective Synthesis and Antiviral Activity of Novel 4′(α)-Hydroxymethyl and 6′(α)-Methyl Dually Branched Carbocyclic Nucleosides

  • 발행 : 2004.12.20

초록

The stereoselective synthesis 4′,6′-dually branched carbocyclic nucleosides was accomplished in this study. The introduction of a methyl group in the 6′$({\alpha})$-position was accomplished by Felkin-Anh controlled alkylation. The construction of the required 4′$({\alpha})$-quaternary carbon was carried out using a [3,3]-sigmatropic rearrangement. Bis-vinyl 6 was successfully cyclized using a Grubbs' catalyst II. The natural bases (adenine, cytosine) were efficiently coupled using a Pd(0) catalyst. When the synthesized compounds were examined for their activity against several viruses such as the HIV-1, HSV-1, HSV-2 and HCMV, the cytosine analogue 13 exhibited good antiviral activity against the HCMV.

키워드

참고문헌

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피인용 문헌

  1. Racemic Synthesis and Antiviral Evaluation of 4′(α)-Hydroxymethyl and 6′(α)-Methyl Substituted Apiosyl Nucleosides vol.26, pp.3, 2007, https://doi.org/10.1080/15257770701257491
  2. Stereoselective Synthesis and Antiviral Activity of Novel 4′(α)-Hydroxymethyl and 6′(α)-Methyl Dually Branched Carbocyclic Nucleosides. vol.36, pp.22, 2005, https://doi.org/10.1002/chin.200522202
  3. Synthesis and Antiviral Activity of Novel 4'-Branched Carbocyclic C-Nucleoside vol.26, pp.9, 2004, https://doi.org/10.5012/bkcs.2005.26.9.1366
  4. Chemoenzymatic synthesis of novel adenosine carbanucleoside analogues containing a locked 3′-methyl-2′,3′-β-oxirane-fused system vol.63, pp.23, 2007, https://doi.org/10.1016/j.tet.2007.03.122