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Synthesis of nucleoside 5 '-O-alpha,beta-methylene-beta-triphosphates and evaluation of their potency towards inhibition of HIV-1 reverse transcriptase

  1. Author:
    Ahmadibeni, Y.
    Dash, C.
    Hanley, M. J.
    Le Grice, S. F. J.
    Agarwal, H. K.
    Parang, K.

  2. Author Address

    [Ahmadibeni, Y.; Hanley, M. J.; Agarwal, H. K.; Parang, K.] Univ Rhode Isl, Coll Pharm, Dept Biomed & Pharmaceut Sci, Kingston, RI 02881 USA. [Dash, C.] Meharry Med Coll, Ctr AIDS Hlth Dispar Res, Nashville, TN 37208 USA. [Ahmadibeni, Y.] Columbus State Univ, Dept Chem, Columbus, GA 31907 USA. [Le Grice, S. F. J.] NCI, Resistance Mech Lab, HIV Drug Resistance Program, Natl Inst Hlth, Frederick, MD 21702 USA.;Parang, K, Univ Rhode Isl, Coll Pharm, Dept Biomed & Pharmaceut Sci, Kingston, RI 02881 USA.;kparang@uri.edu
    1. Year: 2010
    2. Date: Mar
  2. Journal: Organic & Biomolecular Chemistry
    1. 8
    2. 6
    3. Pages: 1271-1274
  4. Type of Article: Article
  5. ISSN: 1477-0520
  1. Abstract:

    A polymer-bound alpha,beta-methylene-beta-triphosphitylating reagent was synthesized and subjected to reactions with unprotected nucleosides, followed by oxidation, deprotection of cyanoethoxy groups, and acidic cleavage to afford nucleoside 5 '-O-alpha,beta-methylene-beta-triphosphates. Among all the compounds, cytidine 5 '-O-alpha,beta-methylene-beta-triphosphate inhibited RNase H activity of HIV-1 reverse transcriptase with a K-i value of 225 mu M.

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External Sources

  1. View Full Text
  2. DOI: 10.1039/b922846b
  3. View record in Web of Science®
  4. WOS: 000275187000003

Library Notes

  1. Fiscal Year: FY2009-2010
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