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Solid-phase synthesis of 5 '-O-beta,gamma-methylenetriphosphate derivatives of nucleosides and evaluation of their inhibitory activity against HIV-1 reverse transcriptase

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

  2. Author Address

    [Ahmadibeni, Yousef; Parang, Keykavous] Univ Rhode Isl, Coll Pharm, Dept Biomed & Pharmaceut Sci, Kingston, RI 02881 USA. [Ahmadibeni, Yousef] Columbus State Univ, Dept Chem, Columbus, GA 31907 USA. [Dash, Chandravanu] Meharry Med Coll, Ctr AIDS Hlth Dispar Res, Nashville, TN 37208 USA. [Le Grice, Stuart F. J.] NCI, Resistance Mech Lab, HIV Drug Resistance Program, NIH, Frederick, MD 21702 USA.;Parang, K, Univ Rhode Isl, Coll Pharm, Dept Biomed & Pharmaceut Sci, Kingston, RI 02881 USA.;kparang@gmail.com
    1. Year: 2010
    2. Date: Jun
  2. Journal: Tetrahedron Letters
    1. 51
    2. 22
    3. Pages: 3010-3013
  4. Type of Article: Article
  5. ISSN: 0040-4039
  1. Abstract:

    Bis(dichlorophosphino)methane was converted to a beta,gamma-methylenetriphosphitylating reagent. The reagent was immobilized on aminomethyl polystyrene resin-bound linker of 4-acetoxy-3-phenylbenzyl alcohol to afford a polymer-bound beta,gamma-methylenetriphosphitylating reagent, which was reacted with unprotected nucleosides followed by oxidation with tert-butyl hydroperoxide, deprotection of cyanoethoxy groups with DBU, and acidic cleavage to produce 5'-O-beta,gamma-methylene triphosphate nucleosides in 53- 82% overall yields. Among all the compounds, cytidine 5'-O-beta,gamma-methylenetriphosphate inhibited completely RNase H activity of HIV-1 reverse transcriptase at 700 mu M. (C) 2010 Elsevier Ltd. All rights reserved.

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External Sources

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  2. DOI: 10.1016/j.tetlet.2010.04.005
  3. View record in Web of Science®
  4. WOS: 000278128500018

Library Notes

  1. Fiscal Year: FY2009-2010
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