Literature DB >> 20204192

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

Y Ahmadibeni1, C Dash, M J Hanley, S F J Le Grice, H K Agarwal, K Parang.   

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 microM.

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Year:  2010        PMID： 20204192      PMCID： PMC2928660          DOI： 10.1039/b922846b

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  32 in total

1.  A solid phase reagent for the capture phosphorylation of carbohydrates and nucleosides.

Authors:  K Parang; E J Fournier; O Hindsgaul
Journal:  Org Lett       Date:  2001-01-25       Impact factor: 6.005

2.  Differential inhibitory effects of several pyrimidine 2',3'-dideoxynucleoside 5'-triphosphates on the activities of reverse transcriptase and various cellular DNA polymerases.

Authors:  K Ono; H Nakane; P Herdewijn; J Balzarini; E De Clercq
Journal:  Mol Pharmacol       Date:  1989-05       Impact factor: 4.436

3.  (Difluoromethylene)phosphates of guanine nucleosides as probes of DNA polymerases and G proteins.

Authors:  L Arabshahi; N N Khan; M Butler; T Noonan; N C Brown; G E Wright
Journal:  Biochemistry       Date:  1990-07-24       Impact factor: 3.162

4.  Relationship between the inhibition constant (K1) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction.

Authors:  Y Cheng; W H Prusoff
Journal:  Biochem Pharmacol       Date:  1973-12-01       Impact factor: 5.858

5.  Inhibition of the RNase H activity of HIV reverse transcriptase by azidothymidylate.

Authors:  C K Tan; R Civil; A M Mian; A G So; K M Downey
Journal:  Biochemistry       Date:  1991-05-21       Impact factor: 3.162

6.  Using pyrrolo-deoxycytosine to probe RNA/DNA hybrids containing the human immunodeficiency virus type-1 3' polypurine tract.

Authors:  Chandravanu Dash; Jason W Rausch; Stuart F J Le Grice
Journal:  Nucleic Acids Res       Date:  2004-03-05       Impact factor: 16.971

7.  A novel method for the preparation of nucleoside triphosphates from activated nucleoside phosphoramidates.

Authors:  Weidong Wu; Caren L Freel Meyers; Richard F Borch
Journal:  Org Lett       Date:  2004-06-24       Impact factor: 6.005

Review 8.  New antiviral nucleoside prodrugs await application.

Authors:  Carole Anastasi; Gilles Quéléver; Stéphane Burlet; Cédrik Garino; Florence Souard; Jean-Louis Kraus
Journal:  Curr Med Chem       Date:  2003-09       Impact factor: 4.530

9.  Polymer-supported reagents for methylphosphorylation and phosphorylation of carbohydrates.

Authors:  Keykavous Parang
Journal:  Bioorg Med Chem Lett       Date:  2002-07-22       Impact factor: 2.823

10.  ATP analogues with modified phosphate chains and their selectivity for rat P2X2 and P2X2/3 receptors.

Authors:  Valeria Spelta; Abdelaziz Mekhalfia; Dominik Rejman; Mark Thompson; G Michael Blackburn; R Alan North
Journal:  Br J Pharmacol       Date:  2003-10-27       Impact factor: 8.739
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  3 in total

1.  Solid-Phase Synthesis of 5'-O-β,γ-Methylenetriphosphate Derivatives of Nucleosides and Evaluation of Their Inhibitory Activity Against HIV-1 Reverse Transcriptase.

Authors:  Yousef Ahmadibeni; Chandravanu Dash; Stuart F J Le Grice; Keykavous Parang
Journal:  Tetrahedron Lett       Date:  2010-06-02       Impact factor: 2.415

2.  Inhibition of multi-drug resistant HIV-1 reverse transcriptase by nucleoside β-triphosphates.

Authors:  Chandravanu Dash; Yousef Ahmadibeni; Michael J Hanley; Jui Pandhare; Mathias Gotte; Stuart F J Le Grice; Keykavous Parang
Journal:  Bioorg Med Chem Lett       Date:  2011-05-08       Impact factor: 2.823

3.  Synthesis of β-triphosphotriester pronucleotides.

Authors:  Yousef Beni; Chandravanu Dash; Keykavous Parang
Journal:  Tetrahedron Lett       Date:  2015-03-16       Impact factor: 2.415
  3 in total

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