TY  - JOUR
  - Debarge, S,Balzarini, J,Maguire, AR
  - 2011
  - January
  - The Journal of Organic Chemistry
  - Design and Synthesis of alpha-Carboxy Phosphononucleosides
  - Validated
  - ()
  - H INSERTION REACTIONS ANTI-HIV ACTIVITY ACYCLIC NUCLEOSIDE PHOSPHONATES CARBENOID MEDIATED CYCLIZATIONS TERT-BUTYLDIMETHYLSILYL GROUP OF-THE-ART REVERSE-TRANSCRIPTASE BIOLOGICAL-ACTIVITY DNA-POLYMERASES CYCLIC ETHERS
  - 76
  - 105
  - 126
  - Rhodium catalyzed O-H insertion reactions employing alpha-diazophosphonate 20 with appropriately protected thymidine, uridine, cytosine, adenosine and guanosine derivatives leads to novel 5'-phosphononucleoside derivatives. Deprotection led to a novel series of phosphono derivatives bearing a carboxylic acid moiety adjacent to the phosphonate group with potential antiviral and/or anticancer activity. The phosphononucleosides bearing an alpha-carboxylic acid group are envisaged as potential diphosphate mimics. Conversion to mono- and diphosphorylated phosphononucleosides has been effected for evaluation as nucleoside triphosphate mimics. Most of the novel phosphononucleosides proved to be inactive against a variety of DNA and RNA viruses. Only the phosphono AZT derivatives 56-59 showed weak activity against HIV-1 and HIV-2.
  - DOI 10.1021/jo101738e
DA  - 2011/01
ER  - 

@article{V70046417,
   = {Debarge,  S and Balzarini,  J and Maguire,  AR },
   = {2011},
   = {January},
   = {The Journal of Organic Chemistry},
   = {Design and Synthesis of alpha-Carboxy Phosphononucleosides},
   = {Validated},
   = {()},
   = {H INSERTION REACTIONS ANTI-HIV ACTIVITY ACYCLIC NUCLEOSIDE PHOSPHONATES CARBENOID MEDIATED CYCLIZATIONS TERT-BUTYLDIMETHYLSILYL GROUP OF-THE-ART REVERSE-TRANSCRIPTASE BIOLOGICAL-ACTIVITY DNA-POLYMERASES CYCLIC ETHERS},
   = {76},
  pages = {105--126},
   = {{Rhodium catalyzed O-H insertion reactions employing alpha-diazophosphonate 20 with appropriately protected thymidine, uridine, cytosine, adenosine and guanosine derivatives leads to novel 5'-phosphononucleoside derivatives. Deprotection led to a novel series of phosphono derivatives bearing a carboxylic acid moiety adjacent to the phosphonate group with potential antiviral and/or anticancer activity. The phosphononucleosides bearing an alpha-carboxylic acid group are envisaged as potential diphosphate mimics. Conversion to mono- and diphosphorylated phosphononucleosides has been effected for evaluation as nucleoside triphosphate mimics. Most of the novel phosphononucleosides proved to be inactive against a variety of DNA and RNA viruses. Only the phosphono AZT derivatives 56-59 showed weak activity against HIV-1 and HIV-2.}},
   = {DOI 10.1021/jo101738e},
  source = {IRIS}
}