Design and Synthesis of Novel Sate Derivatives of Acyclic Isocytosine and 9-Deazaadenine C-Nucleosides

REFERENCES

• De Clercq , E. , Holý , A. , Rosenberg , I. , Sakuma , T. , Balzarini , J. and Maudgal , P. C. 1986 . A novel selective broad-spectrum anti-DNA virus agent . Nature , 323 : 464 – 467 .
   PubMed Web of Science ®Google Scholar
• De Clercq , E. 2002 . Codofovir in the treatment of poxvirus infections . Antiviral Res. , 55 : 1 – 13 .
   PubMed Web of Science ®Google Scholar
• Robbins , B. L. , Srinivas , R. V. , Kim , C. , Bischofberger , N. and Fridland , A. 1998 . Anti-human immunodeficiency virus activity and cellular metabolism of a potential prodrug of the acyclic nucleoside phosphonate 9-R-(2-phosphonomethoxypropyl)adenine (PMPA), Bis(isopropyloxymethylcarbonyl)PMPA . Antimicrob. Agents Chemother. , 2 : 612 – 617 .
   Google Scholar
• Vandendriessche , F. , Snoeck , R. , Janssen , G. , Hoogmartens , J. , Van Aerschot , A. , De Clercq , E. and Herdewijn , P. 1992 . Synthesis and antiviral activity of acyclic nucleosides with a 3(S),5-dihydroxypentyl or 4(R)-methoxy-3(S),5-dihydroxypentyl side chain . J. Med. Chem. , 35 : 1458 – 1465 .
   PubMed Web of Science ®Google Scholar
• Liu , L. J. , Yoo , J. C. and Hong , J. H. 2009 . Short synthesis and antiviral activity of acyclic phosphonic acid nucleoside analogues . Nucleosides Nucleotides Nucleic Acids , 28 : 150 – 164 .
   PubMed Web of Science ®Google Scholar
• Topalis , D. , Alvarez , K. , Barral , K. , Munier-Lehmann , H. , Schneider , B. , Véron , M. , Guerreiro , C. , Mulard , L. , El-Amri , C. , Canard , B. and Deville-Bonne , D. 2008 . Acyclic phosphonate nucleotides and human adenylate kinases: impact of a borano group on alpha-P position . Nucleosides Nucleotides Nucleic Acids , 27 : 319 – 331 .
   PubMed Web of Science ®Google Scholar
• Naesens , L. , Balzarini , J. and De Clercq , E. 1994 . Therapeutic potential of PMEA as an antiviral drug . Med. Virol. , 4 : 147 – 159 .
   Google Scholar
• De Clercq , E. 1991 . Broad-spectrum anti-DNA virus and anti-retrovirus activity of phosphonylmethoxyalkylpurines and pyrimidines . Biochem. Pharmacol. , 42 : 963 – 972 .
   PubMed Web of Science ®Google Scholar
• Pauwels , R. , Balzarini , J. , Schols , D. , Baba , M. , Desmyter , J. , Rosenberg , I. , Holy , A. and De Clercq , E. 1988 . Phosphonylmethoxyethyl purine derivatives, a new class of anti-human immunodeficiency virus agents . Antimicrob Agents Chemother. , 32 : 1025 – 1030 .
   PubMed Web of Science ®Google Scholar
• De Clercq , E. 2003 . Potential of acyclic nucleoside phosphonates in the treatment of DNA virus and retrovirus infections . Expert. Rev. Anti. Infect. Ther. , 1 : 21 – 43 .
   PubMedGoogle Scholar
• Görbig , U. , Balzarini , J. and Meier , C. 2007 . New cycloAmb-nucleoside phosphonate prodrugs . Nucleosides Nucleotides Nucleic Acids , 26 : 831 – 834 .
   PubMed Web of Science ®Google Scholar
• Starrett , J. E. Jr. , Tortolani , D. R. , Hitchcock , M. J.M. , Martin , J. C. and Mansuri , M. M. 1992 . Synthesis and in vivo evaluation of a phosphonate prodrug: bis(pivaloylosymethyl) 9-(2-phosphonylmethoxyethyl) adenine . Antiviral Res. , 19 : 267 – 273 .
   PubMed Web of Science ®Google Scholar
• Puech , F. , Gosselin , G. , Lefebvre , I. , Pompon , A. , Aubertin , A. M. , Kirn , A. and Imbach , J. L. 1993 . Intracellular delivery of nucleoside monophosphates through a reductase-mediated activation process . Antiviral Res. , 22 : 155 – 174 .
   PubMed Web of Science ®Google Scholar
• Benzaria , S. , Pélicano , H. , Johnson , R. , Maury , G. , Imbach , J. L. , Aubertin , A. M. , Obert , G. and Gosselin , G. 1996 . Synthesis, in vitro antiviral evaluation, and stability studies of bis(S-acyl-2-thio-ethyl) ester derivatives of 9-(2-phosphonomethoxy) ethyladenine (PMEA) as potential PMEA prodrugs with improved oral bioavailability . J. Med. Chem. , 39 : 4958 – 4965 .
   PubMed Web of Science ®Google Scholar
• Zelinskii , N. D. and Uyedinov , M. N. 1913 . 1,1-Dimethy cyclobutane . Ber. , 46 : 1093 – 1094 .
   Google Scholar
• Kim , A. and Hong , J. H. 2005 . Synthesis and anti-HCMV activity of novel 5′-norcarboacyclic nucleosides . Arch. Pharm. , 338 : 522 – 527 .
   PubMed Web of Science ®Google Scholar
• Tanaka , T. , Tamatsukuri , S. and Ikehara , M. 1986 . New approach to the synthesis of deoxynucleoside phosphoramidite derivatives . Tetrahedron Lett. , 27 : 199 – 202 .
   Web of Science ®Google Scholar
• Perich , J. W. and Hohn , R. B. 1987 . Di-tert-butyl N,N-diethyl phosphoramidite. A new phosphitylating agent for the efficient phosphorylation of alcohol . Synthesis , : 142 – 144 .
   Google Scholar
• Lefebvre , I. , Périgaud , C. , Pompon , A. , Aubertin , A. M. , Girardet , J. L. , Kirn , A. , Gosselin , G. and Imbach , J. L. 1995 . Mononucleoside phosphotriester derivatives with S-acyl-2-thioethyl bioreversible phosphate-protecting groups: Intracellular delivery of 3′-azido-2′,3′-dideoxythymidine 5′-monophosphate . J. Med. Chem. , 38 : 3941 – 3950 .
   PubMed Web of Science ®Google Scholar
• Kamath , V. P. , Ananth , S. , Bantia , S. and Morris , P. E. 2004 . Synthesis of a potent transit-state inhibitor of 5′-deoxy-5′-methylthioadenosine phosphorylase . J. Med. Chem. , 47 : 1322 – 1324 .
   PubMed Web of Science ®Google Scholar