Synthesis of Novel 6′-Spirocyclopropyl-5′-Norcarbocyclic Adenosine Phosphonic Acid Analogues as Potent Anti-Hiv Agents

REFERENCES

• Bisacchi , G. S. , Chao , S. T. , Bachard , C. , Daris , J. P. , Innaimo , S. , Jacobs , G. A. , Kocy , O. , Lapointe , P. , Martel , A. , Merchant , Z. , Slusarchyk , W. A. , Sundeen , J. E. , Young , M. G. , Colonno , R. and Zahler , R. 1997 . BMS-200475, a novel carbocyclic 2′-deoxyguanosine analog with potent and selective anti-hepatitis B virus activity in vitro . Bioorg. Med. Chem. Lett. , 7 : 127 – 132 .
   Web of Science ®Google Scholar
• Innaimo , S. F. , Seifer , M. , Bisacchi , G. S. , Standring , D. N. , Zahler , R. and Colonno , R. J. 1997 . Identification of BMS-200475 as a potent and selective inhibitor of hepatitis B virus . Antimicrob Agents Ch , 41 : 1444 – 1448 .
   PubMed Web of Science ®Google Scholar
• Katagiri , N. , Nomura , M. , Sato , H. , Kaneko , C. , Yusa , K. and Tsuruo , T. 1992 . Synthesis and anti-HIV activity of 9-[c-4,t-5-bis(hydroxymethyl)cyclopent-2-en-r-1-yl]-9H-adenine . J. Med. Chem. , 35 : 1882 – 1886 .
   PubMed Web of Science ®Google Scholar
• Jeong , L. S. and Yoo , S. J. 1998 . Synthesis and antiviral activity of novel isodideoxy nucleosides with exocyclic methylene . Bioorg. Med. Chem. Lett. , 8 : 847 – 852 .
   PubMed Web of Science ®Google Scholar
• Nair , V. , Mickle , T. and Bera , S. 2003 . Cyclopropyl and related analogs of the anti-HIV compound, isodideoxyadenosine . Nucleos. Nucleot. Nucl. , 22 : 239 – 247 .
   PubMed Web of Science ®Google Scholar
• Kim , C. U. , Luh , B. Y. , Misco , P. F. , Bronson , J. J. , Hitchcock , M. J. , Ghazzouli , I. and Martin , J. C. 1990 . Acyclic purine phosphonate analogues as antiviral agents. Synthesis and structure-activity relationships . J. Med. Chem , 33 : 1207 – 1213 .
   PubMed Web of Science ®Google Scholar
• Kim , C. U. , Luh , B. Y. and Martin , J. C. 1991 . Regiospecific and highly stereoselective electrophilic addition to furanoid glycals: synthesis of phosphonate nucleotide analogs with potent activity against HIV . J. Org. Chem. , 56 : 2642 – 2647 .
   Web of Science ®Google Scholar
• House , H. O. , Lord , R. C. and Rao , H. S.J. 1956 . The synthesis of spiropentane-d 8 . J. Org. Chem. , 21 : 1487 – 1491 .
   Web of Science ®Google Scholar
• Gosselck , J. and Schmidt , G. 1968 . A new route to 1,1-disubstituted cyclopropane . Angew. Chem. Int. Ed. , 7 : 456 – 457 .
   Web of Science ®Google Scholar
• Marco , J. L. and Hueso-Rodriquez , J. A. 1988 . Synthesis of optically pure 1-(3-furyl)-1,2-dihydroxyethane derivatives . Tetrahedron Lett , 29 : 2459 – 2462 .
   Google Scholar
• Mancuso , A. J. , Huang , S. L. and Swern , D. 1978 . Oxidation of long-chain and related alcohols to carbonyls by dimethyl sulfoxide “activated” by oxalyl chloride . J. Org. Chem. , 43 : 2480 – 2482 .
   Web of Science ®Google Scholar
• Ko , O. H. and Hong , J. H. 2002 . Efficient synthesis of novel carbocyclic nucleosides via sequential Claisen rearrangement and ring-closing metathesis . Tetrahedron Lett , 43 : 6399 – 6402 .
   Web of Science ®Google Scholar
• Jeong , L. S. and Lee , J. A. 2004 . Recent advances in the synthesis of the carbocyclic nucleosides as potential antiviral agents . Antiviral Chem. Chemother , 15 : 235 – 250 .
   PubMedGoogle Scholar
• Amblard , F. , Nolan , S. P. and Agrofoglio , L. A. 2005 . Metathesis strategy in nucleoside chemistry . Tetrahedron , 61 : 7067 – 7080 .
   Web of Science ®Google Scholar
• Tanaka , M. , Norimine , Y. , Fujita , T. , Suemune , H. and Sakai , K. 1996 . Chemoenzymatic Synthesis of antiviral carbocyclic nucleosides: asymmetric hydrolysis of meso-3,5-bis(acetoxymethyl)cyclopentenes using Rhizopus delemar lipase . J. Org. Chem. , 61 : 6952 – 6957 .
   PubMed Web of Science ®Google Scholar
• Liu , L. J. , Kim , S. W. , Lee , W. and Hong , J. H. 2009 . Selective ring-opening fluorination of epoxide: an efficient synthesis of 2′-C-fluoro-2′-C-methyl carbocyclic nucleosides . Bull. Korean Chem. Soc. , 30 : 2989 – 2992 .
   Web of Science ®Google Scholar
• Chong , Y. H. , Gumina , G. and Chu , C. K. 2000 . A divergent synthesis of D- and L-carbocyclic 4′-fluoro-2′,3′-dideoxynucleosides as potential antiviral agents . Tetrahedron: Asymmetry , 11 : 4853 – 4875 .
   Web of Science ®Google Scholar
• Oh , H. S. and Kang , H. Y. 2010 . Total synthesis of neomethymycin and novamethymycin . Tetrahedron , 66 : 4307 – 4317 .
   Web of Science ®Google Scholar
• Phillion , D. P. and Andrew , S. S. 1986 . Synthesis and reactivity of diethyl phosphonomethyltriflate . Tetrahedron Lett , 27 : 1477 – 1480 .
   Web of Science ®Google Scholar
• Xu , Y. , Flavin , M. T. and Xu , Z.-Q. 1996 . Preparation of new Wittig reagents and their application to the synthesis of α,β-unsaturated phosphonates . J. Org. Chem. , 61 : 7697 – 7701 .
   PubMed Web of Science ®Google Scholar
• Hocková , D. , Holý , A. , Masojídková , M. , Keough , D. T. , De Jersey , J. and Guddat , L. W. 2009 . Synthesis of branched 9-[2-(2-phosphonoethoxy)ethyl]purines as a new class of acyclic nucleoside phosphonates which inhibit Plasmodium falciparum hypoxanthine-guanine-xanthine phosphoribosyltransferase . Bioorg. Med. Chem. , 17 : 6218 – 6232 .
   PubMed Web of Science ®Google Scholar
• Koh , Y. H. , Shim , J. H. , Wu , J. Z. , Zhong , W. , Hong , Z. and Girardet , J. L. 2005 . Design, synthesis, and antiviral activity of adenosine 5′-phosphonate analogues as chain terminators against hepatitis C virus . J. Med. Chem , 48 : 2867 – 2875 .
   PubMed Web of Science ®Google Scholar
• Trost , B. M. , Kuo , G. H. and Benneche , T. 1988 . Transition-metal-controlled synthesis of (±)-aristeromycin and (±)-2′,3′-diepi-aristeromycin. An unusual directive effect in hydroxylations . J. Am. Chem. Soc. , 110 : 621 – 622 .
   Web of Science ®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
• Périgaud , C. , Gosselin , G. , Lefebvre , I. , Girardet , J. L. , Benzaria , S. , Barber , I. and Imbach , J. L. 1993 . Rational design for cytosolic delivery of nucleoside monphosphates: ‘SATE’ and ‘DTE’ as enzyme-labile transient phosphate protecting groups . Bioorg. Med. Chem. Lett. , 3 : 2521 – 2526 .
   Web of Science ®Google Scholar
• Lian , L. J. , Yoo , J. C. and Hong , J. H. 2009 . Short synthesis and antiviral activity of acyclic phosphonic acid nucleoside analogues . Nucleos. Nucleot. Nucl. , 28 : 150 – 164 .
   PubMed Web of Science ®Google Scholar