Design and Synthesis of Novel Carbocyclic Versions of 2′-spirocyclopropyl Ribonucleosides as Potent Anti-HCV Agents

REFERENCES

• Szabo , E. , Lotz , G. , Paska , C. , Kiss , A. and Schaff , Z. 2003 . Viral hepatitis: new data on hepatitis C infection . Pathol. Oncol. Res. , 9 : 215 – 221 .
   PubMed Web of Science ®Google Scholar
• Choo , Q. L. , Kuo , G. , Weiner , A. J. , Overby , L. R. , Bradley , D. W. and Houghton , M. 1989 . Isolation of a cDNA clone derived from a blood-borne non-A, non-B viral hepatitis genome . Science , 244 : 359 – 362 .
   PubMed Web of Science ®Google Scholar
• Hoofnagle , J. H. 1997 . Hepatitis C: the clinical spectrum of disease . Hepatology , 26 : 15S – 20S .
   PubMed Web of Science ®Google Scholar
• Hughes , C. A. and Shafran , S. D. 2006 . Treatment of hepatitis C in HIV-coinfected patients . Ann. Pharmacother. , 40 : 479 – 489 .
   PubMed Web of Science ®Google Scholar
• Chiacchio , U. , Borrello , L. , Crispino , L. , Rescifina , A. , Merino , P. , Macchi , B. , Balestrieri , E. , Mastino , A. , Piperno , A. and Romeo , G. 2009 . Stereoselective synthesis and biological evaluations of novel 3′-deoxy-4′-azaribonucleosides as inhibitors of hepatitis C virus RNA replication . J. Med. Chem , 52 : 4054 – 4057 .
   PubMed Web of Science ®Google Scholar
• Gunic , E. , Chow , S. , Rong , F. , Ramasamy , K. , Raney , A. , Li , D. Y. , Huang , J. , Hamatake , R. K. , Hong , Z. and Girardet , J. L. 2007 . 6-Hydrazinopurine 2′-methyl ribonucleosides and their 5′-monophosphate prodrugs as potent hepatitis C virus inhibitors . Bioorg. Med. Chem. Lett , 17 : 2456 – 2458 .
   PubMed Web of Science ®Google Scholar
• Koch , U. and Narjes , F. 2007 . Recent progress in the development of inhibitors of the hepatitis C virus RNA-dependent RNA polymerase . Curr. Top. Med. Chem , 7 : 1302 – 1329 .
   PubMed Web of Science ®Google Scholar
• Kim , H. J. , Sharon , A. , Bal , C. , Wang , J. , Allu , M. , Huang , Z. , Murray , M. G. , Bassit , L. , Schinazi , R. F. , Korba , B. and Chu , C. K. 2009 . Synthesis and anti-hepatitis B virus and anti-hepatitis C virus activities of 7-deazaneplanocin A analogues in vitro . J. Med. Chem , 52 : 206 – 213 .
   PubMed Web of Science ®Google Scholar
• Pierra , C. , Amador , A. , Benzaria , S. , Cretton-Scott , E. , D’Amours , M. , Mao , J. , Mathieu , S. , Moussa , A. , Bridges , E. G. , Standring , D. N. , Sommadossi , J. P. , Storer , R. and Gosselin , G. 2006 . Synthesis and pharmacokinetics of valopicitabine (NM283), an efficient prodrug of the potent anti-HCV agent 2′-C-methylcytidine . J. Med. Chem. , 49 : 6614 – 6620 .
   PubMed Web of Science ®Google Scholar
• Eldrup , A. B. , Allerson , C. R. , Bennett , C. F. , Bera , S. , Bhat , B. , Bhat , N. , Bosserman , M. R. , Brooks , J. , Burlein , C. , Carrol , S. S. , Cook , P. D. , Getty , K. L. , MacCross , M. , McMasters , D. R. , Olsen , D. B. , Prakash , T. P. , Prhavc , M. , Song , Q. L. , Tomassini , J. E. and Xia , J. 2004 . Structure-activity relationship of purine ribonucleosides for inhibition of hepatitis C virus RNA-dependent RNA polymerase . J. Med. Chem. , 47 : 2283 – 2295 .
   PubMed Web of Science ®Google Scholar
• Clark , J. L. , Hollecker , L. , Mason , J. C. , Stuyver , L. J. , Tharnish , P. M. , Lostia , S. , McBrayer , T. R. , Schinazi , R. F. , Watanabe , K. A. , Otto , M. J. , Furman , P. A. , Stec , W. J. , Patterson , S. E. and Pankiewicz , K. W. 2005 . Design, synthesis, and antiviral activity of 2′-deoxy-2′-fluoro-2′-C-methylcytidine, a potent inhibitor of hepatitis C virus replication . J. Med. Chem , 48 : 5504 – 5508 .
   PubMed Web of Science ®Google Scholar
• Jonckers , T. H. , Lin , T. I. , Buyck , C. , Lachau–Durand , S. , Vandyck , K. , Van Hoof , S. , Vandekerckhove , L. A. , Hu , L. , Berke , J. M. , Vijgen , L. , Dillen , L. L. , Cummings , M. D. , de Kock , H. , Nilsson , M. , Sund , C. , Rydegård , C. , Samuelsson , B. , Rosenquist , A. , Fanning , G. , Van Emelen , K. , Simmen , K. and Raboisson , P. 2010 . 2′-Deoxy-2′-spirocyclopropylcytidine revisited: a new and selective inhibitor of the hepatitis C virus NS5B polymerase . J. Med. Chem. , 53 : 8150 – 8160 .
   PubMed Web of Science ®Google Scholar
• Boojamra , C. G. , Parrish , J. P. , Sperandio , D. , Gao , Y. , Petrakovsky , O. V. , Lee , S. K. , Markevich , D. Y. , Vela , J. E. , Laflamme , G. , Chen , J. M. , Ray , A. S. , Barron , A. C. , Sparacino , M. L. , Desai , M. C. , Kim , C. U. , Cihlar , T. and Mackman , R. L. 2009 . Design, synthesis, and anti-HIV activity of 4′-modified carbocyclic nucleoside phosphonate reverse transcriptase inhibitors . Bioorg. Med. Chem. , 17 : 1739 – 1746 .
   PubMed Web of Science ®Google Scholar
• Smith , D. B. , Kalayanov , G. , Sund , C. , Winqvist , A. , Maltseva , T. , Leveque , V. J. , Rajyaguru , S. , Pogam , S. L. , Najera , I. , Benkestock , K. , Zhou , X. X. , Kaiser , A. C. , Maag , H. , Cammack , N. , Martin , J. A. , Swallow , S. , Johansson , N. G. , Klumpp , K. and Smith , M. 2009 . The design, synthesis, and antiviral activity of 4′-azidocytidine analogues against hepatitis C virus replication: the discovery of 4′-azidoarabinocytidine . J. Med. Chem. , 52 : 219 – 223 .
   PubMed Web of Science ®Google Scholar
• Li , H. , Baik , Y. C. and Hong , J. H. 2009 . Synthesis of 3′(β)-C-methyl carbodine analogues as potential anti-HCV agents . Bull. Korean Chem. Soc , 30 : 1147 – 1151 .
   Web of Science ®Google Scholar
• Ruder , S. M. and Ronald , R. C. 1984 . 2-Chloroethyl dimethyl sulfonium iodide. A convenient reagent for spiroannelation of ketones . Tetrahedron Lett , 25 : 5501 – 5504 .
   Web of Science ®Google Scholar
• Kigoshi , H. , Imamura , Y. , Mizuta , K. , Niwa , H. and Yamada , K. 1993 . Total synthesis of natural (−)-ptaquilosin, the aglycon of a potent bracken carcinogen ptaquiloside, and the (+)-enantiomer and their DNA cleaving activities . J. Am. Chem. Soc. , 115 : 3056 – 3065 .
   Web of Science ®Google Scholar
• Yates , P. , Helferty , P. H. and Mahler , P. 1983 . Nucleophilic and acid-catalyzed cleavage of the cyclopropan rings of β,γ-unsaturated α-spirocyclopropyl ketones . Can. J. Chem. , 61 : 78 – 85 .
   Web of Science ®Google Scholar
• Yin , X. Q. , Li , W. K. , Yang , M. and Schneller , S. W. 2009 . A new synthesis and an antiviral assessment of the 4′-fluoro derivative of 4′-deoxy-5′-noraristeromycin . Bioorg. Med. Chem. , 17 : 3126 – 3129 .
   PubMed Web of Science ®Google Scholar
• Sisu , E. , Sollogoub , M. , Mallet , J. M. and Sinay , P. 2002 . Cycloheptanic sugar mimetics, bridging the gap in the homologous series of carbocyclic analogues . Tetrahedron , 58 : 10189 – 10196 .
   Web of Science ®Google Scholar
• Takaku , H. , Kamaike , K. and Tsuchiya , H. 1984 . Synthesis of ribooligonucleotides using the 4-methoxybenzyl group as a new protecting group for the 2’-hydroxyl group . J. Org. Chem. , 49 : 51 – 56 .
   Web of Science ®Google Scholar
• Horita , K. , Yoshioka , T. , Tanaka , T. , Oikawa , Y. and Yonemitsu , O. 1986 . On the selectivity of deprotection of benzyl, mpm (4-methoxybenzyl) and dmpm (3,4-dimethoxybenzyl) protecting groups for hydroxy functions . Tetrahedron , 42 : 3021 – 3028 .
   Web of Science ®Google Scholar
• Oikawa , Y. , Tanaka , T. , Horita , K. and Yonemitsu , O. 1984 . Selective hydrogenolysis of the benzyl protecting group for hydroxy function with raney nickel in the presence of the MPM (4-methoxybenzyl) and DMPM (3,4-dimethoxybenzyl) protecting groups . Tetrahedron Lett. , 25 : 5397 – 5400 .
   Web of Science ®Google Scholar
• Pathak , T. , Bazin , H. and Chattopadhyaya , J. 1986 . Synthesis of 2′-deoxy-2′(S)-deuterio and 2′-deoxy-2′(R)-deuterio-β-D-nucleosides . Tetrahedron , 42 : 5427 – 5441 .
   Web of Science ®Google Scholar
• Revankar , G. R. , Gupta , P. K. , Adams , A. D. , Dalley , N. K. , McKernan , P. A. , Cook , P. D. , Canonico , P. G. and Robins , R. K. 1984 . Synthesis and antiviral/antitumor activities of certain 3-deazaguanine nucleosides and nucleotides . J. Med Chem. , 27 : 1389 – 1396 .
   PubMed Web of Science ®Google Scholar
• Leonard , N. J. and Laursen , R. A. 1963 . The synthesis of 3-β-D-ribofuranosyl adenine . J. Am. Chem. Soc. , 85 : 2026 – 2028 .
   Web of Science ®Google Scholar
• Liu , L. J. and Hong , J. H. 2009 . Synthesis and anti-hepatitis C virus activity of 2′(β)-hydroxyethyl and 4′(α)-hydroxymethyl carbodine analogues . Nucleosides Nucleotides Nucleic Acids , 28 : 1007 – 1015 .
   PubMed Web of Science ®Google Scholar