Synthesis and Biological Evaluation of 2′,3′-Didehydro-2′,3′-Dideoxy-9-Deazaguanosine, a Monophosphate Prodrug and Two Analogues, 2′,3′-Dideoxy-9-Deazaguanosine and 2′,3′-Didehydro-2′,3′-Dideoxy-9-Deazainosine

References

• Bzowska , A .; Kulikowska , E .; Shugar , D . Purine nucleoside phosphorylases: properties, functions, and clinical aspects . Pharmacol. Ther . 2000 , 88 , 349 – 425 . [PUBMED] [INFOTRIEVE] [CSA]
   PubMed Web of Science ®Google Scholar
• Marquez , V . E .; Tseng , C . K.-H .; Mitsura , H .; Aoik , S .; Kelley , J . A .; Ford , H ., Jr .; Roth , J . S .; Broder , S .; Johns , D . G .; Driscoll , J . S . Acid-stable 2′-fluoro purine dideoxynucleosides as active agents against HIV . J. Med. Chem . 1990 , 33 ( 3 ), 978 – 985 . [PUBMED] [INFOTRIEVE] [CSA] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Parks , R . E ., Jr .; Stoeckler , J . D .; Cambor , C .; Savarese , T . M .; Crabtree , G . W .; Chu , S.-H . Purine nucleoside phosphorylase and 5-methylthioadenosine phosphorylase: targets of chemotherapy . In Molecular Actions and Targets for Cancer Chemotherapeutic Agents ; Sartorelli , A . C ., Lazo , J . S ., Bertino , J . R ., Eds.; Academic : New York , 1981 ; 229 – 252 .
   Google Scholar
• Chu , M . Y .; Zuckerman , L . B .; Sato , S .; Crabtree , G . W .; Bogden , A . E .; Lim , M.-I .; Klein , R . S . 9-Deazaadenosine—a new potent antitumor agent . Biochem. Pharmacol . 1984 , 33 ( 8 ), 1229 – 1234 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMedGoogle Scholar
• Glazer , R . I .; Hartman , K . D .; Knode , M . C . 9-Deazaadenosine. Cytocidal activity and effects on nucleic acids and protein synthesis in human colon carcinoma cells in culture . Mol. Pharmacol . 1983 , 24 , 309 – 315 . [PUBMED] [INFOTRIEVE]
   PubMed Web of Science ®Google Scholar
• Marr , J . J .; Berens , R . L .; Cohn , N . K .; Nelson , D . J .; Klein , R . S . Biological action of inosine analogs in Leishmania and Trypanosoma spp . Antimicrob. Agents Chemother . 1984 , 25 ( 2 ), 292 – 295 . [PUBMED] [INFOTRIEVE] [CSA]
   PubMedGoogle Scholar
• Fish , W . R .; Marr , J . J .; Berens , R . L .; Looker , D . L .; Nelson , D . J .; LaFon , S . W .; Balber , A . E . Inosine analogs as chemotherapeutic agents for African trypanosomes: metabolism in trypanosomes and efficacy in tissue culture . Antimicrob. Agents Chemother . 1985 , 27 ( 1 ), 33 – 36 . [PUBMED] [INFOTRIEVE] [CSA]
   PubMed Web of Science ®Google Scholar
• Vince , R .; Hua , M .; Brownell , J .; Daluge , S .; Lee , F .; Shannon , W . M .; Lavelle , G . C .; Qualls , J .; Weislow , O . S .; Kiser , R .; Canonico , P . G .; Schultz , R . H .; Narayanan , V . L .; Mayo , J . G .; Shoemaker , R . H .; Boyd , M . R . Potent and selective activity of a new carbocyclic nucleoside analog (Carbovir: NSC 614846) against human immunodeficiency virus in vitro . Biochem. Biophys. Res. Commun . 1988 , 156 ( 2 ), 1046 – 1053 . [PUBMED] [INFOTRIEVE]
   PubMedGoogle Scholar
• Daluge , S . M .; Good , S . S .; Faletto , M . B .; Miller , W . H .; St. Clair , M . H .; Boone , L . R .; Tisdale , M .; Parry , N . R .; Reardon , J . E .; Dornsife , R . E .; Averett , D . R .; Krenitsky , T . A . 1592U89, A novel carbocyclic nucleoside analog with potent, selective anti-human immunodeficiency virus activity . Antimicrob. Agents Chemother . 1997 , 41 ( 5 ), 1082 – 1093 . [PUBMED] [INFOTRIEVE] [CSA]
   PubMed Web of Science ®Google Scholar
• Faletto , M . B .; Miller , W . H .; Garvey , E . P .; St. Clair , M . H .; Daluge , S . M .; Good , S . S . Unique intracellular activation of the potent anti-human immunodeficiency virus agent 1592U89 . Antimicrob. Agents Chemother . 1997 , 41 ( 5 ), 1099 – 1107 . [PUBMED] [INFOTRIEVE] [CSA]
   PubMed Web of Science ®Google Scholar
• Chu , C . K .; Bhadti , V . S .; Doboszewski , B .; Gu , Z . P .; Kosugi , Y .; Pullaiah , K . C .; Van Roey , P . General syntheses of 2′,3′-dideoxynucleosides and 2′,3′-didehydro-2′,3′-dideoxynucleosides . J. Org. Chem . 1989 , 54 ( 9 ), 2217 – 2225 . [CROSSREF]
   Web of Science ®Google Scholar
• Mansuri , M . M .; Starrett , J . E ., Jr .; Wos , J . A .; Tortolani , D . R .; Brodfuehrer , P . R .; Howell , H . G .; Martin , J . C . Preparation of 1-(2,3-dideoxy-β-d-glycero-pent-2-enofuranosyl)thymine (d4T) and 2′,3′-dideoxyadenosine (ddA): general methods for the synthesis of 2′,3′-olefinic and 2′,3′-dideoxy nucleoside analogues active against HIV . J. Org. Chem . 1989 , 54 ( 20 ), 4780 – 4785 . [CROSSREF]
   Google Scholar
• Chen , C.-S .; Chern , J.-W . Nucleosides VIII: synthesis of 2′,3′-dideoxy- and 2′,3′-didehydro-2′,3′-dideoxyisoguanosine as potential antiretroviral agents . Nucleosides Nucleotides 1996 , 15 ( 7&8 ), 1253 – 1261 .
   Google Scholar
• Jain , T . C .; Jenkins , I . D .; Russell , A . F .; Verheyden , J . P.H .; Moffatt , J . G . Reactions of 2-acyloxyisobutyryl halides with nucleosides. IV. A facile synthesis of 2′,3′-unsaturated nucleosides using chromous acetate . J. Org. Chem . 1974 , 39 ( 1 ), 30 – 38 . [CROSSREF]
   Web of Science ®Google Scholar
• Bhat , V .; Stocker , E .; Ugarkar , B . G . A new synthesis of 2′,3′-dideoxyinosine . Synth. Commun . 1992 , 22 ( 10 ), 1481 – 1486.
   Web of Science ®Google Scholar
• Liu , M.-C .; Luo , M.-Z .; Mozdziesz , D . E .; Sartorelli , A . C . Synthesis and biological evaluation of 2- and 7-substituted 9-deazaadenosine analogues . Nucleosides Nucleotides Nucleic Acids 2005 , 24 ( 1 ), 45 – 62 . [PUBMED] [INFOTRIEVE]
   PubMed Web of Science ®Google Scholar
• McGuigan , C .; Pathirana , R . N .; Mahmood , N .; Devine , K . G .; Hay , A . J . Aryl phosphate derivatives of AZT retain activity against HIV1 in cell lines which are resistant to the action of AZT . Antiviral Res . 1992 , 17 , 311 – 321 . [PUBMED] [INFOTRIEVE] [CSA] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Francom , P .; Janeba , Z .; Shibuya , S .; Robins , M . J . Nucleic acid related compounds. 116. Nonaqueous diazotization of aminopurine nucleosides. Mechanistic considerations and efficient procedures with tert-butyl nitrite or sodium nitrite . J. Org. Chem . 2002 , 67 ( 19 ), 6788 – 6796 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMedGoogle Scholar
• Glaser , R .; Rayat , S .; Lewis , M .; Son , M.-S .; Meyer , S . Theoretical studies of DNA base deamination. 2. Ab initio study of DNA base diazonium ions and of their linear, unimolecular dediazonation paths . J. Am. Chem. Soc . 1999 , 121 ( 26 ), 6108 – 6119 . [CROSSREF]
   Google Scholar
• Lin , T.-S .; Luo , M.-Z .; Liu , M.-C .; Pai , S . B .; Dutschman , G . E .; Cheng , Y.-C . Synthesis and biological evaluation of 2′,3′-dideoxy-l-pyrimidine nucleosides as potential antiviral agents against human immunodeficiency virus (HIV) and hepatitis B virus . J. Med. Chem . 1994 , 37 ( 6 ), 798 – 803 . [PUBMED] [INFOTRIEVE] [CSA] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Rao , T . S .; Lewis , A . F .; Hill , T . S .; Revankar , G . R . Incorporation of 2′-deoxy-9-deazaguanosine and 2′-deoxy-7-deaza-6-thioguanosine into G-rich oligodeoxyribonucleotides . Nucleosides Nucleotides 1995 , 14 ( 1&2 ), 1 – 12 .
   Google Scholar