A Rapid Synthetic Route to Conformationally Restricted [5,5]-Bicyclic Nucleoside-Amino Acid Conjugates

REFERENCES AND NOTES

• Meunier , B. 2007 . Hybrid molecules with a dual mode of action: dream or reality? . Acc. Chem. Res. , For some recent publications, see; ACS ASAP (DOI: 10.1021/ar7000843)
   PubMed Web of Science ®Google Scholar
• Decker and Recent , M. 2007 . advances in the development of hybrid molecules/designed multiple compounds with antiamnesic properties . Rev. Med. Chem. , 7 : 221 – 229 .
   PubMed Web of Science ®Google Scholar
• Baraldi , P.G. , Preti , D. , Fruttarolo , F. , Tabrizi , M. A. and Romagnoli , R. 2007 . Hybrid molecules between distamycin A and active moieties of antitumor agents . Bioorg. Med. Chem. , 15 : 17 – 359 .
   PubMed Web of Science ®Google Scholar
• Viegas-Junior , C. , Danuello , A. , da Silva , B.V. , Barreiro , E. J. and Fraga , C.A M. 2007 . Molecular hybridization: a useful tool in the design of new drug prototypes . Curr. Med. Chem. , 14 : 1829 – 1852 .
   PubMed Web of Science ®Google Scholar
• Romagnoli , R. , Baraldi , P. G. , Carrion , M. D. , Cruz-Lopez , O. , Preti , D. , Tabrizi , M. A. , Fruttarolo , F. , Heilmann , J. , Bermejo , J. and Estevez , F. 2007 . Hybrid molecules containing benzo[4,5]imidazo[1,2-d][1,2,4]thiadiazole and α -bromoacryloyl moieties as potent apoptosis inducers on human myeloid leukemia cells . Bioorg. Med. Chem. Lett. , 17 : 2844 – 2848 .
   PubMed Web of Science ®Google Scholar
• Ohshita , K. , Ishiyama , H. , Oyanagi , K. , Nakata , H. and Kobayashi , J. 2007 . Synthesis of hybrid molecules of caffeine and eudistomin D and its effects on adenosine receptors . Bioorg. Med. Chem. , 15 : 3235 – 3240 .
   PubMed Web of Science ®Google Scholar
• Sturm , M.B. , Roday , S. and Schramm , V. L. 2007 . Circular DNA and DNA/RNA hybrid molecules as scaffolds for ricin inhibitor design . J. Am. Chem. Soc. , 129 : 5544 – 5550 .
   PubMed Web of Science ®Google Scholar
• Adamec , J. , Beckert , R. , Weiss , D. , Klimesova , V. , Waisser , K. , Moellmann , U. , Kaustova , J. and Buchta , V. 2007 . Hybrid molecules of estrone: New compounds with potential antibacterial, antifungal, and antiproliferative activities . Bioorg. Med. Chem. , 15 : 2898 – 2906 .
   PubMed Web of Science ®Google Scholar
• Wojciechowski , F. and Hudson , R.H.E. 2007 . Nucleobase modifications in peptide nucleic acids . Curr. Topics Med. Chem. , 7 : 667 – 679 .
   PubMed Web of Science ®Google Scholar
• Howarth , N.M. 2006 . Recent advances in the field of peptide nucleic acids . Lett. Org. Chem. , 3 : 495 – 503 .
   Google Scholar
• Nielsen , P.E. 2004 . The many faces of PNA . Lett. Peptide Sci. , 10 : 135 – 147 .
   Google Scholar
• de Koning , M.C. , van der Marel , G.A. and Overhand , M. 2003 . Synthetic developments towards PNA-peptide conjugates . Curr. Opin. Chem. Biol. , 7 : 734 – 740 .
   PubMed Web of Science ®Google Scholar
• Choi , Y. , Moon , H.R. , Yoshimura , Y. and Marquez , V.E. 2003 . Recent advances in the synthesis of conformationally locked nucleosides and their success in probing the critical question of conformational preferences by their biological targets . Nucleosides, Nucleotides Nucleic Acids , 22 : 547 – 557 . For some recent reports, see
   PubMed Web of Science ®Google Scholar
• Leumann , C.J. 2002 . DNA analogues: From supramolecular principles to biological properties . Bioorg. Med. Chem. , 10 : 841 – 854 .
   PubMed Web of Science ®Google Scholar
• Imanishi , T. and Obika , S. 2002 . BNAs: Novel nucleic acid analogs with a bridged sugar moiety . Chem. Commun. , : 1653 – 1659 .
   PubMed Web of Science ®Google Scholar
• Meldgaard , M. and Wengel , J. 2000 . Bicyclic nucleosides and conformational restriction of oligonucleotides . J. Chem. Soc., Perkin Trans , 1 : 3539 – 3554 .
   Google Scholar
• 1999 . Herdewijn Conformationally, P. restricted carbohydrate-modified nucleic acids and antisense technology . Biochim. Biophys. Acta. , 1489 : 167 – 179 .
   PubMed Web of Science ®Google Scholar
• Kool , E.T. 1997 . Preorganization of DNA: Design principles for improving nucleic acid recognition by synthetic oligonucleotides . Chem. Rev. , 97 : 1473 – 1487 .
   PubMed Web of Science ®Google Scholar
• Park , A.-Y. , Moon , H.R. , Kim , K.R. , Chun , M.W. and Jeong , L.S. 2006 . Synthesis of novel L-N-MCd4T as a potent anti-HIV agent . Org. Biomol. Chem. , 4 : 4065 – 4067 . For representative publications, see
   PubMed Web of Science ®Google Scholar
• De Clercq Antiviral , E. 2004 . drugs in current clinical use . J. Clin. Virol. , 30 : 115 – 133 .
   PubMed Web of Science ®Google Scholar
• Matsuda , A. and Sasaki , T. 2004 . Antitumor activity of sugar-modified cytosine nucleosides . Cancer Sci. , 95 : 105 – 111 .
   PubMed Web of Science ®Google Scholar
• Vester , B. and Wengel , J. 2004 . LNA (Locked Nucleic Acid): High-Affinity Targeting of Complementary . RNA and DNA Biochemistry , 43 : 13233 – 13241 .
   PubMed Web of Science ®Google Scholar
• Jepsen , J.S. , SØrensen , M.D. and Wengel , J. 2004 . Locked nucleic acid: A potent nucleic acid analog in therapeutics and biotechnology . Oligonucleotides , 14 : 130 – 146 .
   PubMed Web of Science ®Google Scholar
• Russ , P. , Schelling , P. , Scapozza , L. , Folkers , G. , De Clercq , E. and Marquez , V. E. 2003 . Synthesis and biological evaluation of 5-substituted derivatives of the potent antiherpes agent (north)-methanocarbathymine . J. Med. Chem. , 46 : 5045 – 5054 .
   PubMed Web of Science ®Google Scholar
• Shin , K.J. , Moon , H. R. , Georgen , C. and Marquez , V. E. 2000 . Construction of the bicyclo[3.1.0]hexane template of a conformationally locked carbocyclic adenosine via an olefin keto-carbene cycloaddition . J. Org. Chem. , 65 : 2172 – 2178 .
   PubMed Web of Science ®Google Scholar
• Molas , M.P. , Matheu , M. I. , Castillon , S. , Isac-Garcia , J. , Hernandez-Mateo , F. , Calvo-Flores , F.G. and Santoyo-Gonzalez . 1999 . Synthesis F. of 3,6-anhydro sugars from cyclic sulfites and sulfates and their applications in the preparation of bicyclo nucleoside analogs of ddC and ddA . Tetrahedron , 55 : 14649 – 14664 .
   Web of Science ®Google Scholar
• Agrofoglio , L.A. and Challand , S. R. 1998 . Acyclic, Carbocyclic and L-Nucleosides , Dordrecht : Kluwer Academic Publisher .
   Google Scholar
• Huryn , D. M. and Okabe , M. 1992 . AIDS-driven nucleoside chemistry . Chem. Rev. , 92 : 1745 – 1768 .
   Web of Science ®Google Scholar
• Tripathi , S. , Roy , B.G. , Drew , M.G.B. , Achari , B. and Mandal , S.B. 2007 . Synthesis of oxepane ring containing monocyclic, conformationally restricted bicyclic and spirocyclic nucleosides from D-glucose: A cycloaddition approach . J. Org. Chem. , 72 : 7427 – 7430 . For recent examples, see
   PubMed Web of Science ®Google Scholar
• Albæk , N. , Petersen , M. and Nielsen , P. 2006 . Analogues of a locked nucleic acid with three-carbon 2′,4′-linkages: synthesis by ring-closing metathesis and influence on nucleic acid duplex stability and structure . J. Org. Chem. , 71 : 7731 – 7740 .
   PubMed Web of Science ®Google Scholar
• Kumar , S.T. , Madsen , A. S. , Wengel , J. and Hrdlicka , P. J. 2006 . Synthesis and hybridization studies of 2′-amino-α -L-LNA and tetracyclic “locked LNA” . J. Org. Chem. , 71 : 4188 – 4201 .
   PubMed Web of Science ®Google Scholar
• Gagneron , J. and Gosselin , G. 2006 . Mathé. Synthesis and conformational analysis of 4′-modified (2-oxabicyclo-[3.1.0]hexyl)pyrimidine nucleosides . Eur. J. Org. Chem. , : 4891 – 4897 .
   Web of Science ®Google Scholar
• Sekiguchi , M. , Obika , S. , Harada , Y. , Osaki , T. , Somjing , R. , Mitsuoka , Y. , Shibata , N. , Masaki , M. and Imanishi , T. 2006 . Synthesis and properties of trans-3′,4′-bridged nucleic acids having typical S-type sugar conformation . J. Org. Chem. , 71 : 1306 – 1316 .
   PubMed Web of Science ®Google Scholar
• Gagneron , J. and Gosselin , G. 2005 . Mathé. Synthesis of nucleoside analogs bearing the five naturally occurring nucleic acid bases built on a 2-oxabicylo[3.1.0]hexane scaffold . J. Org. Chem. , 70 : 6891 – 6897 .
   PubMed Web of Science ®Google Scholar
• Gurjar , M.K. , Reddy , D. S. , Bhadbhade , M. M. and Gonnade , R. G. 2004 . Diastereoselective Reformatsky reaction of methyl 4-bromocrotonate with 1,2:5,6-di-O-isopropylidene-α -D-ribo-hexofuranos-3-ulose: application to novel bicyclic nucleosides . Tetrahedron , 60 : 10269 – 10275 .
   Web of Science ®Google Scholar
• Kifli , N. , Htar , T. T. , De Clercq , E. , Balzarini , J. and Simons , C. 2004 . Novel bicyclic sugar modified nucleosides: synthesis, conformational analysis and antiviral evaluation . Bioorg. Med. Chem. , 12 : 3247 – 3257 .
   PubMed Web of Science ®Google Scholar
• Ravn , J. , Freitag , M. and Nielsen , P. 2003 . Bicyclic nucleosides; stereoselective dihydroxylation and 2′-deoxygenation . Org. Biomol. Chem. , 1 : 811 – 816 .
   PubMed Web of Science ®Google Scholar
• Christensen , N. , Andersen , A.K.L. , Schultz , T. R. and Nielsen , P. 2003 . Synthesis of hydroxymethyl branched [3.2.0]bicyclic nucleosides using a regioselective oxetane ring-formation . Org. Biomol. Chem. , 1 : 3738 – 3748 .
   PubMed Web of Science ®Google Scholar
• Albæk , N. , Ravn , J. , Freitag , M. , Thomasen , H. , Christensen , N. K. , Petersen , M. and Nielsen , P. 2003 . Bi- and tricyclic nucleoside derivatives restricted in S-type conformations and obtained by RCM-reactions . Nucleosides, Nucleotides Nucleic Acids , 22 : 723 – 725 .
   PubMed Web of Science ®Google Scholar
• Thomasen . 2002 . 1888 – 1889 .
   Google Scholar
• Mereyala , H.B. and Pola , P. 2002 . Synthesis of 1-(3′,6′-anhydro-2′-deoxy-β -D-glucofuranosyl)-thymine . Syn. Commun. , 32 : 2453 – 2458 .
   Web of Science ®Google Scholar
• Ravn , J. and Nielsen , P. 2001 . Synthesis of bicyclic nucleosides by ring-closing metathesis . J. Chem. Soc., Perkin Trans , 1 : 985 – 993 .
   Google Scholar
• Lescop , C. , Nguyen-Kim. , P-P. and Huet , F. 2000 . Stereoselective synthesis of a [3.3.0]-fused γ -butyrolactone. Application in the preparation of bicyclic nucleosides . Tetrahedron Lett. , 41 : 3057 – 3060 .
   Web of Science ®Google Scholar
• Zhang , D. and Miller , M.J. 1999 . Polyoxins and nikkomycins: Progress in synthetic and biological studies . Curr. Pharm. Design , 5 : 73 – 99 . For reviews on complex peptidyl nucleoside antibiotics, see
   PubMed Web of Science ®Google Scholar
• Knapp , S. 1995 . Chem. Rev. Synthesis of complex nucleoside antibiotics . Chem. Rev. , 95 : 1859 – 1876 .
   Web of Science ®Google Scholar
• Isono, Current , K. 1991 . progress on nucleoside antibiotics . Pharmacol. Ther. , 52 : 269 – 286 .
   PubMed Web of Science ®Google Scholar
• 1988 . Garner, Synthetic, P. approaches to complex nucleoside antibiotics. In Studies in Natural Products Chemistry . Atta-ur-Rahman, Ed.; Elsevier: Amsterdam , 1 : 397 – 435 . Stereoselective synthesis (Part A)
   Google Scholar
• Isono , K. 1988 . J. Antibiot. , 41 : 1711 – 1739 .
   PubMed Web of Science ®Google Scholar
• Stauffer , C.S. , Bhaket , P. , Fothergill , A.W. , Rinaldi , M.G. and Datta. , A. 2007 . Total synthesis and antifungal activity of a carbohydrate ring-expanded pyranosyl nucleoside analog of nikkomycin B . J. Org. Chem. , 72 : 9991 – 9997 . For our recent studies on peptidyl nucleosides, see
   PubMed Web of Science ®Google Scholar
• Khalaf , J.K. and Datta , A. 2005 . Stereoselective route to the ezoaminuroic acid core of the ezomycins . J. Org. Chem. , 70 : 6937 – 6940 .
   PubMed Web of Science ®Google Scholar
• Bhaket , P. , Stauffer , C. S. and Datta , A. 2004 . Complex Peptidyl nucleoside antibiotics: Efficient syntheses of the glycosyl nucleoside amino acid cores . J. Org. Chem. , 69 : 8594 – 8601 .
   PubMed Web of Science ®Google Scholar
• Bhaket , P. , Morris , K. , Stauffer , C.S. and Datta , A. 2005 . Total synthesis of cytotoxic anhydrophytosphingosine pachastrissamine (jaspine B) . Org. Lett. , 7 : 875 – 876 .
   PubMed Web of Science ®Google Scholar
• Vorbrüggen , H. and Ruh-Pohlenz , C. 2000 . Synthesis of nucleosides . Org. React. , 55 : 1 – 630 . For a review, see; and references therein
   Web of Science ®Google Scholar