Polymer-Assisted Structural Modification on Nucleosides and Nucleotides

REFERENCES

• Girardet , J.L. and Lang , S. A. 2007 . “ Recent developments in the chemistry of nucleosides, ed ” . In Progress in Heterocyclic Chemistry, Vol. 18 , Edited by: Gribble , G. W. and Joule , J. A. 27 – 54 . Elsevier Science .
   Google Scholar
• Ding , Y. , Habib , Q. , Shaw , S. Z. , Li , D. Y. , Abt , J. W. , Hong , Z. and An , H. 2003 . Synthesis of new 3′-, 5-, and N4-modified 2′-O-methylcytidine libraries on solid support . J. Comb. Chem , 5 : 851 – 859 .
   PubMed Web of Science ®Google Scholar
• Oliviero , G. , D’Errico , S. , Borbone , N. , Amato , J. , Piccialli , V. , Varra , M. , Piccialli , G. and Mayol , L. 2010 . A solid-phase approach to the synthesis of N-1-alkyl analogues of cyclic inosine-diphosphate-ribose (cIDPR) . Tetrahedron , 66 : 1931 – 1936 .
   Web of Science ®Google Scholar
• Oliviero , G. , D’Errico , S. , Borbone , N. , Amato , J. , Piccialli , V. , Varra , M. , Piccialli , G. and Mayol , L. 2008 . Synthesis of N-1-alkyl analogues of cyclic inosine diphosphate ribose (cIDPR) by a new solid phase approach . Nucleic Acids Symp. Ser , 52 : 573 – 574 .
   Google Scholar
• Ramasamy , K. S. , Amador , R. B. , Habib , Q. , Rong , F. , Han , X. , Li , D. Y. , Huang , J. , Hong , Z. and An , H. 2005 . Solid-phase parallel synthesis of 4-β-d-ribofuranosylpyrazolo[4,3-d]pyrimidine nucleosides . Nucleosides Nucleotides Nucleic Acids , 24 : 1947 – 1970 .
   PubMed Web of Science ®Google Scholar
• Varaprasad , C. V.N.S. , Habib , Q. , An , H. and Hong , Z. 2006 . Solid-Phase synthesis of 5′-deoxy-5′-amino-clitocine analogues . Nucleosides Nucleotides Nucleic Acids , 25 : 61 – 72 .
   PubMed Web of Science ®Google Scholar
• Oliviero , G. , Amato , J. , Borbone , N. , D’Errico , S. , Piccialli , G. and Mayol , L. 2007 . Synthesis of N-1 and ribose modified inosine analogues on solid support . Tetrahedron Lett , 48 : 397 – 400 .
   Web of Science ®Google Scholar
• Oliviero , G. , Amato , J. , Borbone , N. , D’Errico , S. , Piccialli , G. , Bucci , E. , Piccialli , V. and Mayol , L. 2008 . Synthesis of 4-N-alkyl and ribose-modified AICAR analogues on solid support . Tetrahedron , 64 : 6475 – 6481 .
   Web of Science ®Google Scholar
• Oliviero , G. , Amato , J. , D’Errico , S. , Borbone , N. , Piccialli , G. and Mayol , L. 2007 . Solid phase synthesis of nucleobase and ribose modified inosine nucleoside analogues . Nucleosides Nucleotides Nucleic Acids , 26 : 1649 – 1652 .
   PubMed Web of Science ®Google Scholar
• Varaprasad , C. V. , Habib , Q. , Li , D. Y. , Huang , J. , Abt , J. W. , Rong , F. , Hong , Z. and An , H. 2003 . Synthesis of novel exocyclic amino nucleosides by parallel solid-phase combinatorial strategy . Tetrahedron , 59 : 2297 – 2307 .
   Web of Science ®Google Scholar
• Yadav , V. , Chu , C. K. , Rais , R. H. , Safarjalani , O. N. A. , Guarcello , V. , Naguib , F. N. M. and el Kouni , M. H. 2004 . Synthesis, biological activity and molecular modeling of 6-benzylthioinosine analogues as subversive substrates of Toxoplasma gondii adenosine kinase . J. Med. Chem , 47 : 1987 – 1996 .
   PubMed Web of Science ®Google Scholar
• Gunic , E. , Amador , R. , Rong , F. , Abt , J. W. , An , H. , Hong , Z. and Girardet , J.-L. 2004 . Synthesis of nucleoside libraries on solid support. I. N 2, N 6-disubstituted diaminopurine nucleosides . Nucleosides Nucleotides Nucleic Acids , 23 : 495 – 499 .
   PubMed Web of Science ®Google Scholar
• Sun , D. and Lee , R. E. 2007 . Solid-Phase synthesis of a thymidinyl dipeptide urea library . J. Comb. Chem , 9 : 370 – 385 .
   PubMed Web of Science ®Google Scholar
• Sun , D. and Lee , R. E. 2005 . Solid-phase synthesis development of a thymidinyl and 2′-deoxyuridinyl Ugi library for anti-bacterial agent screening . Tetrahedron Lett , 46 : 8497 – 8501 .
   Web of Science ®Google Scholar
• Sun , D. , Jones , V. , Carson , E. I. , Lee , R. E. B. , Scherman , M. S. , McNeil , M. R. and Lee , R. E. 2007 . Solid-phase synthesis and biological evaluation of a uridinyl branched peptide urea library . Bioorg. Med. Chem. Lett , 17 : 6899 – 6904 .
   PubMed Web of Science ®Google Scholar
• Sun , D. and Lee , R. E. 2008 . “ High-throughput solid-phase synthesis of nucleoside-based libraries in the search for new antibiotics ” . In High-Throughput Lead Optimization in Drug Discovery , Edited by: Kshirsagar , T. 215 – 238 . CRC Press .
   Google Scholar
• Zhao , P. , Jin , H.-W. , Yang , Z.-J. , Zhang , L.-R. and Zhang , L.-H. 2008 . Solid-phase synthesis and evaluation of TAR RNA targeted β-carboline–nucleoside conjugates . Org. Biomol. Chem , 6 : 3741 – 3750 .
   PubMed Web of Science ®Google Scholar
• Rodenko , B. , Wanner , M. J. and Koomen , G.-J. 2002 . Solid phase synthesis of C2, N 6-disubstituted adenosine analogues . J. Chem. Soc. Perkin Trans , 1 : 1247 – 1252 .
   Google Scholar
• Crimmins , M. T. and Zuercher , W. J. 2000 . Solid-Phase synthesis of carbocyclic nucleosides . Org. Lett , 2 : 1065 – 1067 .
   PubMed Web of Science ®Google Scholar
• Choo , H. , Chong , Y. and Chu , C. K. 2001 . Solid phase synthesis of carbocyclic L-2′-deoxynucleosides . Org. Lett , 3 : 1471 – 1473 .
   PubMed Web of Science ®Google Scholar
• De Champdore , M. , De Napoli , L. , Di Fabio , G. , Messere , A. , Montesarchio , D. and Piccialli , G. 2001 . New nucleoside based solid supports. Synthesis of 5′, 3′-derivatized thymidine analogues . Chem. Commun , : 2598 – 2599 .
   Web of Science ®Google Scholar
• De Champdore , M. , De Napoli , L. , Di Fabio , G. , Messere , A. , Montesarchio , D. and Piccialli , G. 2003 . New solid supports linking nucleoside scaffolds . Nucleoside Nucleotide Nucleic Acids , 22 : 695 – 697 .
   PubMed Web of Science ®Google Scholar
• De Napoli , L. , Di Fabio , G. , D’Onofrio , J. and Montesarchio , D. 2004 . New nucleoside-based polymeric supports for the solid phase synthesis of ribose-modified nucleoside analogues . Synlett , : 1975 – 1979 .
   Web of Science ®Google Scholar
• Bozzoli , A. , Kazmierski , W. , Kennedy , G. , Pasquarello , A. and Pecunioso , A. 2000 . A solid-phase approach to analogues of the antibiotic mureidomycin . Bioorg. Med. Chem. Lett , 10 : 2759 – 2763 .
   PubMed Web of Science ®Google Scholar
• Epple , R. , Kudirka , R. and Greenberg , W. A. 2003 . Solid-Phase synthesis of nucleoside analogues . J. Comb. Chem , 5 : 292 – 310 .
   PubMed Web of Science ®Google Scholar
• Aucagne , V. , Berteina-Raboin , S. , Guenot , P. and Agrofoglio , L. A. 2004 . Palladium-Catalyzed synthesis of uridines on polystyrene-based solid supports . J. Comb. Chem , 6 : 717 – 723 .
   PubMed Web of Science ®Google Scholar
• Dong , G. M. , Zhang , L. R. and Zhang , L. H. 2003 . Solid-phase synthesis of dipeptide-conjugated nucleosides and their interaction with RNA . Helv. Chim. Acta , 86 : 3516 – 3524 .
   Web of Science ®Google Scholar
• Filippov , D. V. , Van den Elst , H. , Tromp , C. M. , van der Marel , G. A. , van Boeckel , C. A. A. , Overkleeft , H. S. and van Boom , J. H. 2004 . Parallel solid phase synthesis of tricomponent bisubstrate analogues as potential fucosyltransferase inhibitors . Synlett , : 773 – 778 .
   Web of Science ®Google Scholar
• Heidler , P. , Zohrabi-Kalantari , V. , Kaiser , M. , Brun , R. , Emmrich , T. and Link , A. 2009 . Inhibitors of adenosine consuming parasites through polymer-assisted solution phase synthesis of lipophilic 5′-amido-5′-deoxyadenosine derivatives . Bioorg. Med. Chem , 17 : 1428 – 1436 .
   PubMed Web of Science ®Google Scholar
• Zohrabi-Kalantari , V. , Heidler , P. , Kaiser , M. , Brun , R. , Kamper , C. and Link , A. 2010 . Inhibitors of adenosine consuming parasites through polymer-assisted N-acylation of N 6-substituted 5′-amino-5′-deoxyadenosines . Mol. Divers , 14 : 307 – 320 .
   PubMed Web of Science ®Google Scholar
• Golisade , A. , Bressi , J. C. , Van Calenbergh , S. , Gelb , M. H. and Link , A. 2000 . Polymer-Assisted solution-phase synthesis of 2′-amido-2′-deoxyadenosine derivatives targeted at the NAD+-binding sites of parasite enzymes . J. Comb. Chem , 2 : 537 – 544 .
   PubMed Web of Science ®Google Scholar
• Herforth , C. , Wiesner , J. , Franke , S. , Golisade , A. , Jomaa , H. and Link , A. 2002 . Antimalarial activity of N 6-substituted adenosine derivatives (Part 2) . J. Comb. Chem , 4 : 302 – 314 .
   PubMed Web of Science ®Google Scholar
• Link , A. , van Calenbergh , S. and Herdewijn , P. 1998 . Practical method for the parallel synthesis of 2′-amido-2′-deoxyadenosines . Tetrahedron Lett , 39 : 5175 – 5176 .
   Web of Science ®Google Scholar
• Bressi , J. C. , Choe , J. , Hough , M. T. , Buckner , F. S. , Van Voorhis , W. C. , Verlinde , C. L. M. J. , Hol , W. G. J. and Gelb , M. H. 2000 . Adenosine analogues as inhibitors of trypanosoma brucei phosphoglycerate kinase: Elucidation of a novel binding mode for a 2-amino-N 6-aubstituted adenosine . J. Med. Chem , 43 : 4135 – 4150 .
   PubMed Web of Science ®Google Scholar
• Van Calenbergh , S. , Link , A. , Fujikawa , S. , de Ligt , R. A. F. , Vanheusden , V. , Golisade , A. , Blaton , N. M. , Rozenski , J. , IJzerman , A. P. and Herdewijn , P. 2002 . 5′-Deoxy Congeners of 9-(3-Amido-3-deoxy-β-D-xylofuranosyl)-N 6-cyclopentyladenine: New adenosine A1 receptor antagonists and inverse agonists . J. Med. Chem , 45 : 1845 – 1852 .
   PubMed Web of Science ®Google Scholar
• Herforth , C. , Wiesner , J. , Heidler , P. , Sanderbrand , S. , Van Calenbergh , S. , Jomaa , H. and Link , A. 2004 . Antimalarial activity of N 6-substituted adenosine derivatives . Part 3. Bioorg. Med. Chem , 12 : 755 – 762 .
   PubMed Web of Science ®Google Scholar
• Golisade , A. , Wiesner , J. , Herforth , C. , Jomaa , H. and Link , A. 2002 . Anti-Malarial activity of N 6-Substituted adenosine derivatives . Part I. Bioorg. Med. Chem , 10 : 769 – 777 .
   PubMed Web of Science ®Google Scholar
• Golisade , A. , Van Calenbergh , S. and Link , A. 2000 . 2′-Amino-2′-deoxy-N 6-(1-naphthylmethyl)adenosine as novel scaffold for a polymer-assisted amidation protocol . Tetrahedron , 56 : 3167 – 3172 .
   Web of Science ®Google Scholar
• Rodenko , B. , Detz , R. J. , Pinas , V. A. , Lambertucci , C. , Brun , R. , Wanner , M. J. and Koomen , G.-J. 2006 . Solid phase synthesis and antiprotozoal evaluation of di- and trisubstituted 5′-carboxamidoadenosine analogues . Bioorg. Med. Chem , 14 : 1618 – 1629 .
   PubMed Web of Science ®Google Scholar
• Khan , S. I. and Grinstaff , M. W. 1998 . A facile and convenient solid-phase procedure for synthesizing nucleoside hydroxamic acids . Tetrahedron Lett , 39 : 8031 – 8034 .
   Web of Science ®Google Scholar
• Wang , S. , Lee , W. S. , Ha , H.-H. and Chang , Y.-T. 2011 . Combinatorial synthesis of galactosyl-1, 3, 5-triazines as novel nucleoside analogues . Org. Biomol. Chem , 9 : 6924 – 6926 .
   PubMed Web of Science ®Google Scholar
• Bae , S. and Lakshman , M. K. 2008 . A novel polymer supported approach to nucleoside modification . J. Org. Chem , 73 : 3707 – 3713 .
   PubMed Web of Science ®Google Scholar
• Tripathi , S. , Misraa , K. and Sanghvi , Y. S. 2005 . Polymer supported carbodiimide strategy for the synthesis of N-acylated derivatives of deoxy- and ribo purinenucleosides using active esters . Bioorg. Med. Chem. Lett , 15 : 5045 – 5048 .
   PubMed Web of Science ®Google Scholar
• Garg , N. K. , Woodroofe , C. C. , Lacenere , C. J. , Quake , S. R. and Stoltz , B. M. 2005 . A ligand-free solid-supported system for Sonogashira couplings: applications in nucleoside chemistry . Chem. Commun , : 4551 – 4553 .
   PubMed Web of Science ®Google Scholar