Progress in 7-deazapurine - Pyrrolo[2,3-d]pyrimidine - Ribonucleoside synthesis

Current Topics in Medicinal Chemistry

Volumn 6, Issue 9, 2006, Pages 867-892

  Seela, Frank ^a,b   Peng, Xiaohua ^a,b  

^a UNIVERSITY OF OSNABRÜCK   (Germany)

^b UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

7 deazapurine; C nucleoside; Glycosylation; L nucleoside; Natural occurrence; Pharmacological properties; Pyrrolo 2,3 d pyrimidine; Ribonucleoside

Indexed keywords

5' DEOXY 7 IODOTUBERCIDIN; 7 DEAZAGUANOSINE; 7 DEAZAPURINE DERIVATIVE; AB 116; ALKYNYL GROUP; AMIDE; ARCHAEOSINE; BROMINE DERIVATIVE; CADEGUOMYCIN; CLEVUDINE; DAPIRAMYCIN; ELVUCITABINE; GUANOSINE DERIVATIVE; KANAGAWAMICIN; LAMIVUDINE; METAL; METHYL GROUP; MYCALISINE A; MYCALISINE B; NUCLEOSIDE DERIVATIVE; PYRIMIDINE DERIVATIVE; PYRROLE DERIVATIVE; QUEUOSINE; RIBONUCLEOSIDE DERIVATIVE; SANGIVAMYCIN DERIVATIVE; SCHIFF BASE; SODIUM CHLORIDE; TOYOCAMYCIN DERIVATIVE; TUBERCIDIN; TUBERCIDIN DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; DRUG SYNTHESIS; ENANTIOMER; GLYCOSYLATION; HEPATITIS B; HUMAN; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; LIQUID LIQUID EXTRACTION; NONHUMAN; REACTION ANALYSIS; REVIEW; STREPTOMYCES;

PURINES; PYRIMIDINES; PYRROLES; RIBONUCLEOSIDES;

EID: 33744490082     PISSN: 15680266     EISSN: None     Source Type: Journal    
DOI: 10.2174/156802606777303649     Document Type: Review

References (103)

1. Suhadolnik, R. J. Pyrrolopyrimidine Nucleosides. In Nucleoside Antibiotics; Wiley-Interscience, New York, 1970; pp. 298-353.
2. Suhadolnik, R. J. Pyrrolopyrimidine Nucleosides Analogs. In Nucleosides as Biological Probes; Wiley-Interscience, New York, 1979; pp. 158-169.
3. Nakamura, G. Studies on Antibiotic Actinomycetes. II. On Streptomyces Producing a New Antibiotic Tubercidin. J. Antibiot. 1961, 14A, 90-93.
4. Nishimura, H.; Katagiri, K.; Sato, K.; Mayama, M.; Shimaoka, N. Toyocamycin, a New Anti-candida Antibiotics. J. Antibiot. 1956, 9A, 60-62.
5. Ohkuma, K. Chemical Structure of Toyocamycin. J. Antibiot. 1961, 14A, 343-352.
6. Kazlauskas, R.; Murphy, P. T.; Wells, R. J.; Baird-Lambert, J. A.; Jamieson, D. D. Halogenated Pyrrolo[2,3-d]pyrimidine Nucleosiedes from Marine Organisms. Aust. J. Chem. 1983, 36, 165-170.
7. Kasai, H.; Ohashi, Z.; Harada, F.; Nishimura, S.; Oppenheimer, N. J.; Crain, P. F.; Liehr, J. G.; von Minden, D. L.; McCloskey, J. A. Structure of the Modified Nucleoside Q Isolated from Escherichia coli Transfer Ribonucleic Acid. 7-(4,5-cis-Dihydroxy-1-cyclopenten-3-ylaminomethyl)-7-deazaguanosine. Biochemistry 1975, 14, 4198-4208.
8. Seela, F.; Hasselmann, D. Synthese von 7-Desazainosin dutch Phasentransferglycosidierung. Chem. Ber. 1980, 113, 3389-3393.
9. Seela, F.; Hasselmann, D. Synthese von 2-Amino-3,7-dihydro-7-(β-D-ribofuranosyl)-4H-pyrrolo [2,3-d]pyrimidin-4-on - 7-Desazaguanosin-der Stammverbindung des Nucleosids Q. Chem. Ber. 1981, 114, 3395-3402.
10. Kato, Y.; Fusetani, N.; Matsunaga, S.; Hashimoto, K. Bioactive Marine Metabolites. IX. Mycalisine-A and Mycalisine-B, Novel Nucleosides Which Inhibit Cell-division of Fertilized Starfish Eggs, from the Marine Sponge Mycale sp. Tetrahedron Lett. 1985, 26, 3483-3486.
11. Meade, E. A.; Krawczyk, S. H.; Townsend, L. B. A Total Synthesis of the Naturally Occurring Pyrrolo[2,3-d]pyrimidine Nucleoside, Mycalisine A. Tetrahedron Lett. 1988, 29, 4073-4076.
12. Tanaka, N.; Wu, R. T.; Okabe, T.; Yamashita, H.; Shimazu, A.; Nishimura, T. Cadeguomycin, a Novel Nucleoside Analog Antibiotic. I. the Producing Organism, Production and Isolation of Cadeguomycin. J. Antibiot. 1982, 35, 272-278.
13. Naruto, S.; Uno, H.; Tanaka, A.; Kotani, H.; Takase, Y. Kanagawamicin - a New Aminonucleoside Analog Antibiotic from Actinoplanes Kanagawaensis. Heterocycles 1993, 20, 27-32.
14. Shomura, T.; Nishizawa, N.; Iwata, N.; Yoshida, J.; Ito, M.; Amano, S.; Koyama, M.; Kojima, M.; Inouye, S. Studies on a New Nucleoside Antibiotic, Dapiramicin, I. Producing Organism, Assay Method and Fermentation. J. Antibiot. 1983, 36, 1300-1304.
15. Nishizawa, N.; Kondo, Y.; Koyama, M.; Omoto, S.; Iwata, M.; Tsuruoka, T.; Inouye, S. Studies on a New Nucleoside Antibiotic, Dapiramicin, II. Isolation, Physicochemical and Biological Characterization. J. Antibiot. 1984, 37, 1-5.
16. Seto, H.; Otake, N.; Koyama, M.; Ogino, H.; Kodama, Y.; Nishizawa, N.; Tsuruoka, T.; Inouye, S. The Structure of a Novel Nucleoside Antibiotic, Dapiramicin-A. Tetrahedron Lett. 1983, 24, 495-498.
17. Martin, J. C. Nucleotide Analogues as Antiviral Agents. American Chemical Society, Washington, 1989.
18. Ritch, P. S.; Glazer, R. I. Pyrrolo[2,3-d]pyrimidine nucleosides. In Developments in Cancer Chemotherapy; Glazer, R. I.; Ed.; CRC Press, Boca Raton, Florida 1984; pp. 1-33.
19. Henderson, J. F.; Paterson, A. R.; Caldwell, I. C.; Paul, B.; Chan, M. C.; Lau, K. F. Inhibitors of Nucleoside and Nucleotide Metabolism. Cancer Chemother. Rep. 1972, 3, 71-85.
20. Mizusawa, S.; Nishimura, S.; Seela, F. Improvement of the Dideoxy Chain Termination Method of DNA Sequencing by Use of Deoxy-7-deazaguanosine Triphosphate in Place of dGTP. Nucleic Acids Res. 1986, 14, 1319-1324.
21. Seela, F.; Winkeler, H.-D.; Ott, J.; Tran-Thi, Q.-H.; Hasselmann, D.; Franzen, D.; Bussmann, W. Synthesis of Pyrrolo[2,3-d] pyrimidin Nucleosides by Phasetransfer Glycosylation and their Function in Polynucleotides. In Nucleosides, Nucleotides and Their Biological Application; Rideout, J. L.; Henry, D. W.; Beacham III, L. M. Eds.; Academic Press, New York, 1983; pp. 181-208.
22. Revankar, G. R.; Robins, R. K. Pyrrolo[2,3-d]pyrimidine (7-Deazapurine) Nucleosides. In Chemistry of Nucleosides and Nucleotides; Townsend, L.B.; Ed.; Plenum Press, New York, 1991; pp 200-247.
23. Isono, K. Current Progress on Nucleoside Antibiotics. Pharmacol. Ther. 1991, 52, 269-286.
24. Seela, F.; Peng, X. Base-modified Oligodeoxyribonucleotides: Using pyrrolo[2,3-d]pyrimidines to Replace Purines. In Current Protocols in Nucleic Acid Chemistry; Beaucage, S. L.; Bergstrom, D. E.; Glick, G. D.; Jones, R. A.; Eds.; John Wiley & Sons, 2005; pp. 4.25.1-4.25.24.
25. Seela, F.; Peng, X. Synthesis and Properties of 7-Substituted 7-Deazapurine (pyrrolo[2,3-d]pyrimidne) 2′-Deoxyribonucleosides. In Current Protocols in Nucleic Acid Chemistry; Beaucage, S. L.; Bergstrom, D. E.; Glick, G. D.; Jones, R. A.; Eds.; John Wiley & Sons, 2005; pp 1.10.1-1.10.20.
26. Winkeler, H.-D.; Seela, F. 2-Amino-7-(2′-deoxy-β-D-erythropentofuranosyl)-3, 7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one, a New Isostere of 2′-Deoxyguanosine. J. Org. Chem. 1983, 48, 3119-3122.
27. Seela, F.; Westermann, B.; Bindig, U. Liquid-liquid and Solid-liquid Phase-transfer Glycosylation of Pyrrolo[2,3-d]pyrimidines: Stereospecific Synthesis of 2-Deoxy-β-D-ribofuranosides Related to 2′-Deoxy-7-carbaguanosine. J. Chem. Soc., Perkin Trans I 1988, 697-702.
28. Kazimierczuk, Z.; Cottam, H. B.; Revankar, G. R.; Robins, R. K. Synthesis of 2′-Deoxytubercidin, 2′-Deoxyadenosine, and Related 2′-Deoxynucleosides via a Novel Direct Stereospecific Sodium Salt Glycosylation Procedure. J. Am. Chem. Soc. 1984, 106, 6379-6382.
29. Buhr, C. A.; Wagner, R. W.; Grant, D.; Froehler, B. C. Oligodeoxynucleotides Containing C-7 Propyne Analogs of 7-Deaza-2′-deoxyguanosine and 7-Deaza-2′-deoxyadenosine. Nucleic Acid Res. 1996, 24, 2974-2980.
30. Ramasamy, K.; Robins, R. K.; Revankar, G. R. Total and Stereospecific Synthesis of 2′-Deoxycadeguomycin. J. Chem. Soc., Chem. Commun. 1989, 560-562.
31. Kazimierczuk, Z.; Revankar, G. R.; Robins, R. K. Total Synthesis of Certain 2-, 6-mono and 2,6-Disubstituted-Tubercidin Derivatives. Synthesis of Tubercidin via the Sodium Salt Glycosylation Procedure. Nucleic Acids Res. 1984, 12, 1179-1192.
32. Cottam, H. B.; Kazimierczuk, Z.; Geary, S.; McKernan, P. A.; Revankar, G. R.; Robins, R. K. Synthesis and Biological Activity of Certain 6-Substituted and 2,6-Disubstituted 2′-Deoxytubercidins Prepared via the Stereospecific Sodium Salt Glycosylation Procedure. J. Med. Chem. 1985, 28, 1461-1467.
33. Ramasamy, K.; Imamura, N.; Robins, R. K.; Revankar, G. R. A Facile and Improved Synthesis of Tubercidin and Certain Related Pyrrolo[2,3-d]pyrimidine Nucleosides by the Stereospecific Sodium Salt Glycosylation Procedure. J. Heterocyclic Chem. 1988, 25, 1893-1898.
34. 15N-NMR Spectra. Helv. Chim. Acta 1988, 71, 1573-1585.
35. Seela, F.; Soulimane, T.; Mersmann, K.; Jürgens, T. 2,4-Disubstituted Pyrrolo[2,3-d]pyrimidine α-D- and β-D-Ribofuranosides Related to 7-Deazaguanosine. Helv. Chim. Acta 1990, 73, 1879-1887.
36. Taylor, E. C.; Hendess, R. W. Synthesis of Pyrrolo[2,3-d]pyrimidines. The Aglycone of Toyocamycin. J. Am. Chem. Soc. 1965, 87, 1995-2003.
37. Tolman, R. L.; Tolman, G. L.; Robins, R. K.; Townsend, L. B. Pyrrolopyrimidine Nucleosides. VI. Synthesis of 1,3 and 7-β-D-Ribofuranosylpyrrolo[2,3-d]pyrimidines via Silylated Intermediates (1a). J. Heterocyclic. Chem. 1970, 7, 799-806.
38. Townsend, L. B.; Tolman, R. L.; Robins, R. K.; Milne, G. H. The synthesis of 2-Amino-7-(β-D-ribofuranosyl)pyrrolo[2,3-d]-pyrimidin-4-one (7-Deazaguanosine), a Nucleoside Q and Q* Analog (1). J. Heterocyclic. Chem. 1976, 13, 1363-1364.
39. Lüpke, U.; Seela, F. Ribosidierung von 7H-Pyrrolo[2,3-d]pyrimidin-4(3B)-on an N-3. Chem. Ber. 1979, 112, 3526-3529.
40. Lüpke, U.; Seela, F. Bevorzugte O-Glycosidbildung bei der Ribosidierung von 5-Methyl-2-methylthio-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-on. Chem. Ber. 1979, 112, 799-806.
41. 1. Synthesis of 4-Hydroxy-7-β-D-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidine, a Tubercidin Analog. J. Org. Chem. 1963, 28, 3331-3336.
42. Tolman, R. L.; Robins, R. K.; Townsend, L. B. Pyrrolopyrimidine Nucleosides. (II). The Total Synthesis of 7-β-D-Ribofuranosyl-pyrrolo[2,3-d]pyrimidines Related to Toyocamycin (1, 1a). J. Heterocyclic. Chem. 1967, 4, 230-238.
43. Tolman, R. L.; Robins, R. K.; Townsend, L. B. Pyrrolo[2,3-d]pyrimidine Nucleoside Antibiotics. Total Synthesis and Structure of Toyocamycin, Unamycin B, Vengicide, Antibiotic E-212, and Sangivamycin (BA-90912). J. Am. Chem. Soc. 1968, 90, 524-526.
44. Hashizume, T.; Iwamura, H. A New Catalyst for the Synthesis of Nucleosides. Tetrahedron Lett. 1965, 6, 3095-3102.
45. Tolman, R. L.; Robins, R. K.; Townsend, L. B. Pyrrolopyrimidine Nucleosides. III. The Total Synthesis of Toyocamycin, Sangivamycin, Tubercidin, and Related Derivatives. J. Am. Chem. Soc. 1969, 91, 2102-2108.
46. Iwamura, H.; Hashizum, T. Synthesis in Nucleoside Antibiotics. Part III. Synthesis of 4-Amino-5-cyano-6-methylmercaptopyrrolo [2,3-d]pyrimidine-7-β-D-ribosides (Toyocamycin Analogs). Agric. Biol. Chem. 1968, 32, 1010-1015.
47. Ektova, L. V.; Tolkachev, V. N.; Kornveits, M. Z.; Preobrazhenskaya, M. N. New Total Synthesis of Tubercidin Antibiotic (7-Deazadenosine). Bioorg. Khim. 1978, 4, 1250-1255.
48. Davoll, J.; Lowy, B. A. A New Synthesis of Purine Nucleosides. The Synthesis of Adenosine, Guanosine and 2,6-Diamino-9-β-D-ribofuranosylpurine. J. Am. Chem. Soc. 1951, 73, 1650-1655.
49. Taylor, E. C., Hendess, R. W. Synthesis of 4-Amino-5-cyanopyrrolo[2,3-d]pyrimidine, the Aglycone of Toyocamycin. J. Am. Chem. Soc. 1964, 86, 951-952.
50. Bobek, M.; Whistler, R. L.; Bloch, A. Synthesis and Biological Activity of 4′-Thio Analogs of the Antibiotic Toyocamycin. J. Med. Chem. 1972, 15, 168-171.
51. Birkofer, L.; Ritter, A.; Kühlthau, H. P. Harnsaure-3-ribofuranosid und Harnsaure-3-glucopyranosid-N-glykoside durch Siliciumorganische Synthese. Angew. Chem. 1963, 4, 209-210.
52. Birkofer, L.; Kühlthau, H. P.; Ritter, A. Alkylierungen und Glykosidierungen über Silyl-derivate. Chem. Ber. 1964, 97, 934-945.
53. Nishimura, T.; Shimizu, B.; Iwai, I. A New Synthetic Method of Nucleosides. Chem. Pharm. Bull. (Tokyo) 1963, 11, 1470-1472.
54. Nishimura, T.; Iwai, I. Studies on Synthetic Nucleosides. (II). Novel Synthesis of Pyrimidine Glucosides. Chem. Pharm. Bull. 1964, 12, 357-361.
55. Wittenburg, E. A New Synthesis of Nucleosides. Z. Chem. 1964, 4, 303-304.
56. Vorbrüggen, H.; Ruh-Pohlenz, C. Synthesis of Nucleosides. Org. React. 2000, 55, 1-630.
57. Colvin, E. W. Silicon in Organic Synthesis; Butterworths: London, 1981; P 4.
58. Lukevics, E.; Zablocka, A. Nucleoside Synthesis Organosilicon Methods; Horwood, E.; Ed.; New York, 1991.
59. Vorbrüggen, H. Adventures in Silicon-Organic Chemistry. Acc. Chem. Res. 1995, 28, 509-520.
60. Wittenburg, E. Nucleoside und Verwandte Verbindungen. III. Synthese von Thymim-nucleosiden über Silyl-pyrimidin-Verbindungen. Chem. Ber. 1968, 101, 1095-1114.
61. Barker, R.; Fletcher, Jr., H. G. 2,3,5-Tri-O-benzoyl-D-ribosyl and -L-arabinosyl Bromides. J. Ong. Chem. 1961, 26, 4605-4609.
62. Seela, F.; Ming, X. 2006, (unpublished data).
63. Sharma, M.; Bloch, A.; Bobek, M. A Pratical Synthesis of the Antibiotic Toyocamycin. Nucleosides Nucleotides 1993, 12, 643-648.
64. Recondo, E. F.; Rinderknecht, H. Eine Neue, Einfache Synthese des 1-O-Acetyl-2,3,5-tri-O-Benzoyl-β-D-Ribofuranosides. Helv. Chim. Acta 1959, 42, 1171-1173.
65. Porcari, A. R.; Townsend, L. B. Total Synthesis of the Naturally Occurring Antibiotic Toyocamycin Using New and Improved Synthetic Procedures. Nucleoside Nucleotides 1999, 18, 153-159.
66. Seela, F.; Peng, X. 7-Functionalized 7-Deazapurine Ribonucleosides Related to 2-Aminoadenosine, Guanosine, and Xanthosine: Glycosylation of Pyrrolo[2,3-d]pyrimidines with 1-O-Acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose. J. Org. Chem. 2006, 71,81-90.
67. Seela, F.; Peng, X. Regioselective Syntheses of 7-Halogenated 7-Deazapurine Nucleosides Related to 2-Amino-7-deaza-2′-deoxyadenosine and 7-Deaza-2′-deoxyisoguanosine. Synthesis 2004, 1203-1210.
68. Seela, F.; Shaikh, K. 7-Halogenated 7-Deaza-2′-deoxyxanthine 2′-Deoxyribonucleosides. Helv. Chim. Acta 2004, 87, 1325-1332.
69. Seela, F.; Zulauf, M. Palladium-Catalyzed Cross Coupling of 7-Iodo-2′-deoxytubercidin with Terminal Alkynes. Synthesis 1996, 726-730.
70. Wang, X.; Seth, P. P.; Ranken, R.; Swayze, E. E.; Migawa, M. T. Synthesis and Biological Activity of 5-Fluorotubercidin. Nucleosides Nucleotides Nucleic Acids 2004, 23, 161-170.
71. Pudlo, J. S.; Nassiri, M. R.; Kern, E. R.; Wotring, L. L.; Drach, J. C.; Townsend, L. B. Synthesis, Antiproliferative, and Antiviral Activity of Certain 4-Substituted and 4,5-Disubstituted 7-[(1,3-Dihydroxy-2-propoxy) methyl]pyrrolo[2,3-d]pyrimidines. J. Med. Chem. 1990, 33, 1984-1992.
72. Seela, F. and Xu, K. 2006, (unpublished data).
73. Kondo, T.; Ohgi, T.; Goto, T. Synthesis of 5-Methyltubercidin and its α-Anomer via Condensation of Anion of 4-Methoxy-5-methyl-2-methylithiopyrrolo[2,3-d]pyrimidine and 2, 3, 5-tri-O-Benzyl-D-ribofuranosyl Bromide. Agric. Biol. Chem. 1977, 41, 1501-1507.
74. Ohgi, T.; Kondo, T.; Goto, T. Total Synthesis of Nucleoside Q. Tetrahedron Lett. 1977, 18, 4051-4054.
75. Wilcox, C. S.; Otoski, R. M. Stereoselective Preparations of Ribofuranosyl Chlorides and Ribofuranosyl Acetates - Solvent Effects and Stereoselectivity in the Reaction of Ribofuranosyl Acetates with Trimethylallylsilane. Tetrahedron Lett. 1986, 27, 1011-1014.
76. Cristalli, G.; Vittori, S.; Eleuteri, A.; Volpini, R.; Cola, D.; Camaioni, E.; Gariboldi, P. V.; Lupidi, G. Synthesis of 1,7-Dideazapurine Ribonucleosides and Deoxyribonucleosides. Nucleosides Nucleotides 1993, 12, 39-53.
77. Seela, F.; Lüpke, U.; Hasselmann, D. Ribosidierung von Pyrrolo[2,3-d]pyrimidinen in Gegenwart Starker Basen. Chem. Ber. 1980, 113, 2808-2813.
78. Cristalli, G.; Franchetti, P.; Grifantini, M.; Nocentini, G.; Vittori, S. 3,7-Dideazapurine Nucleosides. Synthesis and Antitumor Activity of 1-Deazatubercidin and 2-Chloro-2′-deoxy-3,7-dideazaadenosine. J. Med. Chem. 1989, 32, 1463-1466.
79. Anderson, J. D.; Bontems, R. J.; Geary, S.; Cottam, H. B.; Larson, S. B.; Matsumoto, S. S.; Smee, D. F.; Robins, R. K. Synthesis of Tubercidin, 6-Chlorotubercidin and Related Nucleosides. Nucleosides Nucleotides 1989, 8, 1201-1216.
80. Kondo, T.; Okamoto, K.; Yamamoto, M.; Goto, T. A Total Synthesis of Cadeguomycin, a Nucleoside Antibiotic Produced by Streptomyces Hygroscopicus. Tetrahedron 1986, 42, 199-205.
81. Ramasamy, K.; Joshi, R. V.; Robins, R. K.; Revankar, G. R. Total and Stereospecific Synthesis of Cadeguomycin, 2′-Deoxycadeguomycin, ara-Cadeguomycin, and Certain Related Nucleosides. J. Chem. Soc. Perkin Trans. I 1989, 2375-2384.
82. (a) Ramasamy, K.; Imamura, N.; Robins, R. K.; Revankar, G. R. A Facile Synthesis of Tubercidin and Related 7-Deazapurine Nucleosides via the Stereospecific Sodium Salt Glycosylation Procedure. Tetrahedron Lett. 1987, 28, 5107-5110.
83. (b) Revankar, G. R.; Robins, R. K. Use of the Sodium Salt Glycosylation Method in Nucleoside Synthesis. Nucleosides Nucleotides 1989, 8, 709-724.
84. Zhang, L.; Zhang, Y.; Li, X.; Zhang, L. Study on the Synthesis and PKA-I Binding Activities of 5-Alkylnyl Tubercidin Analogues. Bioorg. Med. Chem. 2002, 10, 907-912.
85. Soula, G. Tris(polyoxaalkyl)amines (Trident), a New Class of Solid-Liquid Phase-Transfer Catalysts. J. Org. Chem. 1985, 50, 3717-3721.
86. Balow, G.; Mohan, V.; Lesnik, E. A.; Johnston, J. F.; Monia, B. P.; Acevedo, O. L. Biophysical and Antisense Properties of Oligodeoxynucleotides Containing 7-Propynyl-, 7-Iodo- and 7-Cyano-7-deaza-2-amino-2′-deoxyadenosines. Nucleic Acids Res. 1998, 26, 3350-3357.
87. Zhang, Y.; Zhang, L.; Yang, Z.; Min, J.; Zhang, L.; Lu, Y.; Gong, N.; Zheng, Q. Coupling Reaction of 4-Chloro-7-H-pyrrolo[2,3-d]pyrimidine with 2,3,5-tri-O-Acetyl-β-D-ribofuranosyl Chloride. Chinese Chem. Lett. 2001, 12, 391-394.
88. Ramasamy, K.; Robins, R. K.; Revankar, G. R. Direct Synthesis of Pyrrole Nucleosides by the Stereospecific Sodium Salt Glycosylation Procedure [1]. J. Heterocyclic. Chem. 1987, 24, 863-868.
89. Girgis, N. S.; Michael, M. A; Smee; D. F.; Alaghamandan, H. A.; Robins, R. K.; Cottam, H. B. Direct C-Glycosylation of Guanine Analogues: The Synthesis and Antiviral Activity of Certain 7- and 9-Deazaguanine C-Nucleosides. J. Med. Chem. 1990, 33, 2750-2755.
90. 8-(2′-Deoxy-β-D-ribofuranoside) of 7-Deazaguanine: Synthesis and Base Pairing of Oligonucleotides with Unusually Linked Nucleobases. J. Org. Chem. 2001, 66, 3303-3312.
91. Eldrup, A. B.; Allerson, C. R.; Bennett, C. F.; Bera, S.; Bhat, B.; Bhat, N.; Bosserman, M. R.; Brooks, J.; Burlein, C.; Carroll, S. S.; Cook, P. D.; Getty, K. L.; MacCoss, M.; McMasters, D. R.; Olsen, D. B.; Prakash, T. P.; Prhavc, M.; Song, Q.; Tomassini, J. E.; Xia, J. Structure-Activity Relationship of Purine Ribonucleosides for Inhibition of Hepatitis C Virus RNA-Dependent RNA Polymerase. J. Med. Chem. 2004; 47, 2283-2295.
92. Eldrup, A. B.; Prhavc, M.; Brooks, J.; Bhat, B.; Prakash, T. P.; Song, Q.; Bera, S.; Bhat, N.; Dande, P.; Cook, P. D.; Bennet, C. F.; Carroll, S. S.; Ball, R. G.; Bosserman, M.; Burlein, C.; Colwell, L. F.; Fay, J. F.; Flores, O. A.; Getty, K.; LaFemina, R. L.; Leone, J.; MacCoss, M.; McMasters, D. R.; Tomassini, J. E.; von Langen, D.; Wolanski, B.; Olsen, D. B. Structure-Activity Relationship of Heterobase-Modified 2′-C-Methyl Ribonucleosides as Inhibitors of Hepatitis C Virus RNA Replication. J. Med. Chem. 2004, 47, 5284-5297.
93. Harry-O'kuru, R. E.; Smith, J. M.; Wolfe, M. S. A Short, Flexible Route toward 2′-C-Branched Ribonucleosides. J. Org. Chem. 1997, 62, 1754-1759.
94. Ding, Y.; An, H.; Hong, Z.; Girardet, J.-L. Synthesis of 2′-β-C-Methyl Toyocamycin and Sangivamycin Analogues as Potential HCV Inhibitors. Bioorg. Med. Chem. Lett. 2005, 15, 725-727.
95. Seela, F.; Peng, X. 2005, (unpublished data).
96. Bio, M. M.; Xu, F.; Waters, M.; Williams, J. M.; Savary, K. A.; Cowden, C. J.; Yang, C.; Buck, E.; Song, Z. J.; Tschaen, D. M.; Volante, R. P.; Reamer, R. A.; Grabowski, E. J. J. Practical Synthesis of a Potent Hepatitis C Virus RNA Replication Inhibitor. J. Org. Chem. 2004, 69, 6257-6266.
97. Gumina, G.; Chong, Y.; Choo, H.; Song, G.-Y.; Chu, C. K. L-Nucleosides: Antiviral Activity and Molecular Mechanism. Curr. Top. Med. Chem. 2002, 2, 1065-1086.
98. Bryant, M. L.; Bridges, E. G.; Placidi, L.; Faraj, A.; Loi, A. G.; Pierra, C.; Dukhan, D.; Gosselin, G.; Imbach, J. L.; Hernandez, B.; Juodawlkis, A.; Tennant, B.; Korba, B.; Cote, P.; Marion, P.; Cretton-Scott, E.; Schinazi, R. F.; Sommadossi, J. P. Antiviral L-Nucleosides Specific for Hepatitis B Virus Infection. Antimicrob. Agents Chemother. 2001, 45, 229-235.
99. Seela, F.; Lin, W.; Kazimierczuk, Z.; Rosemeyer, H.; Glacon, V.; Peng, X.; He, Y.; Ming, X.; Andrzejewska, M.; Gorska, A.; Zhang, X.; Eickmeier, H.; La Colla, P. L-Nucleosides Containing Modified Nucleobases. Nucleosides, Nucleotides Nucleic Acids 2005, 24, 859-863.
100. Wang, P. Y.; Hong, J. H.; Cooperwood, J. S.; Chu, C. K. Recent Advances in L-Nucleosides: Chemistry and Biology. Antiviral Res. 1998, 40, 19-44.
101. Gumina, G.; Song, G. Y.; Chu, C. K. L-Nucleosides as Chemotherapeutic Agents. FEMS Microbiol. Lett. 2001, 202, 9-15.
102. Wang, G.; Tam, R. C.; Gunic, E.; Du, J.; Bard, J.; Pai, B. Synthesis and Cytokine Modulation Properties of Pyrrolo[2,3-d]-4-pyrimidone Nucleosides. J. Med. Chem. 2000, 43, 2566-2574.
103. Hinshaw, B. C.; Gerster, J. F.; Robins, R. K.; Townsend, L. B. Pyrrolopyrimidine Nucleosides. V. A Study on the Relative Chemical Reactivity of the 5-Cyano Group of the Nucleoside Antibiotic Toyocamycin and Desaminotoyocamycin. The Synthesis of Analogues of Sangivamycin. J. Org. Chem. 1970, 35, 236-241.