Recent Advances in Carbocyclic Nucleosides: Synthesis and Biological Activity

Medicinal Chemistry of Nucleic Acids

Volumn , Issue , 2011, Pages 1-100

  Wang, Jianing ^a   Rawal, Ravindra K ^a   Chu, Chung K ^a  

^a UNIVERSITY OF GEORGIA   (United States)

Author keywords

Carbocyclic nucleosides; Six membered carbocyclic nucleosides; Three membered carbocyclic nucleosides

Indexed keywords

EID: 84878629779     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9781118092804.ch1     Document Type: Chapter

References (247)

1. Adams, R. L. P., Knowler, J. T., Leader, D. P. The Biochemistry of the Nucleic Acids, New York: Springer 1992.
2. De Clercq, E. (2004). Antiviral drugs in current clinical use. Journal of Clinical Virology, 30 , 115-133.
3. Galmarini, C., Mackey, J., Dumontet, C. (2002). Nucleoside analogues and nucleobases in cancer treatment. The Lancet Oncology, 3 , 415-424.
4. Stoeckler, J., Cambor, C., Parks Jr., R. (1980). Human erythrocytic purine nucleoside phosphorylase: Reaction with sugar-modified nucleoside substrates. Biochemistry, 19 , 102-107.
5. Shealy, Y., Clayton, J. (1966). 9 [β-dl-2a, 3a-dihydroxy-4β-(hydroxymethyl)-cyclopentenyl] adenine, the carbocyclic analog of adenosine. Journal of the American Chemical Society, 88 , 3885-3887.
6. Hayashi, M., Yaginuma, S., Muto, N., Tsujino, M. (1980) Structures of neplanocins, new antitumor antibiotics. Nucleic Acids Symposium Series, vol. 8, s65-67
7. Kusaka, T., Yamamoto, H., Shibata, M., Muroi, M., Kishi, T. (1968). Streptomyces citricolor nov. Sp. And a new antibiotic, aristeromycin. Journal of Antibiotics, 21 , 255-263.
8. Agrofoglio, L., Suhas, E., Farese, A., Condom, R., Challand, S., Earl, R., Guedj, R. (1994). Synthesis of carbocyclic nucleosides. Tetrahedron, 50 , 10611-10670.
9. Crimmins, M. (1998). New developments in the enantioselective synthesis of cyclopentyl carbocyclic nucleosides. Tetrahedron, 54 , 9229-9272.
10. Jeong, L., Lee, J. (2004). Recent advances in the synthesis of the carbocyclic nucleosides as potential antiviral agents. Antiviral Chemistry & Chemotherapy, 15 , 235-250.
11. Schneller, S. (2002). Carbocyclic nucleosides (carbanucleosides) as new therapeutic leads. Current Topics in Medicinal Chemistry, 2 , 1087-1092.
12. Zhu, X. (2000). The latest progress in the synthesis of carbocyclic nucleosides. Nucleosides, Nucleotides and Nucleic Acids, 19 , 651-690.
13. Marquez, V. E., Lim, M. I. (1986). Carbocyclic nucleosides. Medicinal Research Reviews, 6 , 1-40.
14. Borchardt, R., Keller, B., Patel-Thombre, U. (1984). Neplanocin A. A potent inhibitor of S -adenosylhomocysteine hydrolase and of vaccinia virus multiplication in mouse l929 cells. Journal of Biological Chemistry, 259 , 4353.
15. Borchardt, R., Wu, Y. (1976). S -aristeromycinyl-L-homocysteine, a potent inhibitor of S -adenosylmethionine-dependent transmethylations. Journal of Medicinal Chemistry, 19 , 197-198.
16. Coward, J., Slisz, E. (1973). Analogs of S -adenosylhomocysteine as potential inhibitors of biological transmethylation. Specificity of the S -adenosylhomocysteine binding site. Journal of Medicinal Chemistry, 16 , 460-463.
17. Coward, J., Sweet, W. (1972). Analogs of S -adenosylhomocysteine as potential inhibitors of biological transmethylation. Synthesis and biological activity of homocysteine derivatives bridged to adenine. Journal of Medicinal Chemistry, 15 , 381-384.
18. De Clercq, E. (1987). S -adenosylhomocysteine hydrolase inhibitors as broadspectrum antiviral agents. Biochemical Pharmacology, 36 , 2567-2575.
19. Guranowski, A., Montgomery, J., Cantoni, G., Chiang, P. (1981). Adenosine analogs as substrates and inhibitors of S -adenosylhomocysteine hydrolase. Biochemistry, 20 , 110-115.
20. Palmer, J., Abeles, R. (1979). The mechanism of action of S -adenosylhomocysteinase. Journal of Biological Chemistry, 254 , 1217.
21. Parry, R., Askonas, L. (1985). Studies of enzyme stereochemistry. Elucidation of the stereochemistry of the reaction catalyzed by S -adenosylhomocysteine hydrolase. Journal of the American Chemical Society, 107 , 1417-1418.
22. Sinhababu, A., Bartel, R., Pochopin, N., Borchardt, R. (1985). Mechanism of action of S -adenosyl-L-homocysteine hydrolase. Measurement of kinetic isotope effects using adenosine-3'-D and S -adenosyl-L-homocysteine-3'-D as substrates. Journal of the American Chemical Society, 107 , 7628-7632.
23. Abeles, R., Fish, S., Lapinskas, B. (1982). S -adenosylhomocysteinase: Mechanism of inactivation by 2'-deoxyadenosine and interaction with other nucleosides. Biochemistry, 21 , 5557-5562.
24. Matuszewska, B., Borchardt, R. (1987). The role of nicotinamide adenine dinucleotide in the inhibition of bovine liver S -adenosylhomocysteine hydrolase by neplanocin a. Journal of Biological Chemistry, 262 , 265-268.
25. Wolfson, G., Chisholm, J., Tashjian Jr, A., Fish, S., Abeles, R. (1986). Neplanocin a. Actions on S -adenosylhomocysteine hydrolase and on hormone synthesis by gh4c1 cells. Journal of Biological Chemistry, 261 , 4492-4498.
26. Jeong, L. S., Yoo, S. J., Lee, K. M., Koo, M. J., Choi, W. J., Kim, H. O., Moon, H. R., Lee, M. Y., Park, J. G., Lee, S. K., Chun, M. W. (2003). Design, synthesis, and biological evaluation of fluoroneplanocin a as the novel mechanism-based inhibitor of S -adenosylhomocysteine hydrolase. Journal of Medicinal Chemistry, 46 , 201-203.
27. Wnuk, S. F., Mao, Y., Yuan, C.-S., Borchardt, R. T., Andrei, G., Balzarini, J., De Clercq, E., Robins, M. J. (1998). Discovery of type ii (covalent) inactivation of S -adenosyl-L-homocysteine hydrolase involving its "hydrolytic activity": Synthesis and evaluation of dihalohomovinyl nucleoside analogues derived from adenosine. Journal of Medicinal Chemistry, 41 , 3078-3083.
28. Wnuk, S. F., Yuan, C.-S., Borchardt, R. T., Balzarini, J., De Clercq, E., Robins, M. J. (1994). Nucleic acid-related compounds. 84. Synthesis of 6'-(E and Z)-halohomovinyl derivatives of adenosine, inactivation of S -adenosyl-L-homocysteine hydrolase, and correlation of anticancer and antiviral potencies with enzyme inhibition. Journal of Medicinal Chemistry, 37 , 3579-3587.
29. Yang, X., Yin, D., Wnuk, S. F., Robins, M. J., Borchardt, R. T. (2000). Mechanisms of inactivation of human S -adenosylhomocysteine hydrolase by 5',5',6',6'-tetradehydro-6'-deoxy-6'-halohomoadenosines. Biochemistry, 39 , 15234-15241.
30. Yuan, C., Yeh, J., Liu, S., Borchardt, R. (1993). Mechanism of inactivation of S -adenosylhomocysteine hydrolase by (Z)-4',5'-didehydro-5'-deoxy-5'-fluoroadenosine. Journal of Biological Chemistry, 268 , 17030-17037.
31. De Clercq, E. (2005). John Montgomery's legacy: Carbocyclic adenosine analogues as SAH hydrolase inhibitors with broad-spectrum antiviral activity. Nucleosides, Nucleotides and Nucleic Acids, 24 , 1395-1415.
32. Madhavan, G. V. B., Martin, J. C. (1986). A novel and stereospecific synthesis of (+/-)-and (-)-aristeromycin. The Journal of Organic Chemistry, 51 , 1287-1293.
33. Cermak, R. C., Vince, R. (1981). (±) 4β-amino-2a, 3a-dihydroxy-1β-cyclopentanemethanol hydrochloride. Carbocyclic ribofuranosylamine for the synthesis of carbocyclic nucleosides. Tetrahedron Letters, 22 , 2331-2332.
34. Maggini, M., Prato, M., Scorrano, G. (1990). Imino diels-alder cycloadditions: An application to the synthesis of (±)-aristeromycin. Tetrahedron Letters, 31 , 6243-6246.
35. Palmer, C. F., Parry, K. P., Roberts, S. M. (1990). Synthesis of carbocyclic clitocine. Tetrahedron Letters, 31 , 279-282.
36. Shealy, Y. F., Clayton, J. D. (1969). Synthesis of carbocyclic analogs of purine ribonucleosides. Journal of the American Chemical Society, 91 , 3075-3083.
37. Trost, B. M., Kuo, G. H., Benneche, T. (1988). Transition-metal-controlled synthesis of (.+-. )-aristeromycin and (.+-. )-2',3'-diepi-aristeromycin. An unusual directive effect in hydroxylations. Journal of the American Chemical Society, 110 , 621-622.
38. Arita, M., Adachi, K., Ito, Y., Sawai, H., Ohno, M. (1983). Enantioselective synthesis of the carbocyclic nucleosides (-) -aristeromycin and (-) -neplanocin a by a chemicoenzymatic approach. Journal of the American Chemical Society, 105 , 4049-4055.
39. Arai, Y., Hayashi, K., Koizumi, T., Shiro, M., Kuriyama, K. (1988). Dimethyl (R)S-2-(10-isobornylsulfinyl)maleate, a chiral synthetic equivalent of dimethyl acetylenedicarboxylate: Preparation and its application to the formal chiral synthesis of (-) -neplanocin a and (-) -aristeromycin. Tetrahedron Letters, 29 , 6143-6146.
40. Arai, Y., Hayashi, Y., Yamamoto, M., Takayema, H., Koizumi, T. (1988). An enantioconvergent route to carbocyclic nucleosides (-) -aristeromycin and (-) -neplanocin a via the asymmetric Diels-Alder reaction. Journal of the Chemical Society, Perkin Transactions 1 , 1988 , 3133-3140.
41. Boyer, S. J., Leahy, J. W. (1997). Carbocyclic nucleoside analogs. 1. Concise enantioselective synthesis of functionalized cyclopentanes and formal total synthesis of aristeromycin. The Journal of Organic Chemistry, 62 , 3976-3980.
42. Brown, B., Hegedus, L. S. (2000). A novel, one-pot ring expansion of cyclobutanones. Syntheses of carbovir and aristeromycin. The Journal of Organic Chemistry, 65 , 1865-1872.
43. Deardorff, D. R., Savin, K. A., Justman, C. J., Karanjawala, Z. E., Sheppeck, J. E., Hager, D. C., Aydin, N. (1996). Conversion of allylic alcohols into allylic nitromethyl compounds via a palladium-catalyzed solvolysis: An enantioselective synthesis of an advanced carbocyclic nucleoside precursor. The Journal of Organic Chemistry, 61 , 3616-3622.
44. Trost, B. M., Madsen, R., Guile, S. D., Brown, B. (2000). Palladium-catalyzed enantioselective synthesis of carbanucleosides. Journal of the American Chemical Society, 122 , 5947-5956.
45. Trost, B. M., Surivet, J.-P. (2000). Asymmetric alkylation of nitroalkanes13. Angewandte Chemie, 39 , 3122-3124.
46. Borcherding, D. R., Scholtz, S. A., Borchardt, R. T. (1987). Synthesis of analogs of neplanocin A: Utilization of optically active dihydroxycyclopentenones derived from carbohydrates. The Journal of Organic Chemistry, 52 , 5457-5461.
47. Wolfe, M. S., Borcherding, D. R., Borchardt, R. T. (1989). A 9-step enantiospecific synthesis of (-) -aristeromycin from d-ribonic acid ?-lactone. Tetrahedron Letters, 30 , 1453-1456.
48. Jin, Y. H., Chu, C. K. (2002). Efficient and practical synthesis of d-cyclopent-2-enone, the key intermediate for the synthesis of carbocyclic nucleosides. Tetrahedron Letters, 43 , 4141-4143.
49. Jin, Y. H., Liu, P., Wang, J., Baker, R., Huggins, J., Chu, C. K. (2003). Practical synthesis of D-and L-2-cyclopentenone and their utility for the synthesis of carbocyclic antiviral nucleosides against orthopox viruses (smallpox, monkeypox, and cowpox virus). The Journal of Organic Chemistry, 68 , 9012-9018.
50. Wang, P., Agrofoglio, L. A., Gary Newton, M., Chu, C. K. (1997). Asymmetric synthesis of L-cyclopentyl carbocyclic nucleosides. Tetrahedron Letters, 38 , 4207-4210.
51. Wang, P., Agrofoglio, L. A., Newton, M. G., Chu, C. K. (1999). Chiral synthesis of carbocyclic analogues of L-ribofuranosides. The Journal of Organic Chemistry, 64 , 4173-4178.
52. Yang, M., Ye, W., Schneller, S. W. (2004). Preparation of carbocyclic S -adenosylazamethionine accompanied by a practical synthesis of (-) -aristeromycin. The Journal of Organic Chemistry, 69 , 3993-3996.
53. Marquez, V. E., Lim, M. I., Tseng, C. K. H., Markovac, A., Priest, M. A., Khan, M. S., Kaskar, B. (1988). Total synthesis of (-) -neplanocin A. The Journal of Organic Chemistry, 53 , 5709-5714.
54. Camps, P., Cardellach, J., Font, J., Ortuño, R. M., Ponsati, O. (1982). Studies on structurally simple a, β-butenolides-ii: (-) -(S)-?-hydroxymethyl-a, β-butenolide and derivatives from D-ribonolactone efficient synthesis of (-) -ranunculin. Tetrahedron, 38 , 2395-2402.
55. Medich, J. R., Kunnen, K. B., Johnson, C. R. (1987). Synthesis of the carbocyclic nucleoside (-) -neplanocin A. Tetrahedron Letters, 28 , 4131-4134.
56. Song, G. Y., Paul, V., Choo, H., Morrey, J., Sidwell, R. W., Schinazi, R. F., Chu, C. K. (2001). Enantiomeric synthesis of D-and L-cyclopentenyl nucleosides and their antiviral activity against HIV and West Nile Virus. Journal of Medicinal Chemistry, 44 , 3985-3993.
57. Michel, B. Y., Strazewski, P. (2007). Synthesis of (-) -neplanocin A with the highest overall yield via an efficient mitsunobu coupling. Tetrahedron, 63 , 9836-9841.
58. Bennett Jr., L., Allan, P. W., Hill, D. L. (1968). Metabolic studies with carbocyclic analogs of purine nucleosides. Molecular Pharmacology, 4 , 208-217.
59. Glazer, R., Knode, M. (1984). Neplanocin a. A cyclopentenyl analog of adenosine with specificity for inhibiting RNA methylation. Journal of Biological Chemistry, 259 , 12964-12969.
60. Glazer, R. I., Knode, M. C., Tseng, C. K. H., Haines, D. R., Marquez, V. E. (1986). 3-deazaneplanocin A: A new inhibitor of S -adenosylhomocysteine synthesis and its effects in human colon carcinoma cells. Biochemical Pharmacology, 35 , 4523-4527.
61. Keller, B., Clark, R., Pegg, A., Borchardt, R. (1985). Purification and characterization of some metabolic effects of S-neplanocylmethionine. Molecular Pharmacology, 28 , 364-370.
62. Li,W., Yin, X., Schneller, S. W. (2008). 5'-fluoro-5'-deoxyaristeromycin. Bioorganic & Medicinal Chemistry Letters, 18 , 220-222.
63. Ando, T., Iwata, M., Zulfiqar, F., Miyamoto, T., Nakanishi, M., Kitade, Y. (2008). Synthesis of 2-modified aristeromycins and their analogs as potent inhibitors against Plasmodium falciparum S -adenosyl-L-homocysteine hydrolase. Bioorganic & Medicinal Chemistry, 16 , 3809-3815.
64. Kitade, Y., Ando, T., Yamaguchi, T., Hori, A., Nakanishi, M., Ueno, Y. (2006). 4'-fluorinated carbocyclic nucleosides: Synthesis and inhibitory activity against S -adenosyl-L-homocysteine hydrolase. Bioorganic & Medicinal Chemistry, 14 , 5578-5583.
65. Ando, T., Kojima, K., Chahota, P., Kozaki, A., Milind, N. D., Kitade, Y. (2008). Synthesis of 4'-modified noraristeromycins to clarify the effect of the 4'-hydroxyl groups for inhibitory activity against S -adenosyl-L-homocysteine hydrolase. Bioorganic & Medicinal Chemistry Letters, 18 , 2615-2618.
66. Patil, S. D., Schneller, S. W., Hosoya, M., Snoeck, R., Andrei, G., Balzarini, J., De Clercq, E. (1992). The synthesis and antiviral properties of (+/-) -5'-noraristeromycin and related purine carbocyclic nucleosides. A new lead for anti-human cytomegalovirus agent design. Journal of Medicinal Chemistry, 35 , 3372-3377.
67. Siddiqi, S. M., Chen, X., Schneller, S. W., Ikeda, S., Snoeck, R., Andrei, G., Balzarini, J., De Clercq, E. (1994). Antiviral enantiomeric preference for 5'-noraristeromycin. Journal of Medicinal Chemistry, 37 , 551-554.
68. Siddiqi, S. M., Chen, X., Schneller, S. W., Ikeda, S., Snoeck, R., Andrei, G., Balzarini, J., De Clercq, E. (1994). An epimer of 5'-noraristeromycin and its antiviral properties. Journal of Medicinal Chemistry, 37 , 1382-1384.
69. Yang, M., Schneller, S. W., Korba, B. (2005). 5'-homoneplanocin A inhibits hepatitis B and hepatitis C. Journal of Medicinal Chemistry, 48 , 5043-5046.
70. Yin, X.-q., Li, W.-k., Yang, M., Schneller, S. W. (2009). A new synthesis and an antiviral assessment of the 4'-fluoro derivative of 4'-deoxy-5'-noraristeromycin. Bioorganic & Medicinal Chemistry, 17 , 3126-3129.
71. Ault-Riche, D., Lee, Y., Yuan, C., Hasobe, M., Wolfe, M., Borcherding, D., Borchardt, R. (1993). Effects of 4'-modified analogs of aristeromycin on the metabolism of S -adenosyl-L-homocysteine in murine l929 cells. Molecular Pharmacology, 43 , 989-997.
72. Hasobe, M., Liang, H., Ault-Riche, D., Borcherding, D., Wolfe, M., Borchardt, R. (1993). (1'R, 2'S, 3'R)-9-(2', 3'-dihydroxycyclopentan-1'-yl)-adenine and-3-deazaadenine: Analogues of aristeromycin which exhibit potent antiviral activity with reduced cytotoxicity. Antiviral Chemistry & Chemotherapy, 4 , 245-248.
73. Das, S. R., Schneller, S. W., Balzarini, J., De Clercq, E. (2002). A mercapto analogue of 5'-noraristeromycin. Bioorganic & Medicinal Chemistry, 10 , 457-460.
74. Rajappan, V. P., Schneller, S. W. (2003). 5'-amino-5'-deoxyaristeromycin and its antiviral properties. Bioorganic & Medicinal Chemistry, 11 , 5199-5201.
75. Roy, A., Schneller, S. W. (2003). 4'-and 1'-methyl-substituted 5'-norcarbanucleosides. The Journal of Organic Chemistry, 68 , 9269-9273.
76. Roy, A., Serbessa, T., Schneller, S. W. (2006). 3'-Fluoro-3'-deoxy-5'-noraristeromycin derivatives: Synthesis and antiviral analysis. Bioorganic & Medicinal Chemistry, 14 , 4980-4986.
77. Yin, X.-q., Schneller, S. W. (2005). 5'-Noraristeromycin derivatives isomeric to aristeromycin and 2'-deoxyaristeromycin. Tetrahedron, 61 , 1839-1843.
78. Seley-Radtke, K. L., Sunkara, N. K. (2009). Carbocyclic thymidine analogs for use as potential therapeutic agents. Nucleosides, Nucleotides & Nucleic Acids, 28 , 633-641.
79. Carroll, S., Tomassini, J., Bosserman, M., Getty, K., Stahlhut, M., Eldrup, A., Bhat, B., Hall, D., Simcoe, A., LaFemina, R. (2003). Inhibition of hepatitis C virus RNA replication by 2-modified nucleoside analogs. Journal of Biological Chemistry, 278 , 11979-11984.
80. 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. (2004). Structure-activity relationship of purine ribonucleosides for inhibition of hepatitis C virus RNA-dependent RNA polymerase. Journal of Medicinal Chemistry, 47 , 2283-2295.
81. Ko, O. H., Hong, J. H. (2009). Synthesis and in vitro activity evaluation of 2',3'-C-dimethyl carbocyclic nucleoside analogues as potential anti-HCV agents. Nucleosides, Nucleotides & Nucleic Acids, 28 , 761-771.
82. Madhavan, G. V. B., McGee, D. P. C., Rydzewski, R. M., Boehme, R., Martin, J. C., Prisbe, E. J. (1988). Synthesis and antiviral evaluation of 6'-substituted aristeromycins: Potential mechanism-based inhibitors of S -adenosylhomocysteine hydrolase. Journal of Medicinal Chemistry, 31 , 1798-1804.
83. Yin, X.-q., Schneller, S. W. (2005). Chiral syntheses of 6'-β-fluoroaristeromycin, 6'-β-fluoro-5'-noraristeromycin and aristeromycin. Tetrahedron Letters, 46 , 7535-7538.
84. Chiang, P., Richards, H., Cantoni, G. (1977). S -adenosyl-L-homocysteine hydrolase: Analogues of S -adenosyl-L-homocysteine as potential inhibitors. Molecular Pharmacology, 13 , 939-947.
85. De Clercq, E., Montgomery, J. A. (1983). Broad-spectrum antiviral activity of the carbocyclic analog of 3-deazaadenosine. Antiviral Research, 3 , 17-24.
86. Siddiqi, S. M., Chen, X., Rao, J., Schneller, S. W., Ikeda, S., Snoeck, R., Andrei, G., Balzarini, J., De Clercq, E. (1995). 3-Deaza-and 7-deaza-5'-noraristeromycin and their antiviral properties. Journal of Medicinal Chemistry, 38 , 1035-1038.
87. Lin, W., Gupta, A., Kim, K. H., Mendel, D., Miller, M. J. (2009). Syntheses of new spirocarbocyclic nucleoside analogs using iminonitroso diels-alder reactions. Organic Letters, 11 , 449-452.
88. Lin, W., Virga, K. G., Kim, K.-H., Zajicek, J., Mendel, D., Miller, M. J. (2009). Diastereoselective synthesis of a spiro-noraristeromycin using an acyl-nitroso Diels-Alder reaction. Journal of Organic Chemistry, 74 , 5941-5946.
89. Kojima, H., Kozaki, A., Iwata, M., Ando, T., Kitade, Y. (2008). Synthesis of 3',4'-epoxynoraristeromycin analogs for molecular labeling probe of S -adenosyl-L-homocysteine hydrolase. Bioorganic & Medicinal Chemistry, 16 , 6575-6579.
90. Sadler, J. M., Mosley, S. L., Dorgan, K. M., Zhou, Z. S., Seley-Radtke, K. L. (2009). Synthetic strategies toward carbocyclic purine-pyrimidine hybrid nucleosides. Bioorganic & Medicinal Chemistry, 17 , 5520-5525.
91. Li, H., Yoo, J. C., Hong, J. H. (2009). Synthesis and anti-HCV evaluation of 4'a-ethyl and 2'β-methyl-carbodine analogs. Nucleosides, Nucleotides & Nucleic Acids, 28 , 809-820.
92. Rao, J. R., Jha, A. K., Rawal, R. K., Sharon, A., Day, C.W., Barnard, D. L., Smee, D. F., Chu, C. K. (2010). (-) -Carbodine: Enantiomeric synthesis and in vitro antiviral activity against various strains of influenza virus including H5N1 (avian influenza) and novel 2009 H1N1 (swine flu). Bioorganic & Medicinal Chemistry Letters, 20 , 2601-2604.
93. Kim, Y. A., Rawal, R. K., Yoo, J., Sharon, A., Jha, A. K., Chu, C. K., Rais, R. H., Al Safarjalani, O. N., Naguib, F. N. M., el Kouni, M. H. (2010). Structure-activity relationships of carbocyclic 6-benzylthioinosine analogues as subversive substrates of Toxoplasma gondii adenosine kinase. Bioorganic & Medicinal Chemistry, 18 , 3403-3412.
94. Obara, T., Shuto, S., Saito, Y., Snoeck, R., Andrei, G., Balzarini, J., De Clercq, E., Matsuda, A. (1996). New neplanocin analogues. 7. Synthesis and antiviral activity of 2-halo derivatives of neplanocin A. Journal of Medicinal Chemistry, 39 , 3847-3852.
95. Shuto, S., Obara, T., Itoh, H., Kosugi, Y., Saito, Y., Toriya, M., Yaginuma, S., Shigeta, S., Matsuda, A. (1994). New neplanocin analogues. IV: 2-fluoroneplanocin A: An adenosine deaminase-resistant equivalent of neplanocin A. Chemical and Pharmaceutical Bulletin, 42 , 1688-1690.
96. Andrei, G., De Clercq, E. (1990). Inhibitory effect of selected antiviral compounds on arenavirus replication in vitro. Antiviral Research, 14 , 287-299.
97. Shigeta, S., Mori, S., Baba, M., Ito, M., Honzumi, K., Nakamura, K., Oshitani, H., Numazaki, Y., Matsuda, A., Obara, T. (1992). Antiviral activities of ribavirin, 5-ethynyl-1-β-d -ribofuranosylimidazole-4-carboxamide, and 6'-(r)-6'-Cmethylneplanocin a against several ortho-and paramyxoviruses. Antimicrobial Agents and Chemotherapy, 36 , 435-439.
98. Shuto, S., Obara, T., Toriya, M., Hosoya, M., Snoeck, R., Andrei, G., Balzarini, J., De Clercq, E. (1992). New neplanocin analogs. 1. Synthesis of 6'-modified neplanocin A derivatives as broad-spectrum antiviral agents. Journal of Medicinal Chemistry, 35 , 324-331.
99. Shuto, S., Minakawa, N., Niizuma, S., Kim, H.-S., Wataya, Y., Matsuda, A. (2002). New neplanocin analogues. 12. Alternative synthesis and antimalarial effect of (6'R)-6'-C-methylneplanocin A, a potent AdoHcy hydrolase inhibitor. Journal of Medicinal Chemistry, 45 , 748-751.
100. Hasobe, M., McKee, J. G., Borcherding, D. R., Borchardt, R. T. (1987). 9-(Trans-2',trans-3'-dihydroxycyclopent-4'-enyl)-adenine and -3-deazaadenine: Analogs of neplanocin A which retain potent antiviral activity but exhibit reduced cytotoxicity. Antimicrobial Agents and Chemotherapy, 31 , 1849-1851.
101. Ye, W., He, M., Schneller, S. W. (2009). Synthesis of the 6'-iso analogs of neplanocin A and 5'-homoneplanocin A. Tetrahedron Letters, 50 , 7156-7158.
102. Shuto, S., Obara, T., Saito, Y., Andrei, G., Snoeck, R., De Clercq, E., Matsuda, A. (1996). New neplanocin analogues. 6. Synthesis and potent antiviral activity of 6'-homoneplanocin A. Journal of Medicinal Chemistry, 39 , 2392-2399.
103. Park, A.-Y., Kim, K. R., Lee, H.-R., Kang, J.-A., Kim, W. H., Jeong, L. S., Moon, H. R. (2008). Synthesis and biological evaluation of 5''-iodoneplanocin A and its analogs. Nucleic Acids Symposium Series, 52 , 653-654.
104. Park, A.-Y., Kim, K. R., Lee, H.-R., Kang, J.-A., Kim, W. H., Chun, P., Ahmad, P., Jeong, L. S., Moon, H. R. (2008). Design and synthesis of 5''-iodoneplanocin A and its analogues as potential S -adenosylhomocysteine hydrolase inhibitor. Bulletin of the Korean Chemical Society, 29 , 2487-2490.
105. Lee, H.-R., Kang, J.-A., Park, A.-Y., Kim, W. H., Chun, P., Kim, J., Kim, J.-A., Lee, B., Jeong, L. S., Moon, H. R. (2009). Synthesis of neplanocin A analog with 2'-"up"-C-methyl substituent as potential anti-HCV agent. Bulletin of the Korean Chemical Society, 30 , 2043-2050.
106. Radi, M., Rao, J. R., Jha, A. K., Chu, C. K. (2009). A convergent approach for the synthesis of ara-neplanocin A analogs under sub-zero microwave assisted conditions. Nucleosides, Nucleotides & Nucleic Acids, 28 , 504-518.
107. Chu, C. K., Jin, Y. H., Baker, R. O., Huggins, J. (2003). Antiviral activity of cyclopentenyl nucleosides against orthopox viruses (smallpox, monkeypox and cowpox). Bioorganic & Medicinal Chemistry Letters, 13 , 9-12.
108. Park, Y. H., Choi, W. J., Tipnis, A. S., Lee, K. M., Jeong, L. S. (2009). Truncated fluorocyclopentenyl pyrimidines as S -adenosylhomocysteine hydrolase inhibitors. Nucleosides, Nucleotides & Nucleic Acids, 28 , 601-613.
109. Jeong, L. S., Lee, J. A., Moon, H. R., Kim, H. O., Lee, K. M., Lee, H. J., Chun, M. W. (2007). Asymmetric synthesis of novel apio carbocyclic nucleoside analogues as potential antiviral and antitumor agent. Nucleosides, Nucleotides & Nucleic Acids, 26 , 721-724.
110. Park, A.-Y., Moon, H. R., Kim, K. R., Kang, J.-A., Chun, M. W., Jeong, L. S. (2007). Asymmetric synthesis of apio fluoroneplanocin a analogs as potential adohcy hydrolase inhibitor. Nucleosides, Nucleotides & Nucleic Acids, 26 , 943-947.
111. Rao, J. R., Schinazi, R. F., Chu, C. K. (2007). Enantioselective synthesis and antiviral activity of purine and pyrimidine cyclopentenyl C-nucleosides. Bioorganic & Medicinal Chemistry, 15 , 839-846.
112. Cho, J. H., Bernard, D. L., Sidwell, R. W., Kern, E. R., Chu, C. K. (2006). Synthesis of cyclopentenyl carbocyclic nucleosides as potential antiviral agents against orthopoxviruses and sars. Journal of Medicinal Chemistry, 49 , 1140-1148.
113. Arumugham, B., Kim, H.-J., Prichard, M. N., Kern, E. R., Chu, C. K. (2006). Synthesis and antiviral activity of 7-deazaneplanocin A against orthopoxviruses (vaccinia and cowpox virus). Bioorganic & Medicinal Chemistry Letters, 16 , 285-287.
114. Kim, H.-J., Sharon, A., Bal, C., Wang, J., Allu, M., Huang, Z., Murray, M. G., Bassit, L., Schinazi, R. F., Korba, B., Chu, C. K. (2009). Synthesis and anti-hepatitis B virus and anti-hepatitis C virus activities of 7-deazaneplanocin A analogues in vitro. Journal of Medicinal Chemistry, 52 , 206-213.
115. Bodenteich, M., Marquez, V. E., Hallows, W. H., Goldstein, B. M. (1992). Synthesis and structural determination of (+/-) -neplanocin F. The Journal of Organic Chemistry, 57 , 2071-2076.
116. Comin, M. J., Leitofuter, J., Rodríguez, J. B. (2002). Enantioselective synthesis of (+)-neplanocin F. Tetrahedron, 58 , 3129-3136.
117. Comin, M. J., Rodriguez, J. B. (2000). First synthesis of (-) -neplanocin C. Tetrahedron, 56 , 4639-4649.
118. Rodriguez, S., Edmont, D., Mathé, C., Périgaud, C. (2007). First enantioselective synthesis of (-) -neplanocin F. Tetrahedron, 63 , 7165-7171.
119. Zhang, H., Schinazi, R. F., Chu, C. K. (2006). Synthesis of neplanocin F analogues as potential antiviral agents. Bioorganic & Medicinal Chemistry, 14 , 8314-8322.
120. 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. (1988). Potent and selective activity of a new carbocyclic nucleoside analog (carbovir: NSC 614846) against human immunodeficiency virus in vitro. Biochemical and Biophysical Research Communications, 156 , 1046-1053.
121. Miller, W., Daluge, S., Garvey, E., Hopkins, S., Reardon, J., Boyd, F., Miller, R. (1992). Phosphorylation of carbovir enantiomers by cellular enzymes determines the stereoselectivity of antiviral activity. Journal of Biological Chemistry, 267 , 21220-21224.
122. Brouwer, K., St. Claire, R., Lagarde, J., Patanella, J., Walsh, J., Miwa, G. (1990). The pharmacokinetics of (-) -carbovir in rats. Evidence for nonlinear elimination. Drug Metabolism and Disposition, 18 , 1078-1083.
123. Daluge, S., Good, S., Faletto, M., Miller, W., St. Clair, M., Boone, L., Tisdale, M., Parry, N., Reardon, J., Dornsife, R., Averett, D., Krenitsky, T. (1997). 1592u89, a novel carbocyclic nucleoside analog with potent, selective anti-human immunodeficiency virus activity. Antimicrobial Agents and Chemotherapy, 41 , 1082-1093.
124. Shu-hui, H., Rory, P. R., Cheryl, L. Z. (1991). The bioavailability and nonlinear clearance of (-) -carbovir in the rat. Pharmaceutical Research, 8 , 739-743.
125. Faletto, M., Miller, W., Garvey, E., St. Clair, M., Daluge, S., Good, S. (1997). Unique intracellular activation of the potent anti-human immunodeficiency virus agent 1592u89. Antimicrobial Agents and Chemotherapy, 41 , 1099-1107.
126. Vince, R., Hua, M. (1990). Synthesis and anti-hiv activity of carbocyclic 2',3'-didehydro-2',3'-dideoxy 2,6-disubstituted purine nucleosides. Journal of Medicinal Chemistry, 33 , 17-21.
127. Shealy, Y., Clayton, J. (1973). Carbocyclic analogs of guanosine and 8-azaguanosine. Journal of Pharmaceutical Sciences, 62 , 1432-1434.
128. Evans, C., Roberts, S., Shoberu, K., Sutherland, A. (1992). Potential use of carbocyclic nucleosides for the treatment of aids: Chemo-enzymatic syntheses of the enantiomers of carbovir. Journal of the Chemical Society. Perkin transactions. I , 589-592.
129. Taylor, S., Sutherland, A., Lee, C., Wisdom, R., Thomas, S., Roberts, S., Evans, C. (1990). Chemoenzymatic synthesis of (-) -carbovir utilizing a whole cell catalyzed resolution of 2-azabicyclo [2.2. 1] hept-5-en-3-one. Journal of the Chemical Society. Chemical Communications, 1120-1121.
130. Sicsic, S., Ikbal, M., Le Goffic, F. (1987). Chemoenzymatic approach to carbocyclic analogues of ribonucleosides and nicotinamide ribose. Tetrahedron Letters, 28 , 1887-1888.
131. Jones, M., Myers, P., Robertson, C., Storer, R., Williamson, C. (1991). Total synthesis of (-) -carbovir. Journal of the Chemical Society, Perkin Transactions 1 , 1991 , 2479-2484.
132. Crimmins, M. T., King, B. W. (1996). An efficient asymmetric approach to carbocyclic nucleosides: Asymmetric synthesis of 1592u89, a potent inhibitor of HIV reverse transcriptase. The Journal of Organic Chemistry, 61 , 4192-4193.
133. Crimmins, M. T., Zuercher, W. J. (2000). Solid-phase synthesis of carbocyclic nucleosides. Organic Letters, 2 , 1065-1067.
134. Trost, B., Madsen, R., Guile, S., Elia, A. (1996). A short enantioselective synthesis of carbanucleosides. Angewandte Chemie International Edition in English, 35 , 1569-1572.
135. Vazquez-Romero, A., Rodriguez, J., Lledo, A., Verdaguer, X., Riera, A. (2008). Enantioselective syntheses of carbanucleosides from the Pauson-Khand adduct of trimethylsilylacetylene and norbornadiene. Organic Letters, 10 , 4509-4512.
136. Sola, J., Reves, M., Riera, A., Verdaguer, X. (2007). N-phosphino sulfinamide ligands: An efficient manner to combine sulfur chirality and phosphorus coordination behavior. Angewandte Chemie-International Edition, 46 , 5020-5023.
137. Wang, P., Schinazi, R. F., Chu, C. K. (1998). Asymmetric synthesis and anti-HIV activity of L-carbocyclic 2',3'-didehydro-2',3'-dideoxyadenosine. Bioorganic & Medicinal Chemistry Letters, 8 , 1585-1588.
138. Huang, W., Miller, M. J., Clercq, E. D., Balzarini, J. (2007). Syntheses and anti-HIV activities of (±)-norcarbovir and (±)-norabacavir. Organic & Biomolecular Chemistry, 5 , 1164-1166.
139. Katagiri, N., Nomura, M., Sato, H., Kaneko, C., Yusa, K., Tsuruo, T. (1992). Synthesis and anti-HIV activity of 9-[C-4,t-5-bis(hydroxymethyl)cyclopent-2-en-R-1-yl]-9H-adenine. Journal of Medicinal Chemistry, 35 , 1882-1886.
140. Katagiri, N., Toyota, A., Shiraishi, T., Sato, H., Kaneko, C. (1992). Synthesis of (1R, 4S, 5R)-9-(4,5-bishydroxy-methylcyclopent-2-en-1-yl)-9h-adenine [(-)-BCA] and selective inhibition of human immunodeficiency virus. Tetrahedron Letters, 33 , 3507-3510.
141. Tanaka, M., Norimine, Y., Fujita, T., Suemune, H., Sakai, K. (1996). Chemoenzymatic synthesis of antiviral carbocyclic nucleosides: Asymmetric hydrolysis of meso-3,5-bis(acetoxymethyl)cyclopentenes using Rhizopus delemar lipase. The Journal of Organic Chemistry, 61 , 6952-6957.
142. Kumamoto, H., Takahashi, N., Shimamura, T., Tanaka, H., Nakamura, K. T., Hamasaki, T., Baba, M., Abe, H., Yano, M., Kato, N. (2008). Synthesis of (+-) -9-[C-4, t-5-bis(hydroxymethyl)cyclopent-2-en-r-1-yl]-9H-adenine (BCA) derivatives branched at the 4'-position based on intramolecular sh 2' cyclization. Tetrahedron, 64 , 1494-1505.
143. Toyota, A., Nishimura, A., Kaneko, C. (1998). . A-fluorination of 6-phenylsulfinyl-2-azabicyclo[2.2.1]heptan-3-one and synthesis of 2'-fluoro substituted carbovir. Tetrahedron Letters, 39 , 4687-4690.
144. Wang, J., Jin, Y., Rapp, K. L., Bennett, M., Schinazi, R. F., Chu, C. K. (2005). Synthesis, antiviral activity, and mechanism of drug resistance of d-and l-2',3'-didehydro-2',3'-dideoxy-2'-fluorocarbocyclic nucleosides. Journal of Medicinal Chemistry, 48 , 3736-3748.
145. Wang, J., Jin, Y., Rapp, K. L., Schinazi, R. F., Chu, C. K. (2007). d-and l-2',3'-didehydro-2',3'-dideoxy-3'-fluoro-carbocyclic nucleosides: Synthesis, anti-HIV activity and mechanism of resistance. Journal of Medicinal Chemistry, 50 , 1828-1839.
146. Hegedus, L. S., Cross, J. (2004). Synthesis of 4'-methyl and 4'-cyano carbocyclic 2',3'-didehydro nucleoside analogues via 1,4-addition to substituted cyclopentenones. The Journal of Organic Chemistry, 69 , 8492-8495.
147. Kumamoto, H., Haraguchi, K., Tanaka, H., Kato, K., Nitanda, T., Baba, M., Dutschman, G. E., Cheng, Y.-C. (2005). Synthesis of (+/-) -4'-ethynyl and 4'-cyano carbocyclic analogues of stavudine (d4T). Nucleosides, Nucleotides and Nucleic Acids, 24 , 73-83.
148. Kim, J. W., Hong, J. H. (2005). Synthesis and antiviral evaluation of novel 6'a-methyl-branched carbovir analogues. Archiv der Pharmazie, 338 , 399-404.
149. Li, H., Hong, J. H. (2008). An efficient synthesis of 4'-vinylated carboxylic nucleoside analogues via two directional ring-closing metathesis. Bulletin of the Korean Chemical Society, 29 , 993-997.
150. Kim, A., Hong, J. H. (2007). Efficient construction of quaternary carbon: Stereocontrolled synthesis of novel abacavir analogue. Bulletin of the Korean Chemical Society, 28 , 1545-1548.
151. Jha, A. K., Sharon, A., Rondla, R., Chu, C. K. (2009). Regioselective synthesis of 3-deazacarbovir and its 3-deaza-adenosine analogues. Tetrahedron, 65 , 9362-9367.
152. Liu, L. J., Ko, O. H., Hong, J. H. (2008). Synthesis and anti-HIV-1 activity of carbocyclic versions of stavudine analogues using a ring-closing metathesis. Bulletin of the Korean Chemical Society, 29 , 1723-1728.
153. Kumamoto, H., Haraguchi, K., Ida, M., Nakamura, K. T., Kitagawa, Y., Hamasaki, T., Baba, M., Matsubayashi, S. S., Tanaka, H. (2009). Synthesis of (±)-4'-ethynyl-5',5'-difluoro-2',3'-dehydro-3'-deoxy-carbocyclic thymidine: A difluoromethylidene analog of promising anti-HIV agent ed4T. Tetrahedron, 65 , 7630-7636.
154. Liu, L. J., Hong, J. H. (2009). Synthesis and anti-HIV activity of 4'-modified cyclopentenyl pyrimidine C-nucleosides. Nucleosides, Nucleotides & Nucleic Acids, 28 , 303-314.
155. Ko, O. H., Hong, J. H. (2002). Efficient synthesis of novel carbocyclic nucleosides via sequential claisen rearrangement and ring-closing metathesis. Tetrahedron Letters, 43 , 6399-6402.
156. Yang, Y.-Y., Xu, J., You, Z.-W., Xu, X.-h., Qiu, X.-L., Qing, F.-L. (2007). Synthesis of 3',3'-difluoro-2'-hydroxymethyl-4',5'-unsaturated carbocyclic nucleosides. Organic Letters, 9 , 5437-5440.
157. Boojamra, C. G., Parrish, J. P., Sperandio, D., Gao, Y., Petrakovsky, O. V., Lee, S. K., Markevitch, 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., Mackman, R. L. (2009). Design, synthesis, and anti-HIV activity of 4'-modified carbocyclic nucleoside phosphonate reverse transcriptase inhibitors. Bioorganic & Medicinal Chemistry, 17 , 1739-1746.
158. Zoulim, F. (2006). Entecavir: A new treatment option for chronic hepatitis B. Journal of Clinical Virology, 36 , 8-12.
159. Yamanaka, G., Wilson, T., Innaimo, S., Bisacchi, G. S., Egli, P., Rinehart, J. K., Zahler, R., Colonno, R. J. (1999). Metabolic studies on BMS-200475, a new antiviral compound active against hepatitis B virus. Antimicrobial Agents and Chemotherapy, 43 , 190-193.
160. Seifer, M., Hamatake, R., Colonno, R., Standring, D. (1998). In vitro inhibition of hepadnavirus polymerases by the triphosphates of BMS-200475 and lobucavir. Antimicrobial Agents and Chemotherapy, 42 , 3200-3208.
161. Bisacchi, G. S., Chao, S. T., Bachard, C., Daris, J. P., Innaimo, S., Jacobs, G. A., Kocy, O., Lapointe, P., Martel, A., Merchant, Z., Slusarchyk, W. A., Sundeen, J. E., Young, M. G., Colonno, R., Zahler, R. (1997). BMS-200475, a novel carbocyclic 2'-deoxyguanosine analog with potent and selective anti-hepatitis B virus activity in vitro. Bioorganic & Medicinal Chemistry Letters, 7 , 127-132.
162. Innaimo, S., Seifer, M., Bisacchi, G., Standring, D., Zahler, R., Colonno, R. (1997). Identification of BMS-200475 as a potent and selective inhibitor of hepatitis B virus. Antimicrobial Agents and Chemotherapy, 41 , 1444-1448.
163. Slusarchyk, W., Field, A., Greytok, J., Taunk, P., Tuomari, A., Young, M., Zahler, R. (1992). 4-Hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl purines and pyrimidines, a new class of anti-herpesvirus agents. Antiviral Research, 17 (S1 ), 98.
164. Yang, H., Qi, X., Sabogal, A., Miller, M., Xiong, S., Delaney, W. (2005). Crossresistance testing of next-generation nucleoside and nucleotide analogues against lamivudine-resistant HBV. Antiviral Therapy, 10 , 625-633.
165. Ono, S. K., Kato, N., Shiratori, Y., Kato, J., Goto, T., Schinazi, R. F., Carrilho, F. J., Omata, M. (2001). The polymerase l528m mutation cooperates with nucleotide binding-site mutations, increasing hepatitis B virus replication and drug resistance. The Journal of Clinical Investigation, 107 , 449-455.
166. Levine, S., Hernandez, D., Yamanaka, G., Zhang, S., Rose, R., Weinheimer, S., Colonno, R. (2002). Efficacies of entecavir against lamivudine-resistant hepatitis B virus replication and recombinant polymerases in vitro. Antimicrobial Agents and Chemotherapy, 46 , 2525-2532.
167. Chang, T., Gish, R., de Man, R., Gadano, A., Sollano, J., Chao, Y., Lok, A., Han, K., Goodman, Z., Zhu, J. (2006). A comparison of entecavir and lamivudine for HBeAg-positive chronic hepatitis B. The New England Journal of Medicine, 354 , 1001-1010.
168. Lai, C., Shouval, D., Lok, A., Chang, T., Cheinquer, H., Goodman, Z., DeHertogh, D., Wilber, R., Zink, R., Cross, A. (2006). Entecavir versus lamivudine for patients with HBeAg-negative chronic hepatitis B. The New England Journal of Medicine, 354 , 1011.
169. Colonno, R., Rose, R., Levine, S., Baldick, J., Pokornowski, K., Plym, M., Yu, C., Mazzucco, C., Fang, J., Hsu, M. (2005). Entecavir two year resistance update: No resistance observed in nucleoside naive patients and low frequency resistance emergence in lamivudine refractory patients. Hepatology, 42 , 573A.
170. Tenney, D., Levine, S., Rose, R., Walsh, A., Weinheimer, S., Discotto, L., Plym, M., Pokornowski, K., Yu, C., Angus, P. (2004). Clinical emergence of entecavirresistant hepatitis B virus requires additional substitutions in virus already resistant to lamivudine. Antimicrobial Agents and Chemotherapy, 48 , 3498.
171. Chang, T., Gish, R., Hadziyannis, S., Cianciara, J., Rizzetto, M., Schiff, E., Pastore, G., Bacon, B., Poynard, T., Joshi, S. (2005). A dose-ranging study of the efficacy and tolerability of entecavir in lamivudine-refractory chronic hepatitis B patients. Gastroenterology, 129 , 1198-1209.
172. De Man, R. A., Wolters, L. M. M., Nevens, F., Chua, D., Sherman, M., Lai, C. L., Gadano, A., Lee, Y., Mazzotta, F., Thomas, N., DeHertogh, D. (2001). Safety and efficacy of oral entecavir given for 28 days in patients with chronic hepatitis B virus infection. Hepatology, 34 , 578-582.
173. Lai, C. L., Rosmawati, M., Lao, J., Van Vlierberghe, H., Anderson, F. H., Thomas, N., Dehertogh, D. (2002). Entecavir is superior to lamivudine in reducing hepatitis B virus DNA in patients with chronic hepatitis B infection. Gastroenterology, 123 , 1831-1838.
174. Yao, G., Xu, D., Wang, B., Zhou, X., Lei, B., Zhang, D. (2003). A phase II study in China of the safety and antiviral activity of entecavir in adults with chronic hepatitis B infection. Hepatology, 38 , 711A.
175. Guo, J.-J., Li, Q.-L., Shi, X.-F., Zhang, D.-Z., Zeng, A.-Z., Feng, T., Huang, A.-L. (2009). Dynamics of hepatitis B virus resistance to entecavir in a nucleoside/nucleotide-näive patient. Antiviral Research, 81 , 180-183.
176. Ziegler, F. E., Sarpong, M. A. (2003). Radical cyclization studies directed toward the synthesis of BMS-200475 'entecavir': The carbocyclic core. Tetrahedron, 59 , 9013-9018.
177. Roy, B., Deslongchamps, P. (1985). Synthesis and resolution of r (-) -5-hexyn-3-ol. Canadian Journal of Chemistry, 63 , 651-654.
178. Ohira, S. (1989). Methanolysis of dimethyl (1-diazo-2-oxopropyl) phosphonate: Generation of dimethyl (diazomethyl) phosphonate and reaction with carbonyl compounds. Synthetic Communications, 19 , 561-564.
179. Sharon, A., Chu, C. K. (2008). Understanding the molecular basis of HBV drug resistance by molecular modeling. Antiviral Research, 80 , 339-353.
180. Ruediger, E., Martel, A., Meanwell, N., Solomon, C., Turmel, B. (2004). Novel 3'-deoxy analogs of the anti-HBV agent entecavir: Synthesis of enantiomers from a single chiral epoxide. Tetrahedron Letters, 45 , 739-742.
181. Wang, J., Singh, U. S., Yoo, J., Joo, J. E., Chavre, S., Huang, Z., Murray, M., Korba, B., Chu, C. K. (2010). A novel ant-HBV carbocyclic nucleoside active against wildtype and drug resistant hepatitis B virus (HBV) mutants. International Roundtable on Nucleosides, Nucleotides and Nucleic Acids, IRT 2010, Lyon, France, PA041 , 148-149.
182. Vince, R., Daluge, S. (1977). Carbocyclic arabinosyladenine, an adenosine deaminase resistant antiviral agent. Journal of Medicinal Chemistry, 20 , 612-613.
183. De Clercq, E., Descamps, J., De Somer, P., Barr, P., Jones, A., Walker, R. (1979). (E)-5-(2-bromovinyl)-2'-deoxyuridine: A potent and selective anti-herpes agent. Proceedings of the National Academy of Sciences of the United States of America, 76 , 2947-2951.
184. Desgranges, C., Razaka, G., Bricaud, H., De Clercq, E. (1985). Inhibition and reversal of degradation of the antiviral drug.(E)-5-(2-bromovinyl)-2'-deoxyridine in oiwo. Biochemical Pharmacology, 34 , 405-406.
185. Herdewijn, P., Clercq, E. D., Balzarini, J., Vanderhaeghe, H. (1985). Synthesis and antiviral activity of the carbocyclic analogues of (E)-5-(2-halovinyl)-2'-deoxyuridines and (E)-5-(2-halovinyl)-2'-deoxycytidines. Journal of Medicinal Chemistry, 28 , 550-555.
186. Wyatt, P., Anslow, A., Coomber, B., Cousins, R., Evans, D., Gilbert, V., Humber, D., Paternoster, I., Sollis, S., Tapolczay, D. (1995). A short high yielding synthesis of the potent anti-VZV carbocyclic nucleoside analogue carba-BVDU. Nucleosides, Nucleotides and Nucleic Acids, 14 , 2039-2049.
187. Shealy, Y. F., O'Dell, C. A., Shannon, W. M., Arnett, G. (1984). Synthesis and antiviral activity of carbocyclic analogs of 2'-deoxyribofuranosides of 2-amino-6-substituted-purines and of 2-amino-6-substituted-8-azapurines. Journal of Medicinal Chemistry, 27 , 1416-1421.
188. Price, P., Banerjee, R., Acs, G. (1989). Inhibition of the replication of hepatitis B virus by the carbocyclic analogue of 2'-deoxyguanosine. Proceedings of the National Academy of Sciences, 86 , 8541-8544.
189. Lee Bennett Jr., L., Fulmer Shealy, Y., Allan, P. W., Rose, L. M., Shannon, W. M., Arnett, G. (1990). Phosphorylation of the carbocyclic analog of 2'-deoxyguanosine in cells infected with herpes viruses. Biochemical Pharmacology, 40 , 1515-1522.
190. Lang, H., Moser, H. (1994). An efficient total synthesis of carbocyclic 2'-deoxyribonucleosides. Helvetica Chimica Acta, 77 , 1527-1540.
191. Borthwick, A. D., Crame, A. J., Exall, A. M., Weingarten, G. G., Mahmoudian, M. (1995). A short, convergent synthesis of two chiral antiviral agents, (+) carbocyclic 2'-deoxy-5-[(E)-2-bromovinyl] uridine and (+) carbocyclic 2'-deoxyguanosine. Tetrahedron Letters, 36 , 6929-6932.
192. Choo, H., Chong, Y., Chu, C. K. (2001). Solid phase synthesis of carbocyclic l-2'-deoxynucleosides. Organic Letters, 3 , 1471-1473.
193. Biggadike, K., Borthwick, A., Exall, A., Kirk, B., Ward, R. (1988). 2 -deoxy-2'-fluoro-ara-aristeromycin, a new anti-herpes agent: The first direct introduction of a 2'-fluoro substituent into a carbocyclic nucleoside. Journal of the Chemical Society, Chemical Communications, 1988 , 898-900.
194. Borthwick, A. D., Kirk, B. E., Biggadike, K., Exall, A. M., Butt, S., Roberts, S. M., Knight, D. J., Coates, J. A. V., Ryan, D. M. (1991). Fluorocarbocyclic nucleosides: Synthesis and antiviral activity of 2'-and 6'-fluorocarbocyclic 2'-deoxyguanosines. Journal of Medicinal Chemistry, 34 , 907-914.
195. Borthwick, A. D., Evans, D. N., Kirk, B. E., Biggadike, K., Exall, A. M., Youds, P., Roberts, S. M., Knight, D. J., Coates, J. A. V. (1990). Fluoro carbocyclic nucleosides: Synthesis and antiviral activity of 2'-and 6'-fluoro carbocyclic pyrimidine nucleosides including carbocyclic 1-(2-deoxy-2-fluoro-β-d-arabinofuranosyl)-5-methyluracil and carbocyclic 1-(2-deoxy-2-fluoro-β-d-arabinofuranosyl)-5-iodouracil. Journal of Medicinal Chemistry, 33 , 179-186.
196. Biggadike, K., Borthwick, A., Evans, D., Exall, A., Kirk, B., Roberts, S., Stephenson, L., Youds, P. (1988). Use of diethylaminosulphur trifluoride (DAST) in the preparation of synthons of carbocyclic nucleosides. Journal of the Chemical Society, Perkin Transactions 1 , 1988 , 549-554.
197. Liu, L. J., Kim, S. W., Lee, W., Hong, J. H. (2009). Selective ring-opening fluorination of epoxide: An efficient synthesis of 2'-C-fluoro-2'-C-methyl carbocyclic nucleosides. Bulletin of the Korean Chemical Society, 30 , 2989-2992.
198. Boyer, P. L., Vu, B. C., Ambrose, Z., Julias, J. G., Warnecke, S., Liao, C., Meier, C., Marquez, V. E., Hughes, S. H. (2009). The nucleoside analogue D-carba T blocks HIV-1 reverse transcription. Journal of Medicinal Chemistry, 52 , 5356-5364.
199. Jessel, S., Hense, E., Meier, C. (2007). Cyclopentane-nucleobase coupling in the synthesis of carbocyclic L-nucleosides: Is a Sn2-reaction an alternative to the mitsunobu-reaction? Nucleosides, Nucleotides & Nucleic Acids, 26 , 1181-1184.
200. Migliore, M. D., Zonta, N., McGuigan, C., Henson, G., Andrei, G., Snoeck, R., Balzarini, J. (2007). Synthesis and antiviral activity of the carbocyclic analogue of the highly potent and selective anti-VZV bicyclo furano pyrimidines. Journal of Medicinal Chemistry, 50 , 6485-6492.
201. Mueller, H., Hopfinger, M., Carell, T. (2008). Synthesis of a stabilized version of the imidazolone DNA lesion. ChemBioChem, 9 , 1617-1622.
202. Isono, K. (1988). Nucleoside antibiotics: Structure, biological activity, and biosynthesis. The Journal of Antibiotics, 41 , 1711-1739.
203. Kinoshita, K., Yaginuma, S., Hayashi, M., Nakatsu, K. (1985). The structure of neplanocin C. Nucleosides, Nucleotides and Nucleic Acids, 4 , 661-668.
204. Rodriguez, J. B., Marquez, V. E., Nicklaus, M. C., Barchi, J. J. (1993). Synthesis of cyclopropane-fused dideoxycarbocyclic nucleosides structurally related to neplanocin C. Tetrahedron Letters, 34 , 6233-6236.
205. Rodriguez, J. B., Marquez, V. E., Nicklaus, M. C., Mitsuya, H., Barchi, J. J. (1994). Conformationally locked nucleoside analogs. Synthesis of dideoxycarbocyclic nucleoside analogs structurally related to neplanocin C. Journal of Medicinal Chemistry, 37 , 3389-3399.
206. Altmann, K.-H., Kesselring, R., Francotte, E., Rihs, G. (1994). 4',6'-methano carbocyclic thymidine: A conformationally constrained building block for oligonucleotides. Tetrahedron Letters, 35 , 2331-2334.
207. Staroscik, J. A., Rickborn, B. (1972). Conformational aspects of the directive effect of the homoallylic hydroxyl group in the simmons-smith reaction. The Journal of Organic Chemistry, 37 , 738-740.
208. Siddiqui, M., Ford, H., George, C., Marquez, V. (1996). Synthesis, conformational analysis, and biological activity of a rigid carbocyclic analogue of 2 -deoxy aristeromycin built on a bicyclo [3.1. 0] hexane template. Nucleosides, Nucleotides and Nucleic Acids, 15 , 235-250.
209. Marquez, V. E., Siddiqui, M. A., Ezzitouni, A., Russ, P., Wang, J., Wagner, R. W., Matteucci, M. D. (1996). Nucleosides with a twist. Can fixed forms of sugar ring pucker influence biological activity in nucleosides and oligonucleotides? Journal of Medicinal Chemistry, 39 , 3739-3747.
210. Boyer, P. L., Julias, J. G., Marquez, V. E., Hughes, S. H. (2005). Fixed conformation nucleoside analogs effectively inhibit excision-proficient HIV-1 reverse transcriptases. Journal of Molecular Biology, 345 , 441-450.
211. Comin, M. J., Agbaria, R., Ben-Kasus, T., Huleihel, M., Liao, C., Sun, G., Nicklaus, M. C., Deschamps, J. R., Parrish, D. A., Marquez, V. E. (2007). Sculpting the bicyclo[3.1.0]hexane template of carbocyclic nucleosides to improve recognition by herpes thymidine kinase. Journal of the American Chemical Society, 129 , 6216-6222.
212. Marquez, V. E., Ben-Kasus, T., Barchi, J. J., Green, K. M., Nicklaus, M. C., Agbaria, R. (2004). Experimental and structural evidence that herpes 1 kinase and cellular DNA polymerase(s) discriminate on the basis of sugar pucker. Journal of the American Chemical Society, 126 , 543-549.
213. Marquez, V. E., Choi, Y., Comin, M. J., Russ, P., George, C., Huleihel, M., Ben-Kasus, T., Agbaria, R. (2005). Understanding how the herpes thymidine kinase orchestrates optimal sugar and nucleobase conformations to accommodate its substrate at the active site: A chemical approach. Journal of the American Chemical Society, 127 , 15145-15150.
214. Marquez, V. E., Ezzitouni, A., Russ, P., Siddiqui, M. A., Ford, H., Feldman, R. J., Mitsuya, H., George, C., Barchi, J. J. (1998). HIV-1 reverse transcriptase can discriminate between two conformationally locked carbocyclic AZT triphosphate analogues. Journal of the American Chemical Society, 120 , 2780-2789.
215. Russ, P. L., Gonzalez-Moa, M. J., Vu, B. C., Sigano, D. M., Kelley, J. A., Lai, C. C., Deschamps, J. R., Hughes, S. H., Marquez, V. E. (2009). North-and southbicyclo[ 3.1.0]hexene nucleosides: The effect of ring planarity on anti-HIV activity. ChemMedChem, 4 , 1354-1363.
216. Jeong, L. S., Lee, J. A., Kim, H. O., Tosh, D. K., Moon, H. R., Lee, S.-J., Lee, K. M., Sheen, Y. Y., Chun, M. W. (2007). Asymmetric synthesis of cyclopropyl-fused 2'-C-methylcarbanucleosides as potential anti-HCV agents. Nucleosides, Nucleotides & Nucleic Acids, 26 , 1021-1024.
217. Sála, M., De Palma, A. M., Hrebabecký, H., Nencka, R., Dracínský, M., Leyssen, P., Neyts, J., Holý, A. (2010). Design, synthesis, and biological evaluation of novel coxsackievirus B3 inhibitors. Bioorganic & Medicinal Chemistry, 18 , 4374-4384.
218. Sála, M., Hrebabecký, H., Dracínský, M., Masojídková, M., De Palma, A. M., Neyts, J., Holý, A. (2009). Norbornane as the novel pseudoglycone moiety in nucleosides. Tetrahedron, 65 , 9291-9299.
219. Quadrelli, P., Mella, M., Carosso, S., Bovio, B., Caramella, P. (2007). A straightforward synthesis of isoxazoline-based carbocyclic nucleosides from 1,3-cyclohexadiene through nitrosocarbonyl chemistry. European Journal of Organic Chemistry, 6003-6015.
220. Quadrelli, P., Piccanello, A., Mella, M., Corsaro, A., Pistarà, V. (2008). From cyclopentadiene to isoxazoline-carbocyclic nucleosides: A rapid access to biological molecules through aza-diels-alder reactions. Tetrahedron, 64 , 3541-3547.
221. Zhao, Y., Yang, T., Lee, M., Lee, D., Newton, M. G., Chu, C. K. (1995). Asymmetric synthesis of (1'S,2'R)-cyclopropyl carbocyclic nucleosides. The Journal of Organic Chemistry, 60 , 5236-5242.
222. Ashton, W. T., Meurer, L. C., Cantone, C. L., Field, A. K., Hannah, J., Karkas, J. D., Liou, R., Patel, G. F., Perry, H. C. (1988). Synthesis and antiherpetic activity of (+/-) -9-[[(Z)-2-(hydroxymethyl)cyclopropyl]methyl]guanine and related compounds. Journal of Medicinal Chemistry, 31 , 2304-2315.
223. Sekiyama, T., Hatsuya, S., Tanaka, Y., Uchiyama, M., Ono, N., Iwayama, S., Oikawa, M., Suzuki, K., Okunishi, M., Tsuji, T. (1998). Synthesis and antiviral activity of novel acyclic nucleosides: Discovery of a cyclopropyl nucleoside with potent inhibitory activity against herpesviruses. Journal of Medicinal Chemistry, 41 , 1284-1298.
224. Iwayama, S., Ono, N., Ohmura, Y., Suzuki, K., Aoki, M., Nakazawa, H., Oikawa, M., Kato, T., Okunishi, M., Nishiyama, Y. (1998). Antiherpesvirus activities of (1'S, 2'R)-9-{[1', 2'-bis (hydroxymethyl) cycloprop-1'-yl] methyl} guanine (A-5021) in cell culture. Antimicrobial Agents and Chemotherapy, 42 , 1666-1670.
225. Onishi, T., Mukai, C., Nakagawa, R., Sekiyama, T., Aoki, M., Suzuki, K., Nakazawa, H., Ono, N., Ohmura, Y., Iwayama, S., Okunishi, M., Tsuji, T. (1999). Synthesis and antiviral activity of novel anti-VZV 5-substituted uracil nucleosides with a cyclopropane sugar moiety. Journal of Medicinal Chemistry, 43 , 278-282.
226. Qiu, Y.-L., Hempel, A., Camerman, N., Camerman, A., Geiser, F., Ptak, R. G., Breitenbach, J. M., Kira, T., Li, L., Gullen, E., Cheng, Y.-C., Drach, J. C., Zemlicka, J. (1998). (R)-(-)-and (S)-(+)-synadenol: Synthesis, absolute configuration, and enantioselectivity of antiviral effect. Journal of Medicinal Chemistry, 41 , 5257-5264.
227. Qiu, Y.-L., Ksebati, M. B., Ptak, R. G., Fan, B. Y., Breitenbach, J. M., Lin, J.-S., Cheng, Y.-C., Kern, E. R., Drach, J. C., Zemlicka, J. (1998). (Z)-and (E)-2-((hydroxymethyl)cyclopropylidene)methyladenine and -guanine. New nucleoside analogues with a broad-spectrum antiviral activity. Journal of Medicinal Chemistry, 41 , 10-23.
228. Guan, H.-P., Ksebati, M. B., Cheng, Y.-C., Drach, J. C., Kern, E. R., Zemlicka, J. (2000). Spiropentane mimics of nucleosides: Analogues of 2'-deoxyadenosine and 2'-deoxyguanosine. Synthesis of all stereoisomers, isomeric assignment, and biological activity. The Journal of Organic Chemistry, 65 , 1280-1290.
229. Zhou, S., Drach, J. C., Prichard, M. N., Zemlicka, J. (2009). (Z)-and (E)-2-(1,2-dihydroxyethyl)methylenecyclopropane analogues of 2'-deoxyadenosine and 2'-deoxyguanosine. Synthesis of all stereoisomers, absolute configuration, and antiviral activity. Journal of Medicinal Chemistry, 52 , 3397-3407.
230. Nakamura, H., Hasegawa, S., Shimada, N., Fujii, A., Takita, T., Iitaka, Y. (1986). The x-ray structure determination of oxetanocin. The Journal of Antibiotics, 39 , 1626-1629.
231. Shimada, N., Hasegawa, S., Harada, T., Tomisawa, T., Fujii, A., Takita, T. (1986). Oxetanocin, a novel nucleoside from bacteria. The Journal of Antibiotics, 39 , 1623-1625.
232. Hoshino, H., Shimizu, N., Shimada, N., Takita, T., Takeuchi, T. (1987). Inhibition of infectivity of human immunodeficiency virus by oxetanocin. The Journal of Antibiotics, 40 , 1077-1078.
233. Honjo, M., Maruyama, T., Sato, H., Horii, T. (1989). Synthesis of the carbocyclic analogue of oxetanocin A. Chemical & Pharmaceutical Bulletin, 37 , 1413-1415.
234. Ichikawa, Y., Narita, A., Shiozawa, A., Hayashi, Y., Narasaka, K. (1989). Enantioand diastereo-selective synthesis of carbocyclic oxetanocin analogues. Journal of the Chemical Society, Chemical Communications, 1989 , 1919-1921.
235. Hayashi, S., Norbeck, D., Rosenbrook, W., Fine, R., Matsukura, M., Plattner, J., Broder, S., Mitsuya, H. (1990). Cyclobut-a and cyclobut-g, carbocyclic oxetanocin analogs that inhibit the replication of human immunodeficiency virus in t cells and monocytes and macrophages in vitro. Antimicrobial Agents and Chemotherapy, 34 , 287-294.
236. Tenney, D., Yamanaka, G., Voss, S., Cianci, C., Tuomari, A., Sheaffer, A., Alam, M., Colonno, R. (1997). Lobucavir is phosphorylated in human cytomegalovirusinfected and-uninfected cells and inhibits the viral DNA polymerase. Antimicrobial Agents and Chemotherapy, 41 , 2680-2685.
237. Maruyama, T., Hanai, Y., Sato, Y., Snoeck, R., Andrei, G., Hosoya, M., Balzarini, J., De Clercq, E. (1993). Synthesis and antiviral activity of carbocyclic oxetanocin analogues (C-OXT-A, C-OXT-G) and related compounds. Chemical & Pharmaceutical Bulletin, 41 , 516-521.
238. Ahmad, S., Bisacchi, G. S., Field, A. K., Jacobs, G. A., Tuomari, A. V., McGeever-Rubin, B., Vite, G. D., Zahler, R. (1993). Optically active fluorinated cyclobutane nucleoside analogs with potent anti-herpes activity. Bioorganic & Medicinal Chemistry Letters, 3 , 1215-1218.
239. Vite, G. D., Tino, J. A., Zahler, R., Goodfellow, V., Tuomari, A. V., McGeever-Rubin, B., Field, A. K. (1993). Differences in antiviral activities for isomers of a fluorinated cyclobutane nucleoside analog. Bioorganic & Medicinal Chemistry Letters, 3 , 1211-1214.
240. Wu, J., Schneller, S. W., Seley, K. L., Snoeck, R., Andrei, G., Balzarini, J., De Clercq, E. (1997). Carbocyclic oxetanocins lacking the C-3' methylene. Journal of Medicinal Chemistry, 40 , 1401-1406.
241. Li, Y., Mao, S., Hager, M. W., Becnel, K. D., Schinazi, R. F., Liotta, D. C. (2007). Synthesis and evaluation of 2'-substituted cyclobutyl nucleosides and nucleotides as potential anti-HIV agents. Bioorganic & Medicinal Chemistry Letters, 17 , 3398-3401.
242. Bondada, L., Gumina, G., Nair, R., Ning, X. H., Schinazi, R. F., Chu, C. K. (2004). Synthesis of novel spiro [2,3] hexane carbocyclic nucleosides via enzymatic resolution. Organic Letters, 6 , 2531-2534.
243. Koga, M., Wilk, A., Moore, M. F., Scremin, C. L., Zhou, L., Beaucage, S. L. (1995). Synthesis and physicochemical properties of alternating. alpha.,.beta.-oligodeoxyribonucleotides with alternating (3'.fwdarw.3')-and (5'.fwdarw.5')-internucleotidic phosphodiester linkages. The Journal of Organic Chemistry, 60 , 1520-1530.
244. Mansour, T. S., Jin, H., Wang, W., Hooker, E. U., Ashman, C., Cammack, N., Salomon, H., Belmonte, A. R., Wainberg, M. A. (1995). Anti-human immunodeficiency virus and anti-hepatitis-B virus activities and toxicities of the enantiomers of 2'-deoxy-3'-oxa-4'-thiocytidine and their 5-fluoro analogs in vitro. Journal of Medicinal Chemistry, 38, 1-4.
245. Wang, J., Busson, R., Blaton, N., Rozenski, J., Herdewijn, P. (1998). Enantioselective approach to the synthesis of cyclohexane carbocyclic nucleosides. The Journal of Organic Chemistry, 63 , 3051-3058.
246. Wang, J., Froeyen, M., Hendrix, C., Andrei, G., Snoeck, R., De Clercq, E., Herdewijn, P. (2000). The cyclohexene ring system as a furanose mimic: Synthesis and antiviral activity of both enantiomers of cyclohexenylguanine. Journal of Medicinal Chemistry, 43 , 736-745.
247. Ferrer, E., Alibes, R., Busque, F., Figueredo, M., Font, J., de March, P. (2009). Enantio-divergent synthesis of cyclohexenyl nucleosides. Journal of Organic Chemistry, 74 , 2425-2432.