Design, synthesis, and biological evaluation of new 2′-deoxy- 2′-fluoro-4′-triazole cytidine nucleosides as potent antiviral agents

European Journal of Medicinal Chemistry

Volumn 63, Issue , 2013, Pages 739-745

  Wu, Jie ^a   Yu, Wenquan ^a   Fu, Leixia ^a   He, Wu ^a   Wang, Yao ^a   Chai, Baoshan ^a   Song, Chuanjun ^a   Chang, Junbiao ^a  

^a ZHENGZHOU UNIVERSITY   (China)

Author keywords

2 Deoxy 2 fluoro 4 triazole nucleosides; Anti HBV activity; Anti HIV activity; Nucleoside reverse transcriptase inhibitor (NRTI)

Indexed keywords

1 ( 4' AZIDO 2' DEOXY 2' FLUORO ARABINOFURANOSYL)CYTOSINE; 1 [ 4' ( 1,2,3 TRIAZOL 1 YL) 2' DEOXY 2' FLUORO ARABINOFURANOSYL]CYTOSINE; 1 [ 4' ( 4 BUTYL 1,2,3 TRIAZOL 1 YL) 2' DEOXY 2 ' FLUORO ARABINOFURANOSYL]CYTOSINE; 1 [ 4' ( 4 CYTOHEXYLMETHYL 1,2,3 TRIAZOL 1 YL) 2' DEOXY 2' FLUORO ARABINOFURANOSYL]CYTOSINE; 1 [ 4' ( 4 ETHYLPHENYL 1,2,3 TRIAZOL 1 YL) 2' DEOXY 2' FLUORO ARABINOFURANOSYL]CYTOSINE; 1 [ 4' ( 4 HYDROXYCYCLOPENTYL 1,2,3 TRIAZOL 1 YL) 2' DEOXY 2' FLUORO ARABINOFURANOSYL]CYTOSINE; 1 [ 4' ( 4 METHYLPHENYL 1,2,3 TRIAZOL 1 YL) 2' DEOXY 2' FLUORO ARABINOFURANOSYL]CYTOSINE; 1 [ 4' ( 4 PHENYL 1,2,3 TRIAZOL 1 YL) 2' DEOXY 2' FLUORO ARABINOFURANOSYL]CYTOSINE; 1 [ 4' ( 4 TERT BUTYL 1,2,3 TRIAZOL 1 YL) 2' DEOXY 2 FLUORO ARABINOFURANOSYL]CYTOSINE; 1 [ 4' (CYCLOPROPYL 1,2,3 TRIAZOL 1 YL) 2' DEOXY 2' FLUORO ARABINOFURANOSYL]CYTIDINE; ALKYNE DERIVATIVE; ANTIRETROVIRUS AGENT; CUPROUS ION; CYTIDINE DERIVATIVE; CYTOSINE DERIVATIVE; NUCLEOSIDE DERIVATIVE; RNA DIRECTED DNA POLYMERASE INHIBITOR; UNCLASSIFIED DRUG; ZIDOVUDINE;

ANTIVIRAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CELL SURVIVAL; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYCLOADDITION; CYTOTOXICITY; DRUG DESIGN; DRUG POTENCY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; VIRUS STRAIN;

ANTIVIRAL AGENTS; CELL SURVIVAL; CYTIDINE; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; ENZYME-LINKED IMMUNOSORBENT ASSAY; HEK293 CELLS; HEP G2 CELLS; HEPATITIS B E ANTIGENS; HEPATITIS B SURFACE ANTIGENS; HEPATITIS B VIRUS; HIV-1; HUMANS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; TRIAZOLES;

EID: 84875933666     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.02.042     Document Type: Article

References (65)

1. N. Shulman, and M. Winters A review of HIV-1 resistance to the nucleoside and nucleotide inhibitors Curr. Drug Targets Infect. Disord. 3 2003 273 281
2. W. Lewis, B.J. Day, and W.C. Copeland Mitochondrial toxicity of NRTI antiviral drugs: an integrated cellular perspective Nat. Rev. Drug Discov. 2 2003 812 822
3. J. Martinez-Picado, M.P. De Pasquale, N. Kartsonis, G.J. Hanna, J. Wong, D. Finzi, E. Rosenberg, H.F. Gunthard, L. Sutton, A. Savara, C.J. Petropoulos, N. Hellmann, B.D. Walker, D.D. Richman, R. Siliciano, and R.T. D'Aquila Antiretroviral resistance during successful therapy of HIV type 1 infection Proc. Natl. Acad. Sci. U. S. A. 97 2000 10948 10953
4. S.J. Little, S. Holte, J.P. Routy, E.S. Daar, M. Markowitz, A.C. Collier, R.A. Koup, J.W. Mellors, E. Connick, B. Conway, M. Kilby, L. Wang, J.M. Whitcomb, N.S. Hellmann, and D.D. Richman Antiretroviral-drug resistance among patients recently infected with HIV N. Engl. J. Med. 347 2002 385 394
5. G. Romeo, U. Chiacchio, A. Corsaro, and P. Merino Chemical synthesis of heterocyclic-sugar nucleoside analogues Chem. Rev. 110 2010 3337
6. C. Perigaud, G. Gosselin, and J.-L. Imbach Nucleoside analogues as chemotherapeutic agents: a review Nucleosides Nucleotides 11 1992 903 945
7. C.R. Wagner, V.V. Iyer, and E. McIntee Pronucleotides: toward the in vivo delivery of antiviral and anticancer nucleotides J. Med. Res. Rev. 20 2000 417 451
8. G.J. Koomen Synthesis and biological properties of selected nucleoside analogues Recl. Trav. Chim. Pays-Bas 112 1993 51 65
9. X. Tan, C.K. Chu, and F.D. Boudinot Development and optimization of anti-HIV nucleoside analogs and prodrugs: a review of their cellular pharmacology, structure-activity relationships and pharmacokinetics Adv. Drug Deliv. Rev. 39 1999 117 151
10. D.M. Huryn, and M. Okabe AIDS-driven nucleoside chemistry Chem. Rev. 92 1992 1745 1768
11. C.K. Chu, and S.J. Cutler Chemistry and antiviral activities of acyclonucleosides J. Heterocycl. Chem. 23 1986 289 319
12. H. Gao, and A.K. Mitra Synthesis of acyclovir, ganciclovir and their prodrugs: a review Synthesis 2000 329 351
13. A. Holy Phosphonomethoxyalkyl analogs of nucleotides Curr. Pharm. Des. 9 2003 2567 2592
14. A. Mieczkowski, V. Roy, and L.A. Agrofoglio Preparation of cyclonucleosides Chem. Rev. 110 2010 1828 1856
15. L.W. Hertel, J.S. Kroin, J.W. Misner, and J.M. Tustin Synthesis of 2-deoxy-2,2-difluoro-d-ribose and 2-deoxy-2,2′-difluoro-d-ribofuranosyl nucleosides J. Org. Chem. 53 1988 2406 2409
16. V.E. Marquez, C.K.-H. Tseng, H. Mitsuya, S. Aoki, J.A. Kelley, H. Ford Jr., and J.S. Driscoll Acid-stable 2′-fluoro purine dideoxynucleosides as active agents against HIV J. Med. Chem. 33 1990 978 985
17. B.K. Chun, R.F. Schinazi, Y.-C. Cheng, and C.K. Chu Synthesis of 2′,3′-dideoxy-3′-fluoro-l-ribonucleosides as potential antiviral agents from d-sorbitol Carbohydr. Res. 328 2000 49 59
18. K. Klumpp, G. Kalayanov, H. Ma, S.L. Pogam, V. Leveque, W.R. Jiang, N. Inocencio, A.D. Witte, S. Rajyaguru, E. Tai, S. Chanda, M.R. Irwin, C. Sund, A. Winqist, T. Maltseva, S. Eriksson, E. Usova, M. Smith, A. Alker, I. Najera, N. Cammack, J.A. Martin, N.G. Johansson, and D.B. Smith 2′-Deoxy-4′- azido nucleoside analogs are highly potent inhibitors of hepatitis C virus replication despite the lack of 2′-α-hydroxyl groups J. Biol. Chem. 283 2008 2167 2175
19. H. Mitsuya, K.J. Weinhold, P.A. Furman, M.H. St Clair, S.N. Lehrman, R.C. Gallo, D. Bolognesi, D.W. Barry, and S. Broder 3′-Azido-3′- deoxythymidine (BW A509U): an antiviral agent that inhibits the infectivity and cytopathic effect of human T-lymphotropic virus type III/lymphadenopathy- associated virus in vitro Proc. Natl. Acad. Sci. U. S. A. 82 1985 7096 7100
20. M. Yokoyama Synthesis and biological activity of thionucleosides Synthesis 2000 1637 1655
21. P. Merino Heterocyclic nucleosides: chemical synthesis and biological properties Curr. Med. Chem. 13 2006 539 545
22. P. Merino, T. Tejero, and I. Delso Current developments in the synthesis and biological activity of aza-C-nucleosides: immucillins and related compounds Curr. Med. Chem. 15 2008 954 967
23. U. Hacksell, and G.D. Daves Jr. The chemistry and biochemistry of C-nucleosides and C-arylglycosides Prog. Med. Chem. 22 1985 1 65
24. M.A.E. Shaban, and A.Z. Nasr The chemistry of C-nucleosides and their analogs I: C-nucleosides of hetero monocyclic bases Adv. Heterocycl. Chem. 68 1997 223 432
25. M.A.E. Shaban The chemistry of C-nucleosides and their analogs II: C-nucleosides of condensed heterocyclic bases Adv. Heterocycl. Chem. 70 1997 163 337
26. Q. Wang, X. Liu, Q. Wang, Y. Zhang, J. Jiang, X. Guo, Q. Fan, L. Zheng, X. Yu, N. Wang, Z. Pan, C. Song, W. Qi, and J. Chang FNC, a novel nucleoside analogue inhibits cell proliferation and tumor growth in a variety of human cancer cells Biochem. Pharmacol. 81 2011 848 855
27. Q. Wang, W. Hu, S. Wang, Z. Pan, L. Tao, X. Guo, K. Qian, C. Chen, K. Lee, and J. Chang Synthesis of new 2′-deoxy-2′-fluoro-4′-azido nucleoside analogues as potent anti-HIV agents Eur. J. Med. Chem. 46 2011 4178 4183
28. Q. Wang, Y. Li, C. Song, K. Qian, C. Chen, K. Lee, and J. Chang Synthesis and anti-HIV activity of 2′-deoxy-2′-fluoro-4′-C-ethynyl nucleoside analogs Bioorg. Med. Chem. Lett. 20 2010 4053 4056
29. X. Guo, Y. Li, L. Tao, Q. Wang, S. Wang, W. Hu, Z. Pan, Q. Yang, Y. Cui, Z. Ge, L. Dong, X. Yu, H. An, C. Song, and J. Chang Synthesis and anti-HIV-1 activity of 4-substituted-7-(2′-deoxy-2′-fluoro-4′-azido- β-d-ribofuranosyl)pyrrolo[2,3-d]pyrimidine analogues Bioorg. Med. Chem. Lett. 21 2011 6770 6772
30. K.A. Watanabe, U. Reichman, K. Hirota, C. Lopez, and J.J. Fox Nucleosides. 110. Synthesis and antiherpes virus activity of some 2′-fluoro-2′-deoxyarabinofuranosylpyrimidine nucleosides J. Med. Chem. 22 1979 21 24
31. O.D. Schaerer, and G.L. Verdine A designed inhibitor of base-excision DNA repair J. Am. Chem. Soc. 117 1995 10781 10782
32. S.G. Agalave, S.R. Maujan, and V.S. Pore Click chemistry: 1,2,3-triazoles as pharmacophores Chem. - Asian J. 6 2011 2696 2718
33. A. Brik, J. Alexandratos, Y. Lin, J.H. Elder, A.J. Olson, A. Wlodawer, D.S. Goodsell, and C. Wong 1,2,3-Triazole as a peptide surrogate in the rapid synthesis of HIV-1 protease inhibitors ChemBioChem 6 2005 1167 1169
34. M. Meldal, and C.W. Tornøe Cu-catalyzed azide-alkyne cycloaddition Chem. Rev. 108 2008 2952 3015
35. F. Amblard, J.H. Cho, and R.F. Schinazi Cu(I)-catalyzed Huisgen azide-alkyne 1,3-dipolar cycloaddition reaction in nucleoside, nucleotide, and oligonucleotide chemistry Chem. Rev. 109 2009 4207 4220
36. T.S. Seo, Z. Li, H. Ruparel, and J. Ju Click chemistry to construct fluorescent oligonucleotides for DNA sequencing J. Org. Chem. 68 2003 609 612
37. L.V. Lee, M.L. Mitchell, S.J. Huang, V.V. Fokin, K.B. Sharpless, and C.H. Wong A potent and highly selective inhibitor of human alpha-1,3- fucosyltransferase via click chemistry J. Am. Chem. Soc. 125 2003 9588 9589
38. J. Gierlich, G.A. Burley, P.M.E. Gramlich, D.M. Hammond, and T. Carell Click chemistry as a reliable method for the high-density postsynthetic functionalization of alkyne-modified DNA Org. Lett. 8 2006 3639 3642
39. I. Kosiova, S. Kovackova, and P. Kois Synthesis of coumarin-nucleoside conjugates via Huisgen 1,3-dipolar cycloaddition Tetrahedron 63 2007 312 320
40. F. Seela, and V.R. Sirivolu Nucleosides and oligonucleotides with diynyl side chains: base pairing and functionalization of 2′-deoxyuridine derivatives by the copper(I)-catalyzed alkyne-azide 'click' cycloaddition Helv. Chim. Acta 90 2007 535 552
41. A. Jatsch, A. Kopyshev, E. Mena-Osteritz, and P. Baeuerle Self-organizing oligothiophene-nucleoside conjugates: versatile synthesis via "click"-chemistry Org. Lett. 10 2008 961 964
42. L. Cosyn, K.K. Palaniappan, S.-K. Kim, H.T. Duong, Z.G. Gao, K.A. Jacobson, and S. Van Calenbergh 2-Triazole-substituted adenosines: a new class of selective A3 adenosine receptor agonists, partial agonists, and antagonists J. Med. Chem. 49 2006 7373 7383
43. Y. Xia, W. Li, F. Qu, Z. Fan, X. Liu, C. Berro, E. Rauzy, and L. Peng Synthesis of bitriazolyl nucleosides and unexpectedly different reactivity of azidotriazole nucleoside isomers in the Huisgen reaction Org. Biomol. Chem. 5 2007 1695 1701
44. L. Li, B. Lin, Z. Yang, L. Zhang, and L. Zhang A concise route for the preparation of nucleobase-simplified cADPR mimics by click chemistry Tetrahedron Lett. 49 2008 4491 4493
45. M. Tourirte, T. Oulih, H.B. Lazrek, J.L. Barascut, J.L. Imbach, and N.A. Almasoudi Synthesis of 3′-deoxy-3′-[4-(pyrimidin-1-yl)methyl-1,2,3- triazol-1-yl]thymidine via 1,3-dipolar cycloaddition Nucleosides, Nucleotides and Nucleic Acids 22 2003 1985 1993
46. H. Skarpos, S.N. Osipov, D.V. Vorob'eva, I.L. Odinets, E. Lork, and G.-V. Roschenthaler Synthesis of functionalized bisphosphonates via click chemistry Org. Biomol. Chem. 5 2007 2361 2367
47. J. Broggi, S. Diez-Gonzalez, J.L. Petersen, S. Berteina-Raboin, S.P. Nolan, and L.A. Agrofoglio Study of copper(I) catalysts for the synthesis of carbanucleosides via azide-alkyne 1,3-dipolar cycloaddition Synthesis 2008 141 148
48. S.V. Poecke, A. Negri, F. Gago, I.V. Daele, N. Solaroli, A. Karlsson, J. Balzarini, and S.V. Calenbergh 3′-[4-Aryl-(1,2,3-triazol-1-yl)]-3′- deoxythymidine analogues as potent and selective inhibitors of human mitochondrial thymidine kinase J. Med. Chem. 53 2010 2902 2912
49. T.O. Olomola, R. Klein, K.A. Lobb, Y. Sayed, and P.T. Kaye Towards the synthesis of coumarin derivatives as potential dual-action HIV-1 protease and reverse transcriptase inhibitors Tetrahedron Lett. 51 2010 6325 6328
50. J. Lin, V. Roy, L. Wang, L. You, L.A. Agrofoglio, D. Deville-Bonne, T.R. McBrayer, S.J. Coats, R.F. Schinazi, and S. Eriksson 3′-(1,2,3-Triazol-1- yl)-3′-deoxythymidine analogs as substrates for human and ureaplasma parvum thymidine kinase for structure-activity investigations Bioorg. Med. Chem. 18 2010 3216
51. S.M. Park, J. Woo, E. Jeon, and B.H. Kim Synthesis of AZT-based cationic lipids and in vitro evaluation of siRNA delivery Chem. Commun. 46 2010 1523 1525
52. R. Kumar, A. El-Sagheer, J. Tumpane, P. Lincoln, L.M. Wilhelmsson, and T. Brown Template-directed oligonucleotide strand ligation, covalent intramolecular DNA circularization and catenation using click chemistry J. Am. Chem. Soc. 129 2007 6859 6864
53. R. Lucas, V. Neto, A.H. Bouazza, R. Zerrouki, R. Granet, P. Krausz, and Y. Champavier Microwave-assisted synthesis of a triazole-linked 3′-5′dithymidine using click chemistry Tetrahedron Lett. 49 2008 1004 1007
54. V.V. Rostovtsev, L.G. Green, V.V. Fokin, and K.B. Sharpless A stepwise Huisgen cycloaddition process: copper(I)-catalyzed regioselective ligation of azides and terminal alkynes Angew. Chem. Int. Ed. 41 2002 2596 2599
55. C.W. Tornøe, C. Christensen, and M. Meldal Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides J. Org. Chem. 67 2002 3057 3064
56. L. Rong, and P. Bates Analysis of the subgroup A avian sarcoma and leukosis virus receptor: the 40-residue, cysteine-rich, low-density lipoprotein receptor repeat motif of Tva is sufficient to mediate viral entry J. Virol. 69 1995 4847 4853
57. J. Carmichael, W.G. DeGraff, A.F. Gazdar, J.D. Minna, and J.B. Mitchell Evaluation of a tetrazolium-based semiautomated colorimetric assay: assessment of radiosensitivity Cancer Res. 47 1987 943 946
58. J. He, S. Choe, R. Walker, P. Di Marzio, D.O. Morgan, and N.R. Landau Human immunodeficiency virus type 1 viral protein R (Vpr) arrests cells in the G2 phase of the cell cycle by inhibiting p34cdc2 activity J. Virol. 69 1995 6705 6711
59. R.I. Connor, B.K. Chen, S. Choe, and N.R. Landau Vpr is required for efficient replication of human immunodeficiency virus type-1 in mononuclear phagocytes Virology 206 1995 935 944
60. L.-L. Gao, X.-Y. Wang, J.-S. Lin, Y.-H. Zhang, and Y. Li Efficacies of β-l-D4A against hepatitis B virus in 2.2.15 cells World J. Gastroenterol. 14 2008 1263 1267
61. B. Jahn, E. Martin, A. Stueben, and S. Bhakdi Susceptibility testing of Candida albicans and Aspergillus species by a simple microtiter menadione-augmented 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide assay J. Clin. Microbiol. 33 1995 661 667
62. T.G. Kim, S.Y. Kang, K.K. Jung, J.H. Kang, E. Lee, H.M. Han, and S.H. Kim Antiviral activities of extracts isolated from Terminalis chebula Retz., Sanguisorba officinalis L., Rubus coreanus Miq. and Rheum palmatum L. against hepatitis B virus Phytother. Res. 15 2001 718 720
63. X. Cui, Y. Inagaki, H. Xu, D. Wang, F. Qi, N. Kokudo, D. Fang, and W. Tang Anti-hepatitis B virus activities of cinobufacini and its active components bufalin and cinobufagin in HepG2.2.15 cells Biol. Pharm. Bull. 33 2010 1728 1732
64. R. Pang, J. Tao, S. Zhang, J. Zhu, X. Le, L. Zhao, P. Ye, and Y. Zhu In vitro anti-hepatitis B virus effect of Hypericum perforatum L J. Huazhong Univ. Sci. Technol. Med. Sci. 30 2010 98 102
65. J. Li, H. Huang, M. Feng, W. Zhou, X. Shi, and P. Zhou In vitro and in vivo anti-hepatitis B virus activities of a plant extract from Geranium carolinianum L Antiviral Res. 79 2008 114 120