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Volumn 19, Issue 10, 2013, Pages 1880-1897

From the chemistry of Epoxy-Sugar nucleosides to the discovery of Anti-HIV Agent 4'-ethynylstavudine-Festinavir

Author keywords

Anti HIV 1 agent; Epoxide; NRTIs; Nucleoside; Organoaluminum reagent; Stavudine; Sugar

Indexed keywords

ALUMINUM; ANTIVIRUS AGENT; FESTINAVIR; LAMIVUDINE; MITOCHONDRIAL DNA; NONNUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITOR; NUCLEOSIDE DERIVATIVE; SILICON; STAVUDINE; SUGAR; THYMIDINE KINASE; THYMIDINE PHOSPHORYLASE; UNCLASSIFIED DRUG;

EID: 84876712884     PISSN: 13816128     EISSN: 18734286     Source Type: Journal    
DOI: 10.2174/1381612811319100011     Document Type: Review
Times cited : (10)

References (63)
  • 2
    • 77649232123 scopus 로고    scopus 로고
    • Therapeutic strategies underpinning the development of novel techniques for the treatment of HIV infection
    • Tan JJ, Chong XJ, Hu LM, Wang CX, Jia L, Liang XL. Therapeutic strategies underpinning the development of novel techniques for the treatment of HIV infection. Drug Discov. Today 2010; 15(5/6): 186-97.
    • (2010) Drug Discov. Today , vol.15 , Issue.5-6 , pp. 186-197
    • Tan, J.J.1    Chong, X.J.2    Hu, L.M.3    Wang, C.X.4    Jia, L.5    Liang, X.L.6
  • 3
    • 0008004359 scopus 로고
    • Recent development of anti-HIV nucleosides
    • Matsuda A. Recent development of anti-HIV nucleosides. J Synth Org Chem Jpn 1990; 48(10): 907-20.
    • (1990) J Synth Org Chem Jpn , vol.48 , Issue.10 , pp. 907-920
    • Matsuda, A.1
  • 4
    • 0035038033 scopus 로고    scopus 로고
    • Sugar-modified nucleosides in past 10 years, a review
    • Ichikawa E, Kato K. Sugar-modified nucleosides in past 10 years, a review. Current Medicinal Chemistry 2001; 8(4): 385-423.
    • (2001) Current Medicinal Chemistry , vol.8 , Issue.4 , pp. 385-423
    • Ichikawa, E.1    Kato, K.2
  • 5
    • 0000335222 scopus 로고
    • AIDS-driven nucleoside chemistry
    • Huryn DM, Okabe M. AIDS-driven nucleoside chemistry. Chem Rev 1992; 92(8): 1745-68.
    • (1992) Chem Rev , vol.92 , Issue.8 , pp. 1745-1768
    • Huryn, D.M.1    Okabe, M.2
  • 6
    • 36749073433 scopus 로고    scopus 로고
    • The design of drugs for HIV and HCV
    • De Clercq E. The design of drugs for HIV and HCV. Nature Review 2007; 6: 1001-18.
    • (2007) Nature Review , vol.6 , pp. 1001-1018
    • de Clercq, E.1
  • 7
    • 0014433114 scopus 로고
    • Purine nucleosdes. XXII. synthesis of angustmycin A (decoynine) and related unsaturated nucleosides
    • McCarthy JR Jr, Robins RK, Robins MJ. Purine nucleosdes. XXII. synthesis of angustmycin A (decoynine) and related unsaturated nucleosides. J Am Chem Soc 1968; 90(17): 4993-9.
    • (1968) J Am Chem Soc , vol.90 , Issue.17 , pp. 4993-4999
    • McCarthy Jr., J.R.1    Robins, R.K.2    Robins, M.J.3
  • 8
    • 0029731762 scopus 로고    scopus 로고
    • Nucleosides and Nucleotides. 158. 1-(3-C-Ethynyl----D-ribo-pentofuranosyl) cytosine, 1-(3-C-ethynyl----D-ribo-pentofuranosyl)uracil and their nucleobase analogues as new potential multifunctional antitumor nucleosides with a broad spectrum of activity
    • Hattori H, Tanaka M, Fukushima M, Sasaki T, Matsuda A. Nucleosides and Nucleotides. 158. 1-(3-C-Ethynyl----D-ribo-pentofuranosyl) cytosine, 1-(3-C-ethynyl----D-ribo-pentofuranosyl)uracil and their nucleobase analogues as new potential multifunctional antitumor nucleosides with a broad spectrum of activity. J Med Chem 1996; 39(25): 5005-11.
    • (1996) J Med Chem , vol.39 , Issue.25 , pp. 5005-5011
    • Hattori, H.1    Tanaka, M.2    Fukushima, M.3    Sasaki, T.4    Matsuda, A.5
  • 9
    • 0026501018 scopus 로고
    • Synthesis of 4β-cyanothymidine and analogs as potent inhibitors of HIV
    • O-Yang C, Wu HY, Fraser-Smith EB, Walker KAM. Synthesis of 4β-cyanothymidine and analogs as potent inhibitors of HIV. Tetrahedron Lett 1992; 33(1): 37-40.
    • (1992) Tetrahedron Lett , vol.33 , Issue.1 , pp. 37-40
    • O-Yang, C.1    Wu, H.Y.2    Fraser-Smith, E.B.3    Walker, K.A.M.4
  • 10
    • 0028862807 scopus 로고
    • Divergent and stereocontrolled approach to the synthesis of uracil nucleosides branched at the anomeric position
    • Itoh Y, Haraguchi K, Tanaka H, Gen E, Miyasaka T. Divergent and stereocontrolled approach to the synthesis of uracil nucleosides branched at the anomeric position. J Org Chem 1995; 60(3): 656-62.
    • (1995) J Org Chem , vol.60 , Issue.3 , pp. 656-662
    • Itoh, Y.1    Haraguchi, K.2    Tanaka, H.3    Gen, E.4    Miyasaka, T.5
  • 11
    • 0036828138 scopus 로고    scopus 로고
    • A highly stereoselective samarium diiodide-promoted aldol reaction with 1β-phenylseleno-2β-keto nucleosides. synthesis of 1β----branched uridine derivative
    • Kodama T, Shuto S, Ichikawa S, Matsuda A. A highly stereoselective samarium diiodide-promoted aldol reaction with 1β-phenylseleno-2β-keto nucleosides. synthesis of 1β----branched uridine derivative. J Org Chem 2002; 67(22): 7706-15.
    • (2002) J Org Chem , vol.67 , Issue.22 , pp. 7706-7715
    • Kodama, T.1    Shuto, S.2    Ichikawa, S.3    Matsuda, A.4
  • 12
    • 0037424423 scopus 로고    scopus 로고
    • Stereoselective synthesis of 1β-C-branched arabinofuranosyl nucleosides via anomeric radicals generated by 1,2-acyloxy migration
    • Haraguchi K, Itoh Y, Matsumoto K, Nakamura KT, Tanaka H. Stereoselective synthesis of 1β-C-branched arabinofuranosyl nucleosides via anomeric radicals generated by 1,2-acyloxy migration. J Org Chem. 2003; 68(5): 2006-9.
    • (2003) J Org Chem. , vol.68 , Issue.5 , pp. 2006-2009
    • Haraguchi, K.1    Itoh, Y.2    Matsumoto, K.3    Nakamura, K.T.4    Tanaka, H.5
  • 13
    • 0037162663 scopus 로고    scopus 로고
    • Nucleophilic addition of benzenethiol to 1β,2β-unsaturated nucleosides: 1β-Cphenylthio-2β-deoxynucleosides as anomeric radical precursors
    • Kumamoto H, Murasaki M, Haraguchi K, Tanaka H. Nucleophilic addition of benzenethiol to 1β,2β-unsaturated nucleosides: 1β-Cphenylthio-2β-deoxynucleosides as anomeric radical precursors. J Org Chem. 2002; 67(17): 6124-30.
    • (2002) J Org Chem. , vol.67 , Issue.17 , pp. 6124-6130
    • Kumamoto, H.1    Murasaki, M.2    Haraguchi, K.3    Tanaka, H.4
  • 14
    • 0035354786 scopus 로고    scopus 로고
    • An efficient method for the preparation of 1β-branched-chain sugar pyrimidine ribonucleosides from uridine: The first conversion of a natural nucleoside into 1β-substituted ribonucleosides
    • Kodama T, Shuto S, Nomura M, Matsuda, A. An efficient method for the preparation of 1β-branched-chain sugar pyrimidine ribonucleosides from uridine: the first conversion of a natural nucleoside into 1β-substituted ribonucleosides. Chem Eur J 2001; 7(12): 2332-40.
    • (2001) Chem Eur J , vol.7 , Issue.12 , pp. 2332-2340
    • Kodama, T.1    Shuto, S.2    Nomura, M.3    Matsuda, A.4
  • 15
    • 0033535074 scopus 로고    scopus 로고
    • Nucleosides and nucleotides. 183. synthesis of 4β-branched thymidines as a new type of antiviral agent
    • Sugimoto I, Shuto S, Mori S, Shigeta S, Matsuda A. Nucleosides and nucleotides. 183. synthesis of 4β-branched thymidines as a new type of antiviral agent. Bioorg Med Chem Lett.1999; 9(3): 385-8.
    • (1999) Bioorg Med Chem Lett. , vol.9 , Issue.3 , pp. 385-388
    • Sugimoto, I.1    Shuto, S.2    Mori, S.3    Shigeta, S.4    Matsuda, A.5
  • 16
    • 85037455306 scopus 로고
    • Synthetically useful reactions of epoxides
    • For a review, see
    • For a review, see: Smith JG. Synthetically useful reactions of epoxides. Synthesis 1984; 629-56.
    • (1984) Synthesis , pp. 629-656
    • Smith, J.G.1
  • 17
    • 0023122760 scopus 로고
    • The synthesis of some branched-chain-sugar nucleoside analogues
    • Ashwell M, Jones AS, Walker RT. The synthesis of some branched-chain-sugar nucleoside analogues. Nucleic Acids Res 1987; 15(5): 2157-66.
    • (1987) Nucleic Acids Res , vol.15 , Issue.5 , pp. 2157-2166
    • Ashwell, M.1    Jones, A.S.2    Walker, R.T.3
  • 18
    • 84985666791 scopus 로고
    • A convenient preparation of acetone solution of dimethyldioxirane
    • Adam W, Balas J, Hadjarapoglou L. A convenient preparation of acetone solution of dimethyldioxirane., Chem Ber 1991; 124(10): 2377.
    • (1991) Chem Ber , vol.124 , Issue.10 , pp. 2377
    • Adam, W.1    Balas, J.2    Hadjarapoglou, L.3
  • 19
    • 24044469796 scopus 로고
    • Epoxidation of alkenes by dioxirane intermediates generated in the reaction of potassium caroate with ketones
    • Curci R, Fiorentiono M, Troisi L, Edwards JO, Pater RH. Epoxidation of alkenes by dioxirane intermediates generated in the reaction of potassium caroate with ketones. J Org Chem 1980; 45(23): 4758-60.
    • (1980) J Org Chem , vol.45 , Issue.23 , pp. 4758-4760
    • Curci, R.1    Fiorentiono, M.2    Troisi, L.3    Edwards, J.O.4    Pater, R.H.5
  • 20
    • 30144437908 scopus 로고
    • Dioxiranes: Synthesis and reaction of methyldioxiranes
    • Murray RW, Jeyaman R. Dioxiranes: synthesis and reaction of methyldioxiranes. J Org Chem 1985; 50(16): 2847-53.
    • (1985) J Org Chem , vol.50 , Issue.16 , pp. 2847-2853
    • Murray, R.W.1    Jeyaman, R.2
  • 21
    • 1642299991 scopus 로고    scopus 로고
    • Ring opening of nucleoside 1',2'-epoxides with organoaluminum reagents: Stereoselective entry to ribonucleosides branched at the anomeric position
    • Haraguchi K, Kubota Y, Tanaka H. Ring opening of nucleoside 1',2'-epoxides with organoaluminum reagents: stereoselective entry to ribonucleosides branched at the anomeric position. J Org Chem 2004; 69(6): 1831-6.
    • (2004) J Org Chem , vol.69 , Issue.6 , pp. 1831-1836
    • Haraguchi, K.1    Kubota, Y.2    Tanaka, H.3
  • 22
    • 77953122964 scopus 로고    scopus 로고
    • Electrophilic glycosidation employing 3,5-O-(di-tertbutylsilylene)-erythro-furanoid glycal leads to exclusive formation of the α-anomer: Synthesis of 2β-deoxynucleosides and its 1β-branched analogues
    • Haraguchi K, Konno K, Yamada K, Kitagawa Y, Nakamura KT, Tanaka H. Electrophilic glycosidation employing 3,5-O-(di-tertbutylsilylene)-erythro-furanoid glycal leads to exclusive formation of the α-anomer: synthesis of 2β-deoxynucleosides and its 1β-branched analogues. Tetrahedron 2010; 66(25): 4587-600.
    • (2010) Tetrahedron , vol.66 , Issue.25 , pp. 4587-4600
    • Haraguchi, K.1    Konno, K.2    Yamada, K.3    Kitagawa, Y.4    Nakamura, K.T.5    Tanaka, H.6
  • 23
    • 32144464364 scopus 로고    scopus 로고
    • Anti versus syn opening of epoxides derived from 9-(3-deoxy-dd-D-glycero-pento-3-enofuranosyl)adenine with Me3Al: Factors controlling the stereoselectivity
    • Kubota Y, Haraguchi K, Kunikata M, Hayashi M, Ohkawa M, Tanaka H. Anti versus syn opening of epoxides derived from 9-(3-deoxy-dd-D-glycero-pento-3-enofuranosyl)adenine with Me3Al: factors controlling the stereoselectivity. J Org Chem 2006; 71(3): 1099-103.
    • (2006) J Org Chem , vol.71 , Issue.3 , pp. 1099-1103
    • Kubota, Y.1    Haraguchi, K.2    Kunikata, M.3    Hayashi, M.4    Ohkawa, M.5    Tanaka, H.6
  • 25
    • 0026501018 scopus 로고
    • Synthesis of 4β-cyanothymidine and analogs as potent inhibitors of HIV
    • O-Yang C, Wu HY, Fraser-Smith EB, Walker KAM. Synthesis of 4β-cyanothymidine and analogs as potent inhibitors of HIV. Tetrahedron Lett 1992; 33(1): 37-40.
    • (1992) Tetrahedron Lett , vol.33 , Issue.1 , pp. 37-40
    • O-Yang, C.1    Wu, H.Y.2    Fraser-Smith, E.B.3    Walker, K.A.M.4
  • 26
    • 0033535074 scopus 로고    scopus 로고
    • Synthesis of 4β----branched thymidines as a new type of antiviral agent
    • Sugimoto I, Shuto S, Mori S, Shigeta S, Matsuda A. Synthesis of 4β----branched thymidines as a new type of antiviral agent. Bioorg Med Chem Lett 1999; 9(3): 385-8.
    • (1999) Bioorg Med Chem Lett , vol.9 , Issue.3 , pp. 385-388
    • Sugimoto, I.1    Shuto, S.2    Mori, S.3    Shigeta, S.4    Matsuda, A.5
  • 27
    • 0033614990 scopus 로고    scopus 로고
    • Synthesis and biological activities of 4β----branched-chain sugar pyrimidine nucleosides
    • Nomura M, Shuto S, Tanaka M, et al. Synthesis and biological activities of 4β----branched-chain sugar pyrimidine nucleosides J Med Chem 1999; 42(15): 2901-8.
    • (1999) J Med Chem , vol.42 , Issue.15 , pp. 2901-2908
    • Nomura, M.1    Shuto, S.2    Tanaka, M.3
  • 28
    • 0034676266 scopus 로고    scopus 로고
    • Synthesis of 4β-C-ethynyl-Darabino-and 4β-C-ethynyl-2β-deoxy----D-ribo-pentofuranosylpyrimidines and-purines and evaluation of their anti-HIV activity
    • Ohrui H, Kohgo S, Kitano K, et al. Synthesis of 4β-C-ethynyl-Darabino-and 4β-C-ethynyl-2β-deoxy----D-ribo-pentofuranosylpyrimidines and-purines and evaluation of their anti-HIV activity. J Med Chem 2000; 43(23); 4516-25.
    • (2000) J Med Chem , vol.43 , Issue.23 , pp. 4516-4525
    • Ohrui, H.1    Kohgo, S.2    Kitano, K.3
  • 29
    • 0034744423 scopus 로고    scopus 로고
    • 4β-Ethynyl nucleoside analogs: Potent inhibitors of multidrug-resistant human immunodeficiency virus varinats in vitro
    • Kodama E, Kohgo S, Kitano K, et al. 4β-Ethynyl nucleoside analogs: potent inhibitors of multidrug-resistant human immunodeficiency virus varinats in vitro. Antimicrob Agents Chemother 2001; 45(5): 1539-46.
    • (2001) Antimicrob Agents Chemother , vol.45 , Issue.5 , pp. 1539-1546
    • Kodama, E.1    Kohgo, S.2    Kitano, K.3
  • 30
    • 0033614990 scopus 로고    scopus 로고
    • Synthesis and biological activity of 4β-alpha-C-branched-chain-sugar pyrimidine nucleosides
    • Nomura S, Shuto S, Tanaka M, et al. Synthesis and biological activity of 4β-alpha-C-branched-chain-sugar pyrimidine nucleosides J Med Chem 1999; 42(15); 2901-8.
    • (1999) J Med Chem , vol.42 , Issue.15 , pp. 2901-2908
    • Nomura, S.1    Shuto, S.2    Tanaka, M.3
  • 31
    • 0034676266 scopus 로고    scopus 로고
    • Synthesis of 4β-C-ethynyl beta-D-arabino and 4β-C-ethynyl-beta-D-ribo-pentofuranosylpyrimidine and-purines and evaluation of their anti-HIV activity
    • Ohrui H, Kohgo S, Kitano K, et al. Synthesis of 4β-C-ethynyl beta-D-arabino and 4β-C-ethynyl-beta-D-ribo-pentofuranosylpyrimidine and-purines and evaluation of their anti-HIV activity. J Med Chem 2000; 43(23): 4516-25.
    • (2000) J Med Chem , vol.43 , Issue.23 , pp. 4516-4525
    • Ohrui, H.1    Kohgo, S.2    Kitano, K.3
  • 32
    • 0041765008 scopus 로고    scopus 로고
    • Ring opening of 4β,5β-epoxynucleosides: A novel stereoselective entry to 4β-C-branched nucleosides
    • Haraguchi K, Takeda S, Tanaka H. Ring opening of 4β,5β-epoxynucleosides: a novel stereoselective entry to 4β-C-branched nucleosides. Org Lett 2003; 5(9): 1399-402.
    • (2003) Org Lett , vol.5 , Issue.9 , pp. 1399-1402
    • Haraguchi, K.1    Takeda, S.2    Tanaka, H.3
  • 33
    • 0141545085 scopus 로고    scopus 로고
    • Synthesis of a highly active new anti-HIV agent 2β,3β-didehydro-3β-deoxy-4β-ethynylthymidine
    • Haraguchi K, Takeda S, Tanaka H, et al. Synthesis of a highly active new anti-HIV agent 2β,3β-didehydro-3β-deoxy-4β-ethynylthymidine. Bioorg Med Chem Lett 2003; 13(19): 3775-7.
    • (2003) Bioorg Med Chem Lett , vol.13 , Issue.19 , pp. 3775-3777
    • Haraguchi, K.1    Takeda, S.2    Tanaka, H.3
  • 34
    • 2142713068 scopus 로고    scopus 로고
    • Novel 4β-substituted stavudine analog with improved anti-human immunodeficiency virus activity and decreased cytotoxicity
    • Dutschman GE, Grill SP, Gullen EA, et al. Novel 4β-substituted stavudine analog with improved anti-human immunodeficiency virus activity and decreased cytotoxicity. Antimicrob Agents Chemother 2004; 48(5): 1640-6.
    • (2004) Antimicrob Agents Chemother , vol.48 , Issue.5 , pp. 1640-1646
    • Dutschman, G.E.1    Grill, S.P.2    Gullen, E.A.3
  • 35
    • 23044505480 scopus 로고    scopus 로고
    • Anti-human immunodeficiency virus type 1 activity and resistance profile of 2β,3β-didehydro-3β-deoxy-4β-ethynylthymidine in vitro
    • Nitanda T, Wang X, Kumamoto H, et al. Anti-human immunodeficiency virus type 1 activity and resistance profile of 2β,3β-didehydro-3β-deoxy-4β-ethynylthymidine in vitro. Antimicrob Agents Chemother 2005; 49(8): 3355-60.
    • (2005) Antimicrob Agents Chemother , vol.49 , Issue.8 , pp. 3355-3360
    • Nitanda, T.1    Wang, X.2    Kumamoto, H.3
  • 36
    • 2542534499 scopus 로고    scopus 로고
    • Synthesis and anti-HIV activity of 4β-cyano-2β,3β-didehydro-3β-deoxythymidine
    • Haraguchi K, Itoh Y, Takeda S, et al. Synthesis and anti-HIV activity of 4β-cyano-2β,3β-didehydro-3β-deoxythymidine. Nucleosdes Nucletides Nucleic Acids 2004; 23(4): 647-4.
    • (2004) Nucleosdes Nucletides Nucleic Acids , vol.23 , Issue.4 , pp. 647-654
    • Haraguchi, K.1    Itoh, Y.2    Takeda, S.3
  • 37
    • 23744503171 scopus 로고    scopus 로고
    • 4β-ethynylstavudine (4β-Ed4T) has potent anti-HIV activity with reduced toxicity and shows a unique activity profile against drug resistant mutants
    • Tanaka H, Haraguchi K, Kumamoto H, Baba M, Cheng YC. 4β-ethynylstavudine (4β-Ed4T) has potent anti-HIV activity with reduced toxicity and shows a unique activity profile against drug resistant mutants. Antiviral Chemistry & Chemotherapy 2005; 16(4): 217-21.
    • (2005) Antiviral Chemistry & Chemotherapy , vol.16 , Issue.4 , pp. 217-221
    • Tanaka, H.1    Haraguchi, K.2    Kumamoto, H.3    Baba, M.4    Cheng, Y.C.5
  • 38
    • 15944419796 scopus 로고    scopus 로고
    • Synthesis of (±)-4β-ehtynyl-and 4β-cyano carbocyclic analogues of stavudine (d4T)
    • Kumamoto H, Haraguchi K, Tanaka H, et al. Synthesis of (±)-4β-ehtynyl-and 4β-cyano carbocyclic analogues of stavudine (d4T). Nucleosides Nucleotides Nucleic Acids 2005; 24(2): 73-83.
    • (2005) Nucleosides Nucleotides Nucleic Acids , vol.24 , Issue.2 , pp. 73-83
    • Kumamoto, H.1    Haraguchi, K.2    Tanaka, H.3
  • 39
    • 67949086866 scopus 로고    scopus 로고
    • Synthesis of (±)-4β-ehtynyl-5β,5β-difluoro-2β,3β-dehydro-3β-deoxy-carbocyclic thymidine: A difluoromethylidene analogue of promising anti-HIV agent Ed4T
    • Kumamoto H, Haraguchi K, Ida M, et al. Synthesis of (±)-4β-ehtynyl-5β,5β-difluoro-2β,3β-dehydro-3β-deoxy-carbocyclic thymidine: a difluoromethylidene analogue of promising anti-HIV agent Ed4T. Tetrahedron 2009; 65(36): 7630-6.
    • (2009) Tetrahedron , vol.65 , Issue.36 , pp. 7630-7636
    • Kumamoto, H.1    Haraguchi, K.2    Ida, M.3
  • 40
    • 33845951417 scopus 로고    scopus 로고
    • Synthesis and anti-HIV-1 activity of 4β-branched (-)-4β-thiostavudines
    • Kumamoto H, Nakai T, Haraguchi K, et al. Synthesis and anti-HIV-1 activity of 4β-branched (-)-4β-thiostavudines. J Med Chem. 2006; 49(26): 7861-67.
    • (2006) J Med Chem. , vol.49 , Issue.26 , pp. 7861-7867
    • Kumamoto, H.1    Nakai, T.2    Haraguchi, K.3
  • 41
    • 0024310253 scopus 로고
    • Multiple mutations in HIV-1 reverse transcriptase confer high-level resistance to zidovudine (AZT)
    • Larder BA, Kemp SD, Multiple mutations in HIV-1 reverse transcriptase confer high-level resistance to zidovudine (AZT). Science, 1989; 246(4934): 1155-8.
    • (1989) Science , vol.246 , Issue.4934 , pp. 1155-1158
    • Larder, B.A.1    Kemp, S.D.2
  • 42
    • 0027409698 scopus 로고
    • Characterization of human immunodeficiency viruses resistant to oxathiolane-cytosine nucleosides
    • Schinazi RF, Lloyd RM Jr, Nguyen MH, et al. Characterization of human immunodeficiency viruses resistant to oxathiolane-cytosine nucleosides. Antimicrob Agents Chemother 1993; 37(4): 875-81.
    • (1993) Antimicrob Agents Chemother , vol.37 , Issue.4 , pp. 875-881
    • Schinazi, R.F.1    Lloyd Jr., R.M.2    Nguyen, M.H.3
  • 43
    • 0038372726 scopus 로고    scopus 로고
    • Extended treatment with tenofovir disoproxil fumarate in treatmentexperienced HIV-1-infected patients: Genotypic, phenotypic, and rebound analyses
    • Margot NA, Isaacson E, McGowan I, Cheng A, Miller MD. Extended treatment with tenofovir disoproxil fumarate in treatmentexperienced HIV-1-infected patients: genotypic, phenotypic, and rebound analyses. J Acquir Immune Defic Syndr. 2003; 33(1): 15-21.
    • (2003) J Acquir Immune Defic Syndr. , vol.33 , Issue.1 , pp. 15-21
    • Margot, N.A.1    Isaacson, E.2    McGowan, I.3    Cheng, A.4    Miller, M.D.5
  • 44
    • 2342661255 scopus 로고    scopus 로고
    • K65R, TAMs and tenofovir
    • Miller MD. K65R, TAMs and tenofovir. AIDS Rev. 2004; 6(1): 22-33.
    • (2004) AIDS Rev. , vol.6 , Issue.1 , pp. 22-33
    • Miller, M.D.1
  • 45
    • 0036839746 scopus 로고    scopus 로고
    • RT processivities in vitro, consistent with a potential fitness defect in vivo and the low prevalence of the K65R mutation among isolates from antiretroviral agent-experienced patients
    • White KL, Margot NA, Wrin T, Petropoulos CJ, Miller MD, Naeger LK. RT processivities in vitro, consistent with a potential fitness defect in vivo and the low prevalence of the K65R mutation among isolates from antiretroviral agent-experienced patients. Antimicrob Agents Chemother. 2002; 46(10): 3437-46.
    • (2002) Antimicrob Agents Chemother. , vol.46 , Issue.10 , pp. 3437-3446
    • White, K.L.1    Margot, N.A.2    Wrin, T.3    Petropoulos, C.J.4    Miller, M.D.5    Naeger, L.K.6
  • 46
    • 0028940084 scopus 로고
    • Emergence of human immunodeficiency virus type 1 variants with resistance to multiple dideoxynucleosides in patients receiving therapy with dideoxynucleosides
    • Shirasaka T, Kavlick MF, Ueno T, et al. Emergence of human immunodeficiency virus type 1 variants with resistance to multiple dideoxynucleosides in patients receiving therapy with dideoxynucleosides. Proc Natl Acad Sci U S A 1995; 92(6): 2398-402.
    • (1995) Proc Natl Acad Sci U S A , vol.92 , Issue.6 , pp. 2398-2402
    • Shirasaka, T.1    Kavlick, M.F.2    Ueno, T.3
  • 47
    • 34250811908 scopus 로고    scopus 로고
    • Mutations in human immunodeficiency virus type 1 RNase H primer grip enhance 3β-azido-3β-deoxythymidine resistance
    • Delviks-Frankenberry, KA, Nikolenko GN, Barr R, Pathak VK. Mutations in human immunodeficiency virus type 1 RNase H primer grip enhance 3β-azido-3β-deoxythymidine resistance. J Virol. 2007; 81(13): 6837-45.
    • (2007) J Virol. , vol.81 , Issue.13 , pp. 6837-6845
    • Delviks-Frankenberry, K.A.1    Nikolenko, G.N.2    Barr, R.3    Pathak, V.K.4
  • 48
    • 33846063300 scopus 로고    scopus 로고
    • Mutations in the connection domain of HIV-1 reverse transcriptase increase 3β-azido-3β-deoxythymidine resistance
    • Nikolenko GN, Delviks-Frankenberry KA, Palmer S, et al. Mutations in the connection domain of HIV-1 reverse transcriptase increase 3β-azido-3β-deoxythymidine resistance. Proc Natl Acad Sci U S A. 2007; 104(1): 317-22.
    • (2007) Proc Natl Acad Sci U S A. , vol.104 , Issue.1 , pp. 317-322
    • Nikolenko, G.N.1    Delviks-Frankenberry, K.A.2    Palmer, S.3
  • 49
    • 41149145592 scopus 로고    scopus 로고
    • Amino acid mutation N348I in the connection subdomain of human immunodeficiency virus type 1 reverse transcriptase confers multiclass resistance to nucleoside and nonnucleoside reverse transcriptase inhibitors
    • Hachiya A, Kodama EN, Sarafianos SG, et al. Amino acid mutation N348I in the connection subdomain of human immunodeficiency virus type 1 reverse transcriptase confers multiclass resistance to nucleoside and nonnucleoside reverse transcriptase inhibitors. J Virol. 2008; 82(7); 3261-70.
    • (2008) J Virol. , vol.82 , Issue.7 , pp. 3261-3270
    • Hachiya, A.1    Kodama, E.N.2    Sarafianos, S.G.3
  • 50
    • 38049028352 scopus 로고    scopus 로고
    • N348I in the Connection Domain of HIV-1 Reverse Transcriptase Confers Zidovudine and Nevirapine Resistance
    • Yap SH, Sheen, CW, et al. N348I in the Connection Domain of HIV-1 Reverse Transcriptase Confers Zidovudine and Nevirapine Resistance. PLoS Med 2007; 4: e335.
    • (2007) PLoS Med , vol.4
    • Yap, S.H.1    Sheen, C.W.2
  • 51
    • 52049107430 scopus 로고    scopus 로고
    • Connection domain mutations N348I and A360V in HIV-1 reverse transcriptase enhance resistance to 3'-azido-3'-deoxythymidine through both RNase H-dependent and-independent mechanisms
    • Ehteshami M, Beilhartz GL, Scarth BJ, et al. Connection domain mutations N348I and A360V in HIV-1 reverse transcriptase enhance resistance to 3'-azido-3'-deoxythymidine through both RNase H-dependent and-independent mechanisms J Biol Chem 2008; 283(32): 22222-32.
    • (2008) J Biol Chem , vol.283 , Issue.32 , pp. 22222-22232
    • Ehteshami, M.1    Beilhartz, G.L.2    Scarth, B.J.3
  • 52
    • 0032555281 scopus 로고    scopus 로고
    • Characterization of the native and recombinant catalytic subunit of human DNA polymerase gamma: Identification of residues critical for exonuclease activity and dideoxynucleotide sensitivity
    • Longley MJ, Ropp PA, Lim SE, Copeland WC. Characterization of the native and recombinant catalytic subunit of human DNA polymerase gamma: identification of residues critical for exonuclease activity and dideoxynucleotide sensitivity. Biochemistry 1998; 37(29): 10529-39.
    • (1998) Biochemistry , vol.37 , Issue.29 , pp. 10529-10539
    • Longley, M.J.1    Ropp, P.A.2    Lim, S.E.3    Copeland, W.C.4
  • 53
    • 0024381627 scopus 로고
    • Delayed cytotoxicity and selective loss of mitochondrial DNA in cells treated with the anti-human immunodeficiency virus compound 2β,3β-dideoxycytidine
    • Chen CH, Cheng YC. Delayed cytotoxicity and selective loss of mitochondrial DNA in cells treated with the anti-human immunodeficiency virus compound 2β,3β-dideoxycytidine. J Biol Chem 1989; 264(20): 11934-7.
    • (1989) J Biol Chem , vol.264 , Issue.20 , pp. 11934-11937
    • Chen, C.H.1    Cheng, Y.C.2
  • 54
    • 0025729392 scopus 로고
    • Effect of anti-human immunodeficiency virus nucleoside analogs on mitochondrial DNA and its implication for delayed toxicity
    • Chen CH, Vazquez-Padua M, Cheng YC. Effect of anti-human immunodeficiency virus nucleoside analogs on mitochondrial DNA and its implication for delayed toxicity. Mol Pharmacol. 1991; 39(5): 625-8.
    • (1991) Mol Pharmacol. , vol.39 , Issue.5 , pp. 625-628
    • Chen, C.H.1    Vazquez-Padua, M.2    Cheng, Y.C.3
  • 55
    • 33847027993 scopus 로고    scopus 로고
    • Highly selective action of triphosphate metabolite of 4β-ethynyl D4T: A novel anti-HIV compound against HIV-1 RT
    • Yang G, Dutschman GE, Wang CJ, et al. Highly selective action of triphosphate metabolite of 4β-ethynyl D4T: a novel anti-HIV compound against HIV-1 RT. Antiviral Res 2007; 73(3): 185-91.
    • (2007) Antiviral Res , vol.73 , Issue.3 , pp. 185-191
    • Yang, G.1    Dutschman, G.E.2    Wang, C.J.3
  • 56
    • 44449119875 scopus 로고    scopus 로고
    • Mechanism of inhibition of human immunodeficiency virus type 1 reverse transcriptase by a stavudine analogue, 4β-ethynyl stavudine triphosphate
    • Yang G, Wang J, Cheng Y, et al. Mechanism of inhibition of human immunodeficiency virus type 1 reverse transcriptase by a stavudine analogue, 4β-ethynyl stavudine triphosphate. Antimicrob Agents Chemother 2008; 52(6): 2035-42.
    • (2008) Antimicrob Agents Chemother , vol.52 , Issue.6 , pp. 2035-2042
    • Yang, G.1    Wang, J.2    Cheng, Y.3
  • 57
    • 70350321279 scopus 로고    scopus 로고
    • Impact of Novel HIV-1 Reverse Transcriptase Mutations, P119S and T165A on 4β-ethynylthymidine Analog Resistance Profile
    • Yang G, Paintsil E, Dutschman GE, et al. Impact of Novel HIV-1 Reverse Transcriptase Mutations, P119S and T165A on 4β-ethynylthymidine Analog Resistance Profile. Antimicrob Agents and Chemother 2009; 53(11); 4640-6.
    • (2009) Antimicrob Agents and Chemother , vol.53 , Issue.11 , pp. 4640-4646
    • Yang, G.1    Paintsil, E.2    Dutschman, G.E.3
  • 58
    • 35848929439 scopus 로고    scopus 로고
    • Intracellular metabolism and persistence of the anti-human immunodeficiency virus activity of 2β,3β-didehydro-3β-deoxy-4β-ethynylthymidine, a novel thymidine analog
    • Paintsil E, Dutschman GE, Hu R, et al. Intracellular metabolism and persistence of the anti-human immunodeficiency virus activity of 2β,3β-didehydro-3β-deoxy-4β-ethynylthymidine, a novel thymidine analog. Antimicrob Agents Chemother 2007; 51(11): 3870-9.
    • (2007) Antimicrob Agents Chemother , vol.51 , Issue.11 , pp. 3870-3879
    • Paintsil, E.1    Dutschman, G.E.2    Hu, R.3
  • 59
    • 34248344120 scopus 로고    scopus 로고
    • Comparison of the phosphorylation of 4'-ethynyl 2β,3β-dihydro-3β-deoxythymidine with that of other anti-human immunodeficiency virus thymidine analogs
    • Hsu CH, Hu R, Dutschman GE, et al. Comparison of the phosphorylation of 4'-ethynyl 2β,3β-dihydro-3β-deoxythymidine with that of other anti-human immunodeficiency virus thymidine analogs. Antimicrob Agents Chemother 2007; 51(5): 1687-93.
    • (2007) Antimicrob Agents Chemother , vol.51 , Issue.5 , pp. 1687-1693
    • Hsu, C.H.1    Hu, R.2    Dutschman, G.E.3
  • 60
    • 67749095978 scopus 로고    scopus 로고
    • Study of the retention of metabolites of 4β-Ed4T, a novel anti-HIV-1 thymidine analog, in cells
    • Wang X, Tanaka H, Baba M, Cheng YC. Study of the retention of metabolites of 4β-Ed4T, a novel anti-HIV-1 thymidine analog, in cells. Antimicrob Agents Chemother 2009; 53(8): 3317-24.
    • (2009) Antimicrob Agents Chemother , vol.53 , Issue.8 , pp. 3317-3324
    • Wang, X.1    Tanaka, H.2    Baba, M.3    Cheng, Y.C.4
  • 61
    • 66349096006 scopus 로고    scopus 로고
    • Comparative study of the persistence of anti-HIV activity of deoxynucleoside HIV reverse transcriptase inhibitors after removal from culture
    • Paintsil E, Grill SP, Dutschman GE, Cheng YC. Comparative study of the persistence of anti-HIV activity of deoxynucleoside HIV reverse transcriptase inhibitors after removal from culture. AIDS Res Ther 2009; 6: 5.
    • (2009) AIDS Res Ther , vol.6 , pp. 5
    • Paintsil, E.1    Grill, S.P.2    Dutschman, G.E.3    Cheng, Y.C.4
  • 62
    • 0023258934 scopus 로고
    • 3β-azido-3β-deoxythymidine. An unusual nucleoside analogue that permeates the membrane of human erythrocytes and lymphocytes by nonfacilitated diffusion
    • Zimmerman TP, Mahony WB, Prus KL. 3β-azido-3β-deoxythymidine. An unusual nucleoside analogue that permeates the membrane of human erythrocytes and lymphocytes by nonfacilitated diffusion. J Biol Chem 1987; 262(12): 5748-54.
    • (1987) J Biol Chem , vol.262 , Issue.12 , pp. 5748-5754
    • Zimmerman, T.P.1    Mahony, W.B.2    Prus, K.L.3


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