메뉴 건너뛰기




Volumn 50, Issue 8, 2007, Pages 1828-1839

D- and L-2′,3′-didehydro-2′,3′-dideoxy-3′- fluoro-carbocyclic nucleosides: Synthesis, anti-HIV activity and mechanism of resistance

Author keywords

[No Author keywords available]

Indexed keywords

9 (2,3 DIDEOXY 2,3 DIDEHYDRO 3 FLUORO 6 HYDROXYMETHYLCYCLOPENT 2 ENYL)GUANINE; CARBOVIR; FLUORINE DERIVATIVE; GUANINE DERIVATIVE; GUANOSINE DERIVATIVE; LAMIVUDINE; NUCLEOSIDE DERIVATIVE; RNA DIRECTED DNA POLYMERASE; RNA DIRECTED DNA POLYMERASE INHIBITOR; UNCLASSIFIED DRUG;

EID: 34247212837     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm061304k     Document Type: Article
Times cited : (21)

References (34)
  • 1
    • 14944344464 scopus 로고    scopus 로고
    • New approaches toward anti-HIV chemotherapy
    • De Clercq, E. New approaches toward anti-HIV chemotherapy. J. Med. Chem. 2005, 48 (5), 1297-1313.
    • (2005) J. Med. Chem , vol.48 , Issue.5 , pp. 1297-1313
    • De Clercq, E.1
  • 2
    • 0023266214 scopus 로고    scopus 로고
    • Richman, D. D.; Fischl, M. A.; Grieco, M. H.; Gottlieb, M. S. Volherding, P. A.; Laskin, O. L.; Leedom, J. M.; Groopman, J. E. Mildvan, D.; Hirsch, M. S.; Jackson, G. G.; Durack, D. T.; Phil, D. Lusinoff-Lehrman, S. The AZT collaborative working group. The toxicity of azidothymidine (AZT) in the treatment of patients with AIDS and AIDS-related complex. N. Engl. J. Med. 1987, 317, 192-197.
    • Richman, D. D.; Fischl, M. A.; Grieco, M. H.; Gottlieb, M. S. Volherding, P. A.; Laskin, O. L.; Leedom, J. M.; Groopman, J. E. Mildvan, D.; Hirsch, M. S.; Jackson, G. G.; Durack, D. T.; Phil, D. Lusinoff-Lehrman, S. The AZT collaborative working group. The toxicity of azidothymidine (AZT) in the treatment of patients with AIDS and AIDS-related complex. N. Engl. J. Med. 1987, 317, 192-197.
  • 4
    • 0023143478 scopus 로고
    • Celluar, metabolism of 2′,3′- dideoxycytidine, a compound active against human immunodeficiency virus in vitro
    • Strames, M. C.; Cheng, Y. C. Celluar, metabolism of 2′,3′- dideoxycytidine, a compound active against human immunodeficiency virus in vitro. J. Biol. Chem. 1987, 252, 988-991.
    • (1987) J. Biol. Chem , vol.252 , pp. 988-991
    • Strames, M.C.1    Cheng, Y.C.2
  • 6
    • 0032490986 scopus 로고    scopus 로고
    • New development in the enantioselective synthesis of cyclopentyl carbocyclic nucleosides
    • Crimmins, M. T. New development in the enantioselective synthesis of cyclopentyl carbocyclic nucleosides. Tetrahedron 1998, 54, 9229-9272.
    • (1998) Tetrahedron , vol.54 , pp. 9229-9272
    • Crimmins, M.T.1
  • 7
    • 0032543455 scopus 로고    scopus 로고
    • Synthesis and anti-HIV activity of L-2′-fluoro-2′,3′-unsaturated purine nucleosides
    • Choi, Y.; Lee, K.; Hong, J. H.; Schinazi, R. F.; Chu, C. K. Synthesis and anti-HIV activity of L-2′-fluoro-2′,3′-unsaturated purine nucleosides. Tetrahedron Lett. 1998, 39, 4437-4440.
    • (1998) Tetrahedron Lett , vol.39 , pp. 4437-4440
    • Choi, Y.1    Lee, K.2    Hong, J.H.3    Schinazi, R.F.4    Chu, C.K.5
  • 8
    • 0033535597 scopus 로고    scopus 로고
    • Synthesis and anti-HIV and anti-HBV activities of 2′-fluoro-2′,3′-unsaturated L-nucleosides
    • Lee, K.; Choi, Y.; Gullen, E.; Schlueter-Wirtz, S.; Schinazi, R. F.; Cheng, Y.-C.; Chu, C. K. Synthesis and anti-HIV and anti-HBV activities of 2′-fluoro-2′,3′-unsaturated L-nucleosides. J. Med. Chem. 1999, 42, 1320-1328.
    • (1999) J. Med. Chem , vol.42 , pp. 1320-1328
    • Lee, K.1    Choi, Y.2    Gullen, E.3    Schlueter-Wirtz, S.4    Schinazi, R.F.5    Cheng, Y.-C.6    Chu, C.K.7
  • 9
    • 0037075785 scopus 로고    scopus 로고
    • Structure-activity relationships of 2′-fluoro-2′,3′- unsaturated D-nucleosides as anti-HIV agents
    • Lee, K.; Choi, Y.; Gumina, G.; Zhou, W.; Schinazi, R. F.; Chu, C. K. Structure-activity relationships of 2′-fluoro-2′,3′- unsaturated D-nucleosides as anti-HIV agents. J. Med. Chem. 2002, 45, 1313-1320.
    • (2002) J. Med. Chem , vol.45 , pp. 1313-1320
    • Lee, K.1    Choi, Y.2    Gumina, G.3    Zhou, W.4    Schinazi, R.F.5    Chu, C.K.6
  • 10
    • 0037168035 scopus 로고    scopus 로고
    • Stereoselective synthesis and antiviral activity of D-2′, 3′-didehydro-2′,3′-dideoxy-2′-fluoro-4′- thionucleosides
    • Chong, Y.; Choo, H.; Choi, Y.; Mathew, J.; Schinazi, R. F.; Chu, C. K. Stereoselective synthesis and antiviral activity of D-2′, 3′-didehydro-2′,3′-dideoxy-2′-fluoro-4′- thionucleosides. J. Med. Chem. 2002, 45, 4888-4898.
    • (2002) J. Med. Chem , vol.45 , pp. 4888-4898
    • Chong, Y.1    Choo, H.2    Choi, Y.3    Mathew, J.4    Schinazi, R.F.5    Chu, C.K.6
  • 11
    • 0037472859 scopus 로고    scopus 로고
    • Synthesis, anti-HIV activity and molecular mechanism of drug resistance of L-2′,3′-didehydro-2′,3′-dideoxy-2′- fluoro-4′-thionucleosides
    • Choo, H.; Chong, Y.; Choi, Y.; Mathew, J.; Schinazi, R. F.; Chu, C. K. Synthesis, anti-HIV activity and molecular mechanism of drug resistance of L-2′,3′-didehydro-2′,3′-dideoxy-2′- fluoro-4′-thionucleosides. J. Med. Chem. 2003, 46, 389-398.
    • (2003) J. Med. Chem , vol.46 , pp. 389-398
    • Choo, H.1    Chong, Y.2    Choi, Y.3    Mathew, J.4    Schinazi, R.F.5    Chu, C.K.6
  • 12
    • 1642388408 scopus 로고    scopus 로고
    • Synthesis, structure-activity relationships, and mechanism of drag resistance of D- and L-β-3′-fluoro-2′,3′- unsaturated-4′-thionucleosides as anti-HIV agents
    • Zhu, W.; Chong, Y.; Choo, H.; Mathews, J.; Schinazi, R. F.; Chu, C. K. Synthesis, structure-activity relationships, and mechanism of drag resistance of D- and L-β-3′-fluoro-2′,3′- unsaturated-4′-thionucleosides as anti-HIV agents. J. Med. Chem. 2004, 47, 1631-1640.
    • (2004) J. Med. Chem , vol.47 , pp. 1631-1640
    • Zhu, W.1    Chong, Y.2    Choo, H.3    Mathews, J.4    Schinazi, R.F.5    Chu, C.K.6
  • 13
    • 2942537776 scopus 로고    scopus 로고
    • Synthesis, structure-Activity relationships and drug resistance of β-L-3′-fluoro-2′,3′-unsaturated nucleosides as anti-HIV agents
    • Zhou, W.; Gumina, G.; Chong, Y.; Wang, J.: Schinazi, R. F.; Chu, C. K. Synthesis, structure-Activity relationships and drug resistance of β-L-3′-fluoro-2′,3′-unsaturated nucleosides as anti-HIV agents. J. Med Chem. 2004, 47, 3399-3408.
    • (2004) J. Med Chem , vol.47 , pp. 3399-3408
    • Zhou, W.1    Gumina, G.2    Chong, Y.3    Wang, J.4    Schinazi, R.F.5    Chu, C.K.6
  • 14
    • 20344368311 scopus 로고    scopus 로고
    • Synthesis, antiviral activity and mechanism of drag resistance of D- and L-2′,3′-didehydro-2′,3′-dideoxy-2′- fluoro-carbocyclic nucleosides
    • Wang, J.; Jin, Y. H.; Rapp, K. L.; Bennett, M.; Schinazi, R. F.; Chu, C. K. Synthesis, antiviral activity and mechanism of drag resistance of D- and L-2′,3′-didehydro-2′,3′-dideoxy-2′- fluoro-carbocyclic nucleosides. J. Med. Chem. 2005, 48, 3736-3748.
    • (2005) J. Med. Chem , vol.48 , pp. 3736-3748
    • Wang, J.1    Jin, Y.H.2    Rapp, K.L.3    Bennett, M.4    Schinazi, R.F.5    Chu, C.K.6
  • 15
    • 84985274539 scopus 로고    scopus 로고
    • Shealy, Y. F.; O'Dell, C. A.; Thorpe, M. C. carbocyclic analogues of thymidine nucleosides and related 1-substituted thymines. J. Heterocycl. Chem. 1981, 18, 383-389.
    • Shealy, Y. F.; O'Dell, C. A.; Thorpe, M. C. carbocyclic analogues of thymidine nucleosides and related 1-substituted thymines. J. Heterocycl. Chem. 1981, 18, 383-389.
  • 16
    • 1842461090 scopus 로고
    • Synthesis of the carbocyclic analogues of uracil nucleosides
    • Shealy, Y. F.; O'Dell, C. A. Synthesis of the carbocyclic analogues of uracil nucleosides. J. Heterocycl. Chem. 1976, 13, 1015-1020.
    • (1976) J. Heterocycl. Chem , vol.13 , pp. 1015-1020
    • Shealy, Y.F.1    O'Dell, C.A.2
  • 19
    • 0034947293 scopus 로고    scopus 로고
    • Increased drug susceptibility of HIV-1 reverse transcriptase mutants containing M184V and zidovudine-associated mutations: Analysis of enzyme processivity, chain-terminator removal and viral replication
    • Naeger, L. K.; Margot, N. A.; Miller, M. D.: Increased drug susceptibility of HIV-1 reverse transcriptase mutants containing M184V and zidovudine-associated mutations: analysis of enzyme processivity, chain-terminator removal and viral replication. Antiviral Res. 2001, 6, 115-126.
    • (2001) Antiviral Res , vol.6 , pp. 115-126
    • Naeger, L.K.1    Margot, N.A.2    Miller, M.D.3
  • 20
    • 0034616958 scopus 로고    scopus 로고
    • The role of steric hindrance in 3TC resistance of human immunodeficiency virus type-1 reverse transcriptase
    • (a) Gao, H.; Boyer, P. L.; Sarafianos, S. G.; Arnold, E.; Hughes, S. H. The role of steric hindrance in 3TC resistance of human immunodeficiency virus type-1 reverse transcriptase. J. Mol. Biol. 2000, 300, 403-418.
    • (2000) J. Mol. Biol , vol.300 , pp. 403-418
    • Gao, H.1    Boyer, P.L.2    Sarafianos, S.G.3    Arnold, E.4    Hughes, S.H.5
  • 21
    • 0034815271 scopus 로고    scopus 로고
    • Early detection of mixed mutations selected by antiretroviral agents in HIV-infected primary human lymphocytes
    • (b) Schinazi, R. F.; Schlueter-Wirtz, S.; Stuyver, L. Early detection of mixed mutations selected by antiretroviral agents in HIV-infected primary human lymphocytes. Antimicrob. Agents. Chemother. 2001, 12 (Suppl. 1), 61-65.
    • (2001) Antimicrob. Agents. Chemother , vol.12 , Issue.SUPPL. 1 , pp. 61-65
    • Schinazi, R.F.1    Schlueter-Wirtz, S.2    Stuyver, L.3
  • 23
    • 0027388895 scopus 로고
    • Evaluation of synergy between carbovir and 3′-azido-2′,3′-deoxythymidine for inhibition of human immunodeficiency virus type 1
    • Smith, M. S.; Kessler, J. A.; Rankin, C. D.; Pagano, J. S.; Kurtzberg, J.; Carter, S, G. Evaluation of synergy between carbovir and 3′-azido-2′,3′-deoxythymidine for inhibition of human immunodeficiency virus type 1. Antimicrob. Agents. Chemother. 1993, 37, 144-147.
    • (1993) Antimicrob. Agents. Chemother , vol.37 , pp. 144-147
    • Smith, M.S.1    Kessler, J.A.2    Rankin, C.D.3    Pagano, J.S.4    Kurtzberg, J.5    Carter, S.G.6
  • 25
    • 0034088720 scopus 로고    scopus 로고
    • Resistance profile of the human immunodeficiency virus type 1 reverse transcriptase inhibitor abacavir (1592U89) after monotherapy and combination therapy
    • Harrigan, P. R.; Stone, C.; Griffin, P.; Najera, I.; Bloor, S.; Kemp, S.; Tisdale, M.; Larder, B. Resistance profile of the human immunodeficiency virus type 1 reverse transcriptase inhibitor abacavir (1592U89) after monotherapy and combination therapy. J. Infect. Dis. 2000, 181, 912-920.
    • (2000) J. Infect. Dis , vol.181 , pp. 912-920
    • Harrigan, P.R.1    Stone, C.2    Griffin, P.3    Najera, I.4    Bloor, S.5    Kemp, S.6    Tisdale, M.7    Larder, B.8
  • 26
    • 0030945276 scopus 로고    scopus 로고
    • Combination of mutations in human immunodeficiency virus type 1 reverse transcriptase required for resistance to the carbocyclic nucleoside 1592U89
    • Tisdale, M.; Alnadaf, T.; Cousens, D. Combination of mutations in human immunodeficiency virus type 1 reverse transcriptase required for resistance to the carbocyclic nucleoside 1592U89. Antimicrob. Agents. Chemother. 1997, 41, 1094-1098.
    • (1997) Antimicrob. Agents. Chemother , vol.41 , pp. 1094-1098
    • Tisdale, M.1    Alnadaf, T.2    Cousens, D.3
  • 27
    • 0037161286 scopus 로고    scopus 로고
    • Insights into the molecular mechanism of inhibition and drug resistance for HIV-1 RT with carbovir triphosphate
    • Ray, A. S.; Yang, Z.; Shi, J.; Hobbs, A.; Schinazi, R. F.; Chu, C. K.; Anderson, K. S. Insights into the molecular mechanism of inhibition and drug resistance for HIV-1 RT with carbovir triphosphate. Biochemistry 2002, 41, 5150-5162.
    • (2002) Biochemistry , vol.41 , pp. 5150-5162
    • Ray, A.S.1    Yang, Z.2    Shi, J.3    Hobbs, A.4    Schinazi, R.F.5    Chu, C.K.6    Anderson, K.S.7
  • 28
    • 0033621167 scopus 로고    scopus 로고
    • Lamivudine (3TC) resistance in HIV-1 reverse transcriptase involves steric hindrance with β-branched amino acids
    • Sarafinos, S. G.; Das, K.; Clark, JR. A. D.; Ding, J.; Boyer, P. L.; Hughes, S. H.; Arnold, E. Lamivudine (3TC) resistance in HIV-1 reverse transcriptase involves steric hindrance with β-branched amino acids. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 10027-10032.
    • (1999) Proc. Natl. Acad. Sci. U.S.A , vol.96 , pp. 10027-10032
    • Sarafinos, S.G.1    Das, K.2    Clark, J.A.D.3    Ding, J.4    Boyer, P.L.5    Hughes, S.H.6    Arnold, E.7
  • 29
    • 0025362229 scopus 로고
    • Activity of 3′-azido-3′-deoxythymidine nucleotide dimers in primary lymphocytes infected with human immunodeficiency virus type 1
    • Schinazi, R. F.; Sommadossi, J. P.; Saalmann, V.; Cannon, D. L.; Xie, M. Y.; Hart, G. C.; Hahn, E. F. Activity of 3′-azido-3′-deoxythymidine nucleotide dimers in primary lymphocytes infected with human immunodeficiency virus type 1. Antimicrob. Agents. Chemother. 1990, 34, 1061-1067.
    • (1990) Antimicrob. Agents. Chemother , vol.34 , pp. 1061-1067
    • Schinazi, R.F.1    Sommadossi, J.P.2    Saalmann, V.3    Cannon, D.L.4    Xie, M.Y.5    Hart, G.C.6    Hahn, E.F.7
  • 31
    • 0032573488 scopus 로고    scopus 로고
    • Structure of a covalently trapped catalytic complex of HIV-1 reverse transcriptase: Implications for drug resistance
    • Huang, H.; Chopra, R.; Verdine, G. L.; Harrison, S. C. Structure of a covalently trapped catalytic complex of HIV-1 reverse transcriptase: Implications for drug resistance. Science 1998, 282, 1669-1675.
    • (1998) Science , vol.282 , pp. 1669-1675
    • Huang, H.1    Chopra, R.2    Verdine, G.L.3    Harrison, S.C.4
  • 32
    • 0029011701 scopus 로고    scopus 로고
    • Cornell, W. D.; Cieplak, P.; Bayly, C. I.; Gould, I. R.; Merz, K. M.; Ferguson, D. M.; Spellmeyer, D. C.; Fox, T.; Caldwell, J. W.; Kollman, P. A. A second generation force field for the simulation of proteins, nucleic acids, and organic molecules. J. Am. Chem. Soc. 1995, 117, 5179-5197.
    • (a) Cornell, W. D.; Cieplak, P.; Bayly, C. I.; Gould, I. R.; Merz, K. M.; Ferguson, D. M.; Spellmeyer, D. C.; Fox, T.; Caldwell, J. W.; Kollman, P. A. A second generation force field for the simulation of proteins, nucleic acids, and organic molecules. J. Am. Chem. Soc. 1995, 117, 5179-5197.
  • 33
    • 34247197491 scopus 로고    scopus 로고
    • (b) http://www.amber.uscf.edu/amber/Questions/fluorine.html.
  • 34
    • 0030937244 scopus 로고    scopus 로고
    • Organic fluorine hardly ever accepts hydrogen bonds
    • Dunitz, J. D.; Taylor, R. Organic fluorine hardly ever accepts hydrogen bonds. Chem. Eur. J. 1997, 3, 89-98.
    • (1997) Chem. Eur. J , vol.3 , pp. 89-98
    • Dunitz, J.D.1    Taylor, R.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.