메뉴 건너뛰기




Volumn 14, Issue 5, 2003, Pages 249-262

Structure-activity relationship studies on a novel family of specific HIV-1 reverse transcriptase inhibitors

Author keywords

AIDS; HIV; N 3 carboxymethyl TBDMS substituted nucleosides; NNRTI; Non nucleoside reverse transcriptase inhibitors

Indexed keywords

1 [2',5' BIS O (TERT BUTYLDIMETHYLSILYL) BETA DEXTRO RIBOFURANOSYL] 2 N [(CARBOXY)METHYL]THYMINE; 2',5' BIS O (TERT BUTYLDIMETHYLSILYL) 1 N [(CARBOXY)METHYL]INOSINE; 3',5' BIS O (TERT BUTYLDIMETHYLSILYL) 1 N [(CARBOXY)METHYL]INOSINE; DIDANOSINE; HYPOXANTHINE DERIVATIVE; NEW DRUG; NUCLEOSIDE DERIVATIVE; RNA DIRECTED DNA POLYMERASE INHIBITOR; STAVUDINE; UNCLASSIFIED DRUG; ZIDOVUDINE;

EID: 0345098561     PISSN: 09563202     EISSN: None     Source Type: Journal    
DOI: 10.1177/095632020301400504     Document Type: Article
Times cited : (5)

References (40)
  • 2
    • 0029977510 scopus 로고    scopus 로고
    • Targeting HIV reverse transcriptase for anti-AIDS drug design: Structural and biological considerations for chemotherapeutic strategies
    • Arnold E, Das K, Ding J, Yadav PN, Hsiou Y, Boyer PL, Hughes SH (1996) Targeting HIV reverse transcriptase for anti-AIDS drug design: structural and biological considerations for chemotherapeutic strategies. Drug Design & Discovery 13: 29-47
    • (1996) Drug Design & Discovery , vol.13 , pp. 29-47
    • Arnold, E.1    Das, K.2    Ding, J.3    Yadav, P.N.4    Hsiou, Y.5    Boyer, P.L.6    Hughes, S.H.7
  • 3
    • 0030868897 scopus 로고    scopus 로고
    • Positive effects of combined antiretroviral therapy on CD4 (+)T cell homeostasis and function in advanced HIV disease
    • Autran B, Carcelain G, Li TS, Blanc C, Mathez D, Tubiana R, Katlama C, Debre, P & Leibowitch J (1997) Positive effects of combined antiretroviral therapy on CD4 (+)T cell homeostasis and function in advanced HIV disease. Science 277: 112-116.
    • (1997) Science , vol.277 , pp. 112-116
    • Autran, B.1    Carcelain, G.2    Li, T.S.3    Blanc, C.4    Mathez, D.5    Tubiana, R.6    Katlama, C.7    Debre, P.8    Leibowitch, J.9
  • 5
    • 0026606044 scopus 로고
    • 2′,5′-Bis-O-(tert-butyldimethylsilyl)-3′-spiro-5″ -(4″-amino-1″,2″-oxathiole-2″,2″-dioxide) pyrimidine (TSAO) nucleoside analogues: Highly selective inhibitors of human immunodeficiency virus type 1 that are targeted at the viral reverse transcriptase
    • Balzaríni J, Pérez-Pérez MJ, San-Félix A, Schols D, Perno CF, Vandamme AM, Camarasa MJ & De Clercq E (1992a) 2′,5′-Bis-O-(tert-butyldimethylsilyl)-3′-spiro-5″ -(4″-amino-1″,2″-oxathiole-2″,2″-dioxide) pyrimidine (TSAO) nucleoside analogues: highly selective inhibitors of human immunodeficiency virus type 1 that are targeted at the viral reverse transcriptase. Proceedings of the National Academy of Sciences, USA 89: 4392-4396.
    • (1992) Proceedings of the National Academy of Sciences, USA , vol.89 , pp. 4392-4396
    • Balzaríni, J.1    Pérez-Pérez, M.J.2    San-Félix, A.3    Schols, D.4    Perno, C.F.5    Vandamme, A.M.6    Camarasa, M.J.7    De Clercq, E.8
  • 6
    • 0026724892 scopus 로고
    • Kinetics of inhibition of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase by the novel HIV-1-specific nucleoside analogue [2′,5′-Bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl] -3′-spiro-5″-(4″-amino-1″,2″-oxathiole-2″, 2″-dioxide) thymine (TSAO-T)
    • Balzarini J, Pérez-Pérez MJ, San-Félix A, Camarasa MJ, Bathurst IC, Barr PJ & De Clercq E (1992b) Kinetics of inhibition of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase by the novel HIV-1-specific nucleoside analogue [2′,5′ -Bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3′-spiro-5″ -(4″-amino-1″,2″-oxathiole-2″,2″-dioxide) thymine (TSAO-T). Journal of Biological Chemistry 267: 11831-11838.
    • (1992) Journal of Biological Chemistry , vol.267 , pp. 11831-11838
    • Balzarini, J.1    Pérez-Pérez, M.J.2    San-Félix, A.3    Camarasa, M.J.4    Bathurst, I.C.5    Barr, P.J.6    De Clercq, E.7
  • 8
    • 0030831665 scopus 로고    scopus 로고
    • Changing incidence of AIDS-defining illnesses in the era of antiretroviral combination therapy
    • Brodt HR, Kamps BS, Gute P, Knupp B, Staszewski S & Helm EB (1997) Changing incidence of AIDS-defining illnesses in the era of antiretroviral combination therapy. AIDS 11: 1731-1738.
    • (1997) AIDS , vol.11 , pp. 1731-1738
    • Brodt, H.R.1    Kamps, B.S.2    Gute, P.3    Knupp, B.4    Staszewski, S.5    Helm, E.B.6
  • 9
    • 0033490797 scopus 로고    scopus 로고
    • Synthesis and anti-HIV-evaluation of 2′,3′-dideoxyimidazo- and v-triazolo[4,5-d]pyridazine nucleosides
    • Bussolari JC & Panzica RP (1999) Synthesis and anti-HIV-evaluation of 2′,3′-dideoxyimidazo- and v-triazolo[4,5-d]pyridazine nucleosides. Bioorganic & Medicinal Chemistry 7: 2373-2379.
    • (1999) Bioorganic & Medicinal Chemistry , vol.7 , pp. 2373-2379
    • Bussolari, J.C.1    Panzica, R.P.2
  • 11
    • 0026771409 scopus 로고
    • 3′-Spiro nucleosides, a new class of specific human immunodeficiency virus type 1 inhibitors: Synthesis and antiviral activity of [2′,5′-Bis-O-(tert-butyldimethylsilyl)-β-D-xylo-and -ribofuranose]-3″-spiro-5″-(4″-amino-1″, 2″-oxathiole-2″,2″-dioxide) (TSAO)pyrimidine nucleosides
    • Camarasa MJ, Pérez-Pérez MJ, San-Félix A, Balzarini J & De Clercq E (1992) 3′-Spiro nucleosides, a new class of specific human immunodeficiency virus type 1 inhibitors: synthesis and antiviral activity of [2′,5′-Bis-O-(tert-butyldimethylsilyl) -β-D-xylo-and -ribofuranose]-3″-spiro-5″-(4″ -amino-1″,2″-oxathiole-2″,2″-dioxide) (TSAO)pyrimidine nucleosides. Journal of Medicinal Chemistry 35: 2721-2727.
    • (1992) Journal of Medicinal Chemistry , vol.35 , pp. 2721-2727
    • Camarasa, M.J.1    Pérez-Pérez, M.J.2    San-Félix, A.3    Balzarini, J.4    De Clercq, E.5
  • 13
    • 0032493043 scopus 로고    scopus 로고
    • A syndrome of peripheral lipodystrophy, hyperlipidaemia and insulin resistance in patients receiving HIV protease inhibitors
    • Carr A, Samaras K, Burton S, Law M, Freund J, Chisholm DJ & Cooper DA (1998) A syndrome of peripheral lipodystrophy, hyperlipidaemia and insulin resistance in patients receiving HIV protease inhibitors. AIDS 12: F51-F58.
    • (1998) AIDS , vol.12
    • Carr, A.1    Samaras, K.2    Burton, S.3    Law, M.4    Freund, J.5    Chisholm, D.J.6    Cooper, D.A.7
  • 17
    • 0023796219 scopus 로고
    • An efficient total synthesis of 3′-azido-3′-deoxythymidine (AZT) and 3′-azido-2′,3′-dideoxyuridine (AZDDU, CS-87) from D-mannitol
    • Chu C, Warren Beach J, Ullas V & Kosugi Y (1988) An efficient total synthesis of 3′-azido-3′-deoxythymidine (AZT) and 3′-azido-2′,3′-dideoxyuridine (AZDDU, CS-87) from D-mannitol. Tetrahedron Letters 29: 5349-5352.
    • (1988) Tetrahedron Letters , vol.29 , pp. 5349-5352
    • Chu, C.1    Warren Beach, J.2    Ullas, V.3    Kosugi, Y.4
  • 18
    • 0343471516 scopus 로고    scopus 로고
    • Urinary stones in HIV-1-positive patients treated with indinavir
    • Daudon M, Estepa L, Viard JP, Joly D & Jungers P (1997) Urinary stones in HIV-1-positive patients treated with indinavir. Lancet 349:1294-1295.
    • (1997) Lancet , vol.349 , pp. 1294-1295
    • Daudon, M.1    Estepa, L.2    Viard, J.P.3    Joly, D.4    Jungers, P.5
  • 19
    • 0032437454 scopus 로고    scopus 로고
    • The role of non-nucleoside reverse transcriptase inhibitors (NNRTIs) in the therapy of HIV-1 infection
    • De Clercq E (1998) The role of non-nucleoside reverse transcriptase inhibitors (NNRTIs) in the therapy of HIV-1 infection. Antiviral Research 38: 153-179.
    • (1998) Antiviral Research , vol.38 , pp. 153-179
    • De Clercq, E.1
  • 20
    • 0029011730 scopus 로고
    • Toward improved anti-HIV chemotherapy: Therapeutic strategies for intervention with HIV infections
    • De Clercq E (1995) Toward improved anti-HIV chemotherapy: therapeutic strategies for intervention with HIV infections. Journal of Medicinal Chemistry 38: 2491-2517.
    • (1995) Journal of Medicinal Chemistry , vol.38 , pp. 2491-2517
    • De Clercq, E.1
  • 21
    • 0030708683 scopus 로고    scopus 로고
    • In search of a selective antiviral chemotherapy
    • De Clercq E (1997) In search of a selective antiviral chemotherapy. Clinical & Microbiology Reviews 10: 674-693.
    • (1997) Clinical & Microbiology Reviews , vol.10 , pp. 674-693
    • De Clercq, E.1
  • 23
    • 0036836947 scopus 로고    scopus 로고
    • 5-Substituted-1H-tetrazoles as carboxylic isosteres: Medicinal chemistry and synthetic methods
    • Herr RJ (2002) 5-Substituted-1H-tetrazoles as carboxylic isosteres: medicinal chemistry and synthetic methods. Bioorganic & Medicinal Chemistry 10: 3379-3393.
    • (2002) Bioorganic & Medicinal Chemistry , vol.10 , pp. 3379-3393
    • Herr, R.J.1
  • 24
    • 0034059835 scopus 로고    scopus 로고
    • The HIV-1 reverse transcription (RT) process as target for RT inhibitors
    • Jonckheere H, Anné J & De Clercq E (2000) The HIV-1 reverse transcription (RT) process as target for RT inhibitors. Medicinal Research Reviews 20: 129-154.
    • (2000) Medicinal Research Reviews , vol.20 , pp. 129-154
    • Jonckheere, H.1    Anné, J.2    De Clercq, E.3
  • 25
    • 0028099251 scopus 로고
    • Resistance of HIV-1 reverse transcriptase against [2′,5′ -Bis-O-(tert-butyldimethylsilyl)-3′-spiro-5″-(4″ -amino-1″,2″-oxathiole-2″,2″-dioxide)] (TSAO) derivatives is determined by the mutation Glu138Lys on the p51 subunit
    • Jonckheere H, Taymans JM, Balzarini J, Velázquez S, Camarasa MJ, Desmyter J, De Clercq E & Anné J (1994) Resistance of HIV-1 reverse transcriptase against [2′,5′ -Bis-O-(tert-butyldimethylsilyl)-3′-spiro-5″-(4″ -amino-1″,2″-oxathiole-2″,2″-dioxide)] (TSAO) derivatives is determined by the mutation Glu138Lys on the p51 subunit. Journal of Biological Chemistry 269: 25255-25258.
    • (1994) Journal of Biological Chemistry , vol.269 , pp. 25255-25258
    • Jonckheere, H.1    Taymans, J.M.2    Balzarini, J.3    Velázquez, S.4    Camarasa, M.J.5    Desmyter, J.6    De Clercq, E.7    Anné, J.8
  • 27
    • 0032492398 scopus 로고    scopus 로고
    • CD4-cell count in HIV-1-infected individuals remaining viraemic with highly active antiretroviral therapy (HAART). Swiss HIV Cohort Study
    • Kaufmann D, Pantaleo G, Sudre P & Telenti A (1998) CD4-cell count in HIV-1-infected individuals remaining viraemic with highly active antiretroviral therapy (HAART). Swiss HIV Cohort Study. Lancet 351: 723-724.
    • (1998) Lancet , vol.351 , pp. 723-724
    • Kaufmann, D.1    Pantaleo, G.2    Sudre, P.3    Telenti, A.4
  • 28
    • 0033797517 scopus 로고    scopus 로고
    • A new inosine disaccharide from the crustacean ligia exotica: Isolation and structure elucidation by total synthesis
    • Kim SH, Yoo S-M, Park IS & Kim YH (2000) A new inosine disaccharide from the crustacean ligia exotica: isolation and structure elucidation by total synthesis. Journal of Natural Products 63:1188-1191.
    • (2000) Journal of Natural Products , vol.63 , pp. 1188-1191
    • Kim, S.H.1    Yoo, S.-M.2    Park, I.S.3    Kim, Y.H.4
  • 29
    • 0001756111 scopus 로고
    • The synthesis of oligoribonucleotides. II. The use of silyl protecting groups in nucleoside and nucleotide chemistry. VII
    • Ogilvie KK, Beaucage SL, Shifman AL, Theriault NY & Sadana K (1978) The synthesis of oligoribonucleotides. II. The use of silyl protecting groups in nucleoside and nucleotide chemistry. VII. Canadian Journal of Chemistry 56: 2768-2780.
    • (1978) Canadian Journal of Chemistry , vol.56 , pp. 2768-2780
    • Ogilvie, K.K.1    Beaucage, S.L.2    Shifman, A.L.3    Theriault, N.Y.4    Sadana, K.5
  • 30
    • 33751500481 scopus 로고
    • Novel template effects of distannoxane catalysts in highly efficient transesterification and esterification
    • Otera J, Dan-oh N & Nozaki H (1991) novel template effects of distannoxane catalysts in highly efficient transesterification and esterification Journal of Organic Chemistry 56: 5307-5311.
    • (1991) Journal of Organic Chemistry , vol.56 , pp. 5307-5311
    • Otera, J.1    Dan-Oh, N.2    Nozaki, H.3
  • 31
    • 7744243992 scopus 로고    scopus 로고
    • Bioisosterism: A rational approach in drug design
    • Patani GA & LaVoie EJ (1996) Bioisosterism: a rational approach in drug design. Chemical Reviews 96: 3147-3176.
    • (1996) Chemical Reviews , vol.96 , pp. 3147-3176
    • Patani, G.A.1    LaVoie, E.J.2
  • 33
    • 0026737678 scopus 로고
    • TSAO-analogues. Stereospecific synthesis and anti-HIV-1 activity of 1-[2′,5′-Bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl] -3′-spiro-5″-(4″-amino-1″,2″-oxathiole-2″, 2″-dioxide) pyrimidine and pyrimidine-modified nucleosides
    • Pérez-Pérez MJ, San-Félix A, Balzarini J, De Clercq E & Camarasa MJ (1992) TSAO-analogues. Stereospecific synthesis and anti-HIV-1 activity of 1-[2′,5′ -Bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3′-spiro-5″ -(4″-amino-1″,2″-oxathiole-2″,2″-dioxide) pyrimidine and pyrimidine-modified nucleosides. Journal of Medicinal Chemistry 35: 2988-2995.
    • (1992) Journal of Medicinal Chemistry , vol.35 , pp. 2988-2995
    • Pérez-Pérez, M.J.1    San-Félix, A.2    Balzarini, J.3    De Clercq, E.4    Camarasa, M.J.5
  • 34
    • 0032547101 scopus 로고    scopus 로고
    • HIV treatment failure: Testing for HIV resistance in clinical practice
    • Perrin L & Telenti A (1998) HIV treatment failure: testing for HIV resistance in clinical practice. Science 280: 1871-1873.
    • (1998) Science , vol.280 , pp. 1871-1873
    • Perrin, L.1    Telenti, A.2
  • 36
    • 0033038485 scopus 로고    scopus 로고
    • HIV-1 and HAART: A time to cure, a time to kill
    • Saag MS & Kilby JM (1997) HIV-1 and HAART: a time to cure, a time to kill. Nature Medicine 5: 609-611.
    • (1997) Nature Medicine , vol.5 , pp. 609-611
    • Saag, M.S.1    Kilby, J.M.2
  • 37
    • 0000804347 scopus 로고
    • Competitive inhibitors of human immunodeficiency virus reverse transcriptase
    • Schinazi RF (1993) Competitive inhibitors of human immunodeficiency virus reverse transcriptase. Perspective in Drug Discovery 1: 151-180.
    • (1993) Perspective in Drug Discovery , vol.1 , pp. 151-180
    • Schinazi, R.F.1
  • 38
    • 0345383591 scopus 로고
    • Unnatural nucleosides and nucleotides. IV. Preparation of 5-alkyluridines and their 5′-mono-and triphosphates
    • Szemzö A, Szabolcs A, Sági J & Ötvös L (1980) Unnatural nucleosides and nucleotides. IV. Preparation of 5-alkyluridines and their 5′-mono-and triphosphates. Journal Carbohydrates, Nucleosides & Nucleotides 7: 365-379.
    • (1980) Journal Carbohydrates, Nucleosides & Nucleotides , vol.7 , pp. 365-379
    • Szemzö, A.1    Szabolcs, A.2    Sági, J.3    Ötvös, L.4
  • 39
    • 0036629967 scopus 로고    scopus 로고
    • Immune restoration after treatment of HIV-1 infection with highly active antiretroviral therapy (HAART)
    • Valdez H (2002) Immune restoration after treatment of HIV-1 infection with highly active antiretroviral therapy (HAART). AIDS Reviews 4: 157-164.
    • (2002) AIDS Reviews , vol.4 , pp. 157-164
    • Valdez, H.1
  • 40
    • 0029925584 scopus 로고    scopus 로고
    • 13C NMR spectral characteristics of 8-bromo-2′,3′-dideoxyguanosine and 8-bromo-2′,3′-dideoxyinosine
    • 13C NMR spectral characteristics of 8-bromo-2′,3′ -dideoxyguanosine and 8-bromo-2′,3′-dideoxyinosine. Nucleosides & Nucleotides 15: 1077-1096.
    • (1996) Nucleosides & Nucleotides , vol.15 , pp. 1077-1096
    • Zeidler, J.1    Golankiewicz, B.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.