메뉴 건너뛰기




Volumn 8, Issue 4, 1997, Pages 363-370

Structural features and anti-human immunodeficiency virus (HIV) activity of the isomers of 1-(2',6'-difluorophenyl)-1H,3H-thiazolo[3,4-a] benzimidazole, a potent non-nucleoside HIV-1 reverse transcriptase inhibitor

Author keywords

Absolute configuration; antiviral; HIV; NNRTI; TBZ; Thiazolobenzimidazole

Indexed keywords

9 CHLORO 4,5,6,7 TETRAHYDRO 5 METHYL 6 (3 METHYL 2 BUTENYL)IMIDAZO[4,5,1 JK][1,4]BENZODIAZEPINE 2(1H) THIONE; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; RNA DIRECTED DNA POLYMERASE INHIBITOR; ZALCITABINE; ZIDOVUDINE;

EID: 0030814399     PISSN: 09563202     EISSN: None     Source Type: Journal    
DOI: 10.1177/095632029700800409     Document Type: Article
Times cited : (46)

References (38)
  • 1
    • 0025859370 scopus 로고
    • Direct HPLC separation of thalidomide enantiomers using cellulose tris-4-methylphenyl benzoate chiral stationary phase
    • Aboul-Enein HY & Islam MR (1991) Direct HPLC separation of thalidomide enantiomers using cellulose tris-4-methylphenyl benzoate chiral stationary phase. Journal of Liquid Chromatograph 14: 667-673.
    • (1991) Journal of Liquid Chromatograph , vol.14 , pp. 667-673
    • Aboul-Enein, H.Y.1    Islam, M.R.2
  • 3
    • 0027363224 scopus 로고
    • Knocking-out concentrations of HIV-1-specific inhibitors completely suppress HIV-1 infection and prevent the emergence of drug-resistant virus
    • Balzarini J, Karlsson A, Pérez-Pérez M-J, Camarasa M-J & De Clercq E (1993a) Knocking-out concentrations of HIV-1-specific inhibitors completely suppress HIV-1 infection and prevent the emergence of drug-resistant virus. Virology 196: 576-585.
    • (1993) Virology , vol.196 , pp. 576-585
    • Balzarini, J.1    Karlsson, A.2    Pérez-Pérez, M.-J.3    Camarasa, M.-J.4    De Clercq, E.5
  • 4
    • 0027214433 scopus 로고
    • Treatment of human immunodeficiency virus type 1 (HIV-1)-infected cells with combinations of HIV-1-specific inhibitors results in a different resistance pattern than does treatment with single-drug therapy
    • Balzarini J, Karlsson A, Pérez-Pérez M-J, Camarasa M-J, Tarpley WG & De Clercq E (1993b) Treatment of human immunodeficiency virus type 1 (HIV-1)-infected cells with combinations of HIV-1-specific inhibitors results in a different resistance pattern than does treatment with single-drug therapy. Journal of Virology 67: 5353-5359.
    • (1993) Journal of Virology , vol.67 , pp. 5353-5359
    • Balzarini, J.1    Karlsson, A.2    Pérez-Pérez, M.-J.3    Camarasa, M.-J.4    Tarpley, W.G.5    De Clercq, E.6
  • 5
    • 0027328082 scopus 로고
    • HIV-1-specific reverse transcriptase inhibitors show differential activity against HIV-1 mutant strains containing different amino acid substitution in the reverse transcriptase
    • Balzarini J, Karlsson A, Pérez-Pérez M-J, Vrang L, Walbers J, Zhang H, Öberg B, Vandamme A-M, Camarasa M-J & De Clercq E (1993c) HIV-1-specific reverse transcriptase inhibitors show differential activity against HIV-1 mutant strains containing different amino acid substitution in the reverse transcriptase. Virology 192: 246-253.
    • (1993) Virology , vol.192 , pp. 246-253
    • Balzarini, J.1    Karlsson, A.2    Pérez-Pérez, M.-J.3    Vrang, L.4    Walbers, J.5    Zhang, H.6    Öberg, B.7    Vandamme, A.-M.8    Camarasa, M.-J.9    De Clercq, E.10
  • 6
    • 0027381149 scopus 로고
    • Human immunodeficiency virus type 1 drug-resistance patterns with different 1-[(2-hydroxyethoxy)-methyl]-6-(phenylthio)thymine derivatives
    • Balzarini J, Karlsson A & De Clercq E (1993d) Human immunodeficiency virus type 1 drug-resistance patterns with different 1-[(2-hydroxyethoxy)-methyl]-6-(phenylthio)thymine derivatives. Molecular Pharmacology 44: 694-701.
    • (1993) Molecular Pharmacology , vol.44 , pp. 694-701
    • Balzarini, J.1    Karlsson, A.2    De Clercq, E.3
  • 7
    • 0029989972 scopus 로고    scopus 로고
    • Activity of the (R)-enantiomers of 9-(2-phosphonylmethoxypropyl)-adenine and 9-(2-phosphonylmethoxypropyl)-2,6-diaminopurine against human immunodeficiency virus in different human cell systems
    • Balzarini J, Aquaro S, Perno C-F, Witvrouw M, Holy A & De Clercq E (1996) Activity of the (R)-enantiomers of 9-(2-phosphonylmethoxypropyl)-adenine and 9-(2-phosphonylmethoxypropyl)-2,6-diaminopurine against human immunodeficiency virus in different human cell systems. Biochemical and Biophysical Research Communications 219: 337-341.
    • (1996) Biochemical and Biophysical Research Communications , vol.219 , pp. 337-341
    • Balzarini, J.1    Aquaro, S.2    Perno, C.-F.3    Witvrouw, M.4    Holy, A.5    De Clercq, E.6
  • 8
    • 0041159796 scopus 로고
    • Least-squares absolute-structure refinement. Practical experience and ancillary calculations
    • Bernardinelli G & Flack HD (1985) Least-squares absolute-structure refinement. Practical experience and ancillary calculations. Acta Crystallographica Section A 41: 500-511.
    • (1985) Acta Crystallographica Section A , vol.41 , pp. 500-511
    • Bernardinelli, G.1    Flack, H.D.2
  • 11
    • 0026324187 scopus 로고
    • Anti-HIV agents I: Synthesis and in vitro anti-HIV evaluation of novel 1H,3H-thiazolo[3,4-a]benzimidazoles
    • Chimirri A, Grasso S, Monforte AM, Monforte P & Zappalà M (1991a) Anti-HIV agents I: synthesis and in vitro anti-HIV evaluation of novel 1H,3H-thiazolo[3,4-a]benzimidazoles. Il Farmaco 46: 817-823.
    • (1991) Il Farmaco , vol.46 , pp. 817-823
    • Chimirri, A.1    Grasso, S.2    Monforte, A.M.3    Monforte, P.4    Zappalà, M.5
  • 12
    • 0025812546 scopus 로고
    • Anti-HIV agents II: Synthesis and in vitro anti-HIV activity of novel 1H,3H-thiazolo[3,4-a]benzimidazoles
    • Chimirri A, Grasso S, Monforte AM, Monforte P & Zappalà M (1991b) Anti-HIV agents II: synthesis and in vitro anti-HIV activity of novel 1H,3H-thiazolo[3,4-a]benzimidazoles. Il Farmaco 46: 925-933.
    • (1991) Il Farmaco , vol.46 , pp. 925-933
    • Chimirri, A.1    Grasso, S.2    Monforte, A.M.3    Monforte, P.4    Zappalà, M.5
  • 13
    • 0028145135 scopus 로고
    • Anti-HIV agents III: Synthesis and in vitro anti-HIV activity of novel 1H,3H-thiazolo[3,4-a]imidazo[4,5-b]pyridines
    • Chimirri A, Grasso S, Monforte AM, Monforte P & Zappalà M (1994) Anti-HIV agents III: synthesis and in vitro anti-HIV activity of novel 1H,3H-thiazolo[3,4-a]imidazo[4,5-b]pyridines. Il Farmaco 49: 345-348.
    • (1994) Il Farmaco , vol.49 , pp. 345-348
    • Chimirri, A.1    Grasso, S.2    Monforte, A.M.3    Monforte, P.4    Zappalà, M.5
  • 14
    • 0030057371 scopus 로고    scopus 로고
    • Anti-HIV agents IV: Synthesis and in vitro anti-HIV activity of novel 1-(2,6-difluorophenyl)-1H,3H-thiazolo[3,4-a]benzimidazoles
    • Chimirri A, Grasso S, Molica C, Monforte AM, Monforte P & Zappalà M (1996) Anti-HIV agents IV: synthesis and in vitro anti-HIV activity of novel 1-(2,6-difluorophenyl)-1H,3H-thiazolo[3,4-a]benzimidazoles. Il Farmaco 51: 279-282.
    • (1996) Il Farmaco , vol.51 , pp. 279-282
    • Chimirri, A.1    Grasso, S.2    Molica, C.3    Monforte, A.M.4    Monforte, P.5    Zappalà, M.6
  • 16
    • 0027447133 scopus 로고
    • HIV-1-specific RT inhibitors: Highly selective inhibitors of human immunodeficiency virus type 1 that are specifically targeted at the viral reverse transcriptase
    • De Clercq E (1993) HIV-1-specific RT inhibitors: highly selective inhibitors of human immunodeficiency virus type 1 that are specifically targeted at the viral reverse transcriptase. Medicinal Research Reviews 13: 229-258.
    • (1993) Medicinal Research Reviews , vol.13 , pp. 229-258
    • De Clercq, E.1
  • 17
    • 0028325491 scopus 로고
    • Non-nucleoside reverse transcriptase inhibitors (NNRTIs)
    • De Clercq E (1994a) Non-nucleoside reverse transcriptase inhibitors (NNRTIs). Expert Opinions in Investigational Drugs 3: 253-271.
    • (1994) Expert Opinions in Investigational Drugs , vol.3 , pp. 253-271
    • De Clercq, E.1
  • 18
    • 0028120730 scopus 로고
    • HIV resistance to reverse transcriptase inhibitors
    • De Clercq E (1994b) HIV resistance to reverse transcriptase inhibitors. Biochemical Pharmacology 47: 155-169.
    • (1994) Biochemical Pharmacology , vol.47 , pp. 155-169
    • De Clercq, E.1
  • 19
    • 0028941196 scopus 로고
    • Antiviral therapy of human immunodeficiency virus infections
    • De Clercq E (1995a) Antiviral therapy of human immunodeficiency virus infections. Clinical Microbiology Reviews 8: 200-239.
    • (1995) Clinical Microbiology Reviews , vol.8 , pp. 200-239
    • De Clercq, E.1
  • 20
    • 0029011730 scopus 로고
    • Toward improved anti-HIV chemotherapy: Therapeutic strategies for intervention with HIV infections
    • De Clercq E (1995b) 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
    • 0029593364 scopus 로고
    • Knocking out human immunodeficiency virus through non-nucleoside reverse transcriptase inhibitors used as single agents or in combination: A paradigm for the cure of AIDS
    • De Clercq E & Balzarini J (1995) Knocking out human immunodeficiency virus through non-nucleoside reverse transcriptase inhibitors used as single agents or in combination: a paradigm for the cure of AIDS. Il Farmaco 50: 735-747.
    • (1995) Il Farmaco , vol.50 , pp. 735-747
    • De Clercq, E.1    Balzarini, J.2
  • 22
    • 0014461331 scopus 로고
    • Profile analysis in single crystal diffractometry
    • Diamond R (1969) Profile analysis in single crystal diffractometry. Acta Crystallographica Section A 25: 43-55.
    • (1969) Acta Crystallographica Section A , vol.25 , pp. 43-55
    • Diamond, R.1
  • 26
    • 0027225174 scopus 로고
    • Specific inhibition of the reverse transcriptase of human immunodeficiency virus type 1 and the chimeric enzymes of human immunodeficiency virus type 1 and type 2 by nonnucleoside inhibitors
    • Hizi A, Tal R, Shaharabany M, Currens MJ, Boyd MR, Hughes SH & McMahon JB (1993) Specific inhibition of the reverse transcriptase of human immunodeficiency virus type 1 and the chimeric enzymes of human immunodeficiency virus type 1 and type 2 by nonnucleoside inhibitors. Antimicrobial Agents and Chemotherapy 37: 1037-1042.
    • (1993) Antimicrobial Agents and Chemotherapy , vol.37 , pp. 1037-1042
    • Hizi, A.1    Tal, R.2    Shaharabany, M.3    Currens, M.J.4    Boyd, M.R.5    Hughes, S.H.6    McMahon, J.B.7
  • 28
    • 84980087363 scopus 로고
    • A method of absorption correction by X-ray intensity measurements
    • Kopfmann G & Huber R (1968) A method of absorption correction by X-ray intensity measurements. Acta Crystallographica Section A 24: 348-351.
    • (1968) Acta Crystallographica Section A , vol.24 , pp. 348-351
    • Kopfmann, G.1    Huber, R.2
  • 29
    • 0020909036 scopus 로고
    • PARST: A system of FORTRAN routines for calculating molecular structure parameters from results of crystal structure analyses
    • Nardelli M (1983) PARST: a system of FORTRAN routines for calculating molecular structure parameters from results of crystal structure analyses. Computational Chemistry 7: 95-98.
    • (1983) Computational Chemistry , vol.7 , pp. 95-98
    • Nardelli, M.1
  • 31
    • 0000804347 scopus 로고
    • Competitive inhibitors of human immunodeficiency virus reverse transcriptase
    • Schinazi RF (1993) Competitive inhibitors of human immunodeficiency virus reverse transcriptase. Perspectives on Drug Discovery and Design 1: 151-180.
    • (1993) Perspectives on Drug Discovery and Design , vol.1 , pp. 151-180
    • Schinazi, R.F.1
  • 35
    • 84943920736 scopus 로고
    • Phase annealing in SHELX-90: Direct methods for larger structures
    • Sheldrick GM (1990b) Phase annealing in SHELX-90: direct methods for larger structures. Acta Crystallographica Section A 46: 467-473.
    • (1990) Acta Crystallographica Section A , vol.46 , pp. 467-473
    • Sheldrick, G.M.1
  • 37
    • 0027177561 scopus 로고
    • Solubilization of thiazolobenzimidazole using a combination of pH adjustment and complexation with 2-hydroxypropyl-β cyclodextrin
    • Tinwalla AY, Hoesterey BL, Xiang T & Anderson BD (1993) Solubilization of thiazolobenzimidazole using a combination of pH adjustment and complexation with 2-hydroxypropyl-β cyclodextrin. Pharmaceutical Research 10: 1136-1143.
    • (1993) Pharmaceutical Research , vol.10 , pp. 1136-1143
    • Tinwalla, A.Y.1    Hoesterey, B.L.2    Xiang, T.3    Anderson, B.D.4
  • 38
    • 0024578841 scopus 로고
    • New soluble-formazan assay for HIV-1 cytopathic effects: Application to high-flux screening of synthetic and natural products for AIDS-antiviral activity
    • Weislow OS, Kiser R, Fine DL, Bader J, Shoemaker RH & Boyd MR (1989) New soluble-formazan assay for HIV-1 cytopathic effects: application to high-flux screening of synthetic and natural products for AIDS-antiviral activity. Journal of the National Cancer Institute 81: 577-586.
    • (1989) Journal of the National Cancer Institute , vol.81 , pp. 577-586
    • Weislow, O.S.1    Kiser, R.2    Fine, D.L.3    Bader, J.4    Shoemaker, R.H.5    Boyd, M.R.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.