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Volumn 39, Issue 20, 1996, Pages 4109-4115

Neighboring group catalysis in the design of nucleotide prodrugs

Author keywords

[No Author keywords available]

Indexed keywords

2',3' DIDEOXYTHYMIDINE; ESTERASE; NUCLEOTIDE DERIVATIVE; PHOSPHORUS ACID DERIVATIVE; PRODRUG; SALICYLIC ACID DERIVATIVE; ZIDOVUDINE DERIVATIVE;

EID: 0029796135     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9600757     Document Type: Article
Times cited : (8)

References (23)
  • 2
    • 0022592073 scopus 로고
    • Commentary: Metabolic impediments to the use of nucleotide derivatives to circumvent resistance to purine and pyrimidine analogs
    • Bennet, L. L.; Brockmann, R. W.; Montgomery, J. A. Commentary: metabolic impediments to the use of nucleotide derivatives to circumvent resistance to purine and pyrimidine analogs. Nucleosides Nucleotides 1986, 5, 117-124.
    • (1986) Nucleosides Nucleotides , vol.5 , pp. 117-124
    • Bennet, L.L.1    Brockmann, R.W.2    Montgomery, J.A.3
  • 3
    • 0026710273 scopus 로고
    • Potential prodrug derivatives of 2′,3′-didehydro-2′,3′-dideoxynucleosides. Preparations and antiviral activities
    • Mullah, K. B.; Rao, T. S.; Balzarini, J.; De Clercq, E.; Bentrude, W. G. Potential prodrug derivatives of 2′,3′-didehydro-2′,3′-dideoxynucleosides. Preparations and antiviral activities. J. Med. Chem. 1992, 35, 2728-2735.
    • (1992) J. Med. Chem. , vol.35 , pp. 2728-2735
    • Mullah, K.B.1    Rao, T.S.2    Balzarini, J.3    De Clercq, E.4    Bentrude, W.G.5
  • 4
    • 0026524003 scopus 로고
    • Membrane-permeable dideoxyuridine 5′-monophosphate analogue inhibits human immunodeficiency virus replication
    • Sastry, J. K.; Nehete, P. N.; Khan, S.; Nowak, B. J.; Plankett, W.; Arlinghaus, R. B.; Farquhar, D. Membrane-permeable dideoxyuridine 5′-monophosphate analogue inhibits human immunodeficiency virus replication. Mol. Pharmacol. 1992, 41, 441-445.
    • (1992) Mol. Pharmacol. , vol.41 , pp. 441-445
    • Sastry, J.K.1    Nehete, P.N.2    Khan, S.3    Nowak, B.J.4    Plankett, W.5    Arlinghaus, R.B.6    Farquhar, D.7
  • 5
    • 0023915671 scopus 로고
    • AIDS Dementia: Synthesis and properties of a derivative of 3′-azido-3′-deoxythymidine (AZT) that may become "locked" in the central nervous system
    • Torrence, P. F.; Kinjo, J.; Lesiak, K.; Balzarini, J.; De Clercq, E. AIDS Dementia: synthesis and properties of a derivative of 3′-azido-3′-deoxythymidine (AZT) that may become "locked" in the central nervous system. FEBS Lett. 1988, 234, 135-140.
    • (1988) FEBS Lett. , vol.234 , pp. 135-140
    • Torrence, P.F.1    Kinjo, J.2    Lesiak, K.3    Balzarini, J.4    De Clercq, E.5
  • 6
    • 0024500236 scopus 로고
    • A dihydropyridine carrier system for sustained delivery of 2′,3′-dideoxynucleosides to the brain
    • Palomino, E.; Kessel, D.; Horwitz, J. P. J. A dihydropyridine carrier system for sustained delivery of 2′,3′-dideoxynucleosides to the brain. J. Med. Chem. 1989, 32, 622-625.
    • (1989) J. Med. Chem. , vol.32 , pp. 622-625
    • Palomino, E.1    Kessel, D.2    Horwitz, J.P.J.3
  • 7
    • 0025290649 scopus 로고
    • Brain targeting of anti-HIV nucleosides: Synthesis and in vitro and in vivo studies of dihydropyridine derivatives of 3′-azido-2′,3′-dideoxyuridines and 3′-azido, 3′-deoxythymidine
    • Chu, C. K.; Bhadti, V. S.; Doshi, K. J.; Etse, J. T.; Gallo, J. M.; Boudinot, F. D.; Schinazi, R. F. Brain targeting of anti-HIV nucleosides: synthesis and in vitro and in vivo studies of dihydropyridine derivatives of 3′-azido-2′,3′-dideoxyuridines and 3′-azido, 3′-deoxythymidine. J. Med. Chem. 1990, 33, 2188-2192.
    • (1990) J. Med. Chem. , vol.33 , pp. 2188-2192
    • Chu, C.K.1    Bhadti, V.S.2    Doshi, K.J.3    Etse, J.T.4    Gallo, J.M.5    Boudinot, F.D.6    Schinazi, R.F.7
  • 9
    • 0025992331 scopus 로고
    • Brain, blood, and cerebrospinal fluid distribution of a Zidovudine chemical delivery system in rabbits
    • Brewster, M. E.; Anderson, W.; Bodor, N. Brain, blood, and cerebrospinal fluid distribution of a Zidovudine chemical delivery system in rabbits. J. Pharm. Sci. 1991, 80, 843-846.
    • (1991) J. Pharm. Sci. , vol.80 , pp. 843-846
    • Brewster, M.E.1    Anderson, W.2    Bodor, N.3
  • 10
    • 0025317865 scopus 로고
    • Synthesis and biological evaluation of prodrugs of Zidovudine
    • Aggarwal, S. K.; Gogu, S. R.; Rangan, S. R. S.; Agrawal, K. C. Synthesis and biological evaluation of prodrugs of Zidovudine. J. Med. Chem. 1990, 33, 1505-1510.
    • (1990) J. Med. Chem. , vol.33 , pp. 1505-1510
    • Aggarwal, S.K.1    Gogu, S.R.2    Rangan, S.R.S.3    Agrawal, K.C.4
  • 11
    • 0025350764 scopus 로고
    • Synthesis and biological properties of novel phosphotriesters: A new approach to the introduction of biologically active nucleotides into cells
    • Farrow, S. N.; Jones, A. S.; Kumar, A.; Walker, R. T.; Balzarini, J.; DeClercq, E. Synthesis and biological properties of novel phosphotriesters: a new approach to the introduction of biologically active nucleotides into cells. J. Med. Chem. 1990, 33, 1400-1406.
    • (1990) J. Med. Chem. , vol.33 , pp. 1400-1406
    • Farrow, S.N.1    Jones, A.S.2    Kumar, A.3    Walker, R.T.4    Balzarini, J.5    DeClercq, E.6
  • 12
    • 0025117883 scopus 로고
    • Cyclization-activated prodrugs. Basic esters of 5-bromo-2′-deoxyuridine
    • Saari, W.; Schwering, J. E.; Lyle, P. A.; Smith, S. J.; Engelhardt, E. L. Cyclization-activated prodrugs. Basic esters of 5-bromo-2′-deoxyuridine. J. Med. Chem. 1990, 33, 2590-2595.
    • (1990) J. Med. Chem. , vol.33 , pp. 2590-2595
    • Saari, W.1    Schwering, J.E.2    Lyle, P.A.3    Smith, S.J.4    Engelhardt, E.L.5
  • 13
    • 0027433373 scopus 로고
    • Intracellular delivery of nucleoside moniphosphates through a reductase-mediated activation process
    • Puech, F.; Gosselin, G.; Lefebvre, I.; Pompou, A.; Aubertin, A.-M.; Kirn, A.; Imbach, J.-L. Intracellular delivery of nucleoside moniphosphates through a reductase-mediated activation process. Antiviral Res. 1993, 22, 155-174.
    • (1993) Antiviral Res. , vol.22 , pp. 155-174
    • Puech, F.1    Gosselin, G.2    Lefebvre, I.3    Pompou, A.4    Aubertin, A.-M.5    Kirn, A.6    Imbach, J.-L.7
  • 14
    • 0025814856 scopus 로고
    • Lipophilic glycosyl phosphotriester derivatives of AZT: Synthesis, NMR transmembrane transport study and antiviral activity
    • Henin, Y.; Gouyette, C.; Schwartz, O.; Debouzy, J.-C.; Neumann, J.-M.; Huynh-Dinh, T. Lipophilic glycosyl phosphotriester derivatives of AZT: synthesis, NMR transmembrane transport study and antiviral activity. J. Med. Chem. 1991, 34, 1830-1837.
    • (1991) J. Med. Chem. , vol.34 , pp. 1830-1837
    • Henin, Y.1    Gouyette, C.2    Schwartz, O.3    Debouzy, J.-C.4    Neumann, J.-M.5    Huynh-Dinh, T.6
  • 16
    • 0024853372 scopus 로고
    • Synthesis and evaluation of some novel phosphate and phosphinate derivatives of araA. Studies on the mechanism of action of phosphate triesters
    • McGuigan, C.; Shackleton, J. M.; Tollerfield, S. M.; Riley, P. A. Synthesis and evaluation of some novel phosphate and phosphinate derivatives of araA. Studies on the mechanism of action of phosphate triesters. Nucleic Acids Res. 1989, 17, 10171-10177.
    • (1989) Nucleic Acids Res. , vol.17 , pp. 10171-10177
    • McGuigan, C.1    Shackleton, J.M.2    Tollerfield, S.M.3    Riley, P.A.4
  • 18
    • 0000136161 scopus 로고
    • The mechanism of hydrolysis of salicyl phosphate. I
    • Chanley, J. D.; Gindler, E. M.; Sobotka, H. The mechanism of hydrolysis of salicyl phosphate. I. J. Am. Chem. Soc. 1952, 74, 4347-4352.
    • (1952) J. Am. Chem. Soc. , vol.74 , pp. 4347-4352
    • Chanley, J.D.1    Gindler, E.M.2    Sobotka, H.3
  • 19
    • 37049115295 scopus 로고
    • Intramolecular catalysis of phosphate triester hydrolysis. Nucleophilic catalysis by the neighboring carboxyl group of the hydrolysis of dialkyl 2-carboxyphenyl phosphates
    • Bromilow, R. H.; Khan, S. A.; Kirby, A. J. Intramolecular catalysis of phosphate triester hydrolysis. Nucleophilic catalysis by the neighboring carboxyl group of the hydrolysis of dialkyl 2-carboxyphenyl phosphates. J. Chem. Soc. (B) 1971, 1091-1097.
    • (1971) J. Chem. Soc. (B) , pp. 1091-1097
    • Bromilow, R.H.1    Khan, S.A.2    Kirby, A.J.3
  • 20
    • 37049131925 scopus 로고
    • Intramolecular catalysis of phosphate diester hydrolysis. Nucleophilic catalysis by the neighboring carboxy-group of the hydrolysis of aryl 2-carboxyphenyl phosphates
    • Khan, S. A.; Kirby, A. J.; Wakselman, M.; Horning, D. P.; Lawlor, J. M. Intramolecular catalysis of phosphate diester hydrolysis. Nucleophilic catalysis by the neighboring carboxy-group of the hydrolysis of aryl 2-carboxyphenyl phosphates. J. Chem. Soc. (B) 1970, 1182-1187.
    • (1970) J. Chem. Soc. (B) , pp. 1182-1187
    • Khan, S.A.1    Kirby, A.J.2    Wakselman, M.3    Horning, D.P.4    Lawlor, J.M.5
  • 21
    • 37049106781 scopus 로고
    • Intramolecular general acid catalysis of intramolecular nucleophilic catalysis of the hydrolysis of a phosphate diester
    • Abell, K. W. Y.; Kirby, A. J. Intramolecular general acid catalysis of intramolecular nucleophilic catalysis of the hydrolysis of a phosphate diester. J. Chem. Soc., Perkin Trans. II 1983, 1171-1174.
    • (1983) J. Chem. Soc., Perkin Trans. II , pp. 1171-1174
    • Abell, K.W.Y.1    Kirby, A.J.2
  • 22
    • 0022426378 scopus 로고
    • Synthesis of Methyl O-(3-Deoxy-3-Fluoro-β-D-Galactopyranosyl)-(1-6)-β-D-Galactopyranoside and Methyl-O-(3-Deoxy-3-Fluoro-β-D-Galactopyranosyl)-(1-6)-O-β-D- Galactopyranosyl-(1-6)-β-D-Galactopyranoside
    • Kovac, P.; Yeh, H. J.; Glaudemans, C. P. J. Synthesis of Methyl O-(3-Deoxy-3-Fluoro-β-D-Galactopyranosyl)-(1-6)-β-D-Galactopyranoside and Methyl-O-(3-Deoxy-3-Fluoro-β-D-Galactopyranosyl)-(1-6)-O-β-D- Galactopyranosyl-(1-6)-β-D-Galactopyranoside. Carbohydr. Res. 1985, 140, 277-288.
    • (1985) Carbohydr. Res. , vol.140 , pp. 277-288
    • Kovac, P.1    Yeh, H.J.2    Glaudemans, C.P.J.3
  • 23
    • 0013916644 scopus 로고
    • Synthesis of Antibiotics. I. Synthesis of N-Substituted Compounds of Monochloroacrylamide and Their Antitrichophyton Effect
    • Ito, I. Synthesis of Antibiotics. I. Synthesis of N-Substituted Compounds of Monochloroacrylamide and Their Antitrichophyton Effect. Chem. Pharm. Bull. 1966, 14, 561-566.
    • (1966) Chem. Pharm. Bull. , vol.14 , pp. 561-566
    • Ito, I.1


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