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Volumn 43, Issue 11, 2000, Pages 2258-2265

Synthesis and evaluation of nitroheterocyclic phosphoramidates as hypoxia-selective alkylating agents

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; NITRO DERIVATIVE; PHOSPHORAMIDE MUSTARD; PHOSPHORAMIDIC ACID DERIVATIVE;

EID: 0034212605     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0001020     Document Type: Article
Times cited : (56)

References (25)
  • 1
    • 0023910405 scopus 로고
    • Hypoxia in tumors: A paradigm for the approach to biochemical and physiologic heterogeneity
    • (a) Coleman, C. N. Hypoxia in tumors: A paradigm for the approach to biochemical and physiologic heterogeneity. J. Natl. Cancer Inst. 1988, 80, 310-317.
    • (1988) J. Natl. Cancer Inst. , vol.80 , pp. 310-317
    • Coleman, C.N.1
  • 2
    • 0024408986 scopus 로고
    • Blood flow, oxygen and nutrient supply, and metabolic microenvironment of human tumors: A review
    • (b) Vaupel, P.; Kallinowski, F.; Okunieff, P. Blood flow, oxygen and nutrient supply, and metabolic microenvironment of human tumors: a review. Cancer Res. 1989, 49, 6449-6465.
    • (1989) Cancer Res. , vol.49 , pp. 6449-6465
    • Vaupel, P.1    Kallinowski, F.2    Okunieff, P.3
  • 3
    • 0023082510 scopus 로고
    • Tumor hypoxia: Its impact on cancer therapy
    • (c) Moulder, J. E.; Rockwell, S. Tumor hypoxia: Its impact on cancer therapy. Cancer Metastasis Rev. 1982, 5, 313-341.
    • (1982) Cancer Metastasis Rev. , vol.5 , pp. 313-341
    • Moulder, J.E.1    Rockwell, S.2
  • 4
    • 0026698228 scopus 로고
    • Use of hypoxia-directed drugs in the therapy of solid tumors
    • (a) Rockwell, S. Use of hypoxia-directed drugs in the therapy of solid tumors. Semin. Oncol. 1992, 19, 29-40.
    • (1992) Semin. Oncol. , vol.19 , pp. 29-40
    • Rockwell, S.1
  • 5
    • 0029884764 scopus 로고    scopus 로고
    • Recent developments in the design of bioreductive drugs
    • (b) Denny, W. A.; Wilson, W. R.; Hay, M. P. Recent developments in the design of bioreductive drugs. Br. J. Cancer - Suppl. 1996, 27, S32-S38.
    • (1996) Br. J. Cancer - Suppl. , vol.27
    • Denny, W.A.1    Wilson, W.R.2    Hay, M.P.3
  • 8
    • 0030900482 scopus 로고    scopus 로고
    • Hypoxia-selective antitumor agents. 15. Modification of rate of nitroreduction and extent of lysosomal uptake by polysubstitution of 4-(alkylamino)-5-nitroquinoline bioreductive drugs
    • and previous papers in the series
    • (e) Siim, B. G.; Atwell, G. J.; Anderson, R. F.; Wardman, P.; Pullen, S. M.; Wilson, W. R.; Denny, W. A. Hypoxia-selective antitumor agents. 15. Modification of rate of nitroreduction and extent of lysosomal uptake by polysubstitution of 4-(alkylamino)-5-nitroquinoline bioreductive drugs. J. Med. Chem. 1997, 40, 1381-1390 and previous papers in the series.
    • (1997) J. Med. Chem. , vol.40 , pp. 1381-1390
    • Siim, B.G.1    Atwell, G.J.2    Anderson, R.F.3    Wardman, P.4    Pullen, S.M.5    Wilson, W.R.6    Denny, W.A.7
  • 9
    • 0031706557 scopus 로고    scopus 로고
    • Radiation-activated prodrugs as hypoxia-selective cytotoxins: Model studies with nitroarylmethyl quaternary salts
    • (a) Wilson, W. R.; Tercel, M.; Anderson, R. F.; Denny, W. A. Radiation-activated prodrugs as hypoxia-selective cytotoxins: model studies with nitroarylmethyl quaternary salts. Anti-Cancer Drug Des. 1998, 13, 663-685.
    • (1998) Anti-Cancer Drug Des. , vol.13 , pp. 663-685
    • Wilson, W.R.1    Tercel, M.2    Anderson, R.F.3    Denny, W.A.4
  • 11
    • 0022535929 scopus 로고
    • Considerations for the design of nitrophenyl mustards as agents with selective toxicity for hypoxic tumor cells
    • (c) Denny, W. A.; Wilson, W. R. Considerations for the design of nitrophenyl mustards as agents with selective toxicity for hypoxic tumor cells. J. Med. Chem. 1986, 29, 879-887.
    • (1986) J. Med. Chem. , vol.29 , pp. 879-887
    • Denny, W.A.1    Wilson, W.R.2
  • 12
    • 0027219332 scopus 로고
    • Bioreducible mustards: A paradigm for hypoxia-selective prodrugs of diffusible cytotoxins (HPDCs)
    • (a) Denny, W. A. Wilson, W. R. Bioreducible mustards: A paradigm for hypoxia-selective prodrugs of diffusible cytotoxins (HPDCs). Cancer Metastasis Rev. 1993, 12, 135-151.
    • (1993) Cancer Metastasis Rev. , vol.12 , pp. 135-151
    • Denny, W.A.1    Wilson, W.R.2
  • 13
    • 0032493486 scopus 로고    scopus 로고
    • Synthesis and hypoxia-selective cytotoxicity of a 2-nitroimidazole mustard
    • (b) Lee, H. H.; Palmer B. D.; Wilson, W. R.; Denny, W. A. Synthesis and hypoxia-selective cytotoxicity of a 2-nitroimidazole mustard. Bioorg. Med. Chem. Lett. 1998, 8, 1741-1744.
    • (1998) Bioorg. Med. Chem. Lett. , vol.8 , pp. 1741-1744
    • Lee, H.H.1    Palmer, B.D.2    Wilson, W.R.3    Denny, W.A.4
  • 14
    • 0030004578 scopus 로고    scopus 로고
    • Hypoxia-selective antitumor agents. 12. Nitrobenzyl quaternary salts as bioreductive prodrugs of the alkylating agent mechlorethamine
    • (c) Tercel, M.; Wilson, W. R.; Anderson, R. F.; Denny, W. A. Hypoxia-selective antitumor agents. 12. Nitrobenzyl quaternary salts as bioreductive prodrugs of the alkylating agent mechlorethamine. J. Med. Chem. 1996, 39, 1084-1094.
    • (1996) J. Med. Chem. , vol.39 , pp. 1084-1094
    • Tercel, M.1    Wilson, W.R.2    Anderson, R.F.3    Denny, W.A.4
  • 15
    • 0025930682 scopus 로고
    • Synthesis, activation, and cytotoxicity of aldophosphamide analogues
    • (a) Borch, R. F.; Valente, R. R. Synthesis, activation, and cytotoxicity of aldophosphamide analogues. J. Med. Chem. 1991, 34, 3052-3058.
    • (1991) J. Med. Chem. , vol.34 , pp. 3052-3058
    • Borch, R.F.1    Valente, R.R.2
  • 16
    • 0025951037 scopus 로고
    • Nitroheterocycle reduction as a paradigm for intramolecular catalysis of drug delivery to hypoxic cells
    • (b) Firestone, A.; Mulcahy. R. T.; Borch, R. F. Nitroheterocycle reduction as a paradigm for intramolecular catalysis of drug delivery to hypoxic cells. J. Med. Chem. 1991, 34, 2933-2935.
    • (1991) J. Med. Chem. , vol.34 , pp. 2933-2935
    • Firestone, A.1    Mulcahy, R.T.2    Borch, R.F.3
  • 17
    • 0028276290 scopus 로고
    • Nitrobenzyl phosphorodiamidates as potential hypoxia-selective alkylating agents
    • (c) Mulcahy, R. T.; Gipp, J. J.; Schmidt, J. P.; Joswig, C.; Borch, R. F. Nitrobenzyl phosphorodiamidates as potential hypoxia-selective alkylating agents. J. Med. Chem. 1994, 37, 1610-1615.
    • (1994) J. Med. Chem. , vol.37 , pp. 1610-1615
    • Mulcahy, R.T.1    Gipp, J.J.2    Schmidt, J.P.3    Joswig, C.4    Borch, R.F.5
  • 19
  • 21
    • 0008128909 scopus 로고
    • Radical bromination of methyl 2,5-dimethyl-3-thiophenecarboxylate
    • Janda, M.; Valenta, M.; Holy, P. Radical bromination of methyl 2,5-dimethyl-3-thiophenecarboxylate. Collect. Czech. Chem. Commun. 1974, 39, 959-962.
    • (1974) Collect. Czech. Chem. Commun. , vol.39 , pp. 959-962
    • Janda, M.1    Valenta, M.2    Holy, P.3
  • 22
    • 0342759523 scopus 로고
    • Sintesie attività antibiotica di nitroderivati del tiofene. Nitroderivati di 2-tiofenchetoni, 2-tienilalchil-carbinoli, 1-(2′-tienil)-alchilamine, di 2-tenoilamidi, della tiofenina e del 2-jodotiofene
    • Bellenghi, M.; Carrara, G.; Fava, F.; Ginoulhiac, E.; Martinuzzi, C.; Vecchi, A.; Weitnauer, G. Sintesie attività antibiotica di nitroderivati del tiofene. Nitroderivati di 2-tiofenchetoni, 2-tienilalchil-carbinoli, 1-(2′-tienil)-alchilamine, di 2-tenoilamidi, della tiofenina e del 2-jodotiofene. Gazz. Chim. Ital. 1952, 82, 773-801.
    • (1952) Gazz. Chim. Ital. , vol.82 , pp. 773-801
    • Bellenghi, M.1    Carrara, G.2    Fava, F.3    Ginoulhiac, E.4    Martinuzzi, C.5    Vecchi, A.6    Weitnauer, G.7
  • 23
    • 0042620154 scopus 로고
    • 13C NMR Spectra of 1-methyl-nitropyrrole-2-aldehydes and related compounds
    • 13C NMR Spectra of 1-methyl-nitropyrrole-2-aldehydes and related compounds. Chem. Scrip. 1980, 16, 72-76.
    • (1980) Chem. Scrip. , vol.16 , pp. 72-76
    • Grehn, L.1
  • 24
    • 0016708147 scopus 로고
    • Darstellung von 5-nitroimidazolen mit heterocyclen in 2-position
    • Rufer, C.; Schwarz, K.; Winterfeldt, E. Darstellung von 5-nitroimidazolen mit heterocyclen in 2-position. Liebigs Ann. Chem. 1975, 1465-1477.
    • (1975) Liebigs Ann. Chem. , pp. 1465-1477
    • Rufer, C.1    Schwarz, K.2    Winterfeldt, E.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.