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Volumn 39, Issue 13, 1996, Pages 2518-2528

Hypoxia-selective antitumor agents. 14. Synthesis and hypoxic cell cytotoxicity of regioisomers of the hypoxia-selective cytotoxin 5-[N,N-Bis(2-chloroethyl)amino]-2,4-dinitrobenzamide

Author keywords

[No Author keywords available]

Indexed keywords

5 [N,N BIS(2 CHLOROETHYL)AMINO] 2,4 DINITROBENZAMIDE; BENZAMIDE DERIVATIVE; CYTOTOXIN; UNCLASSIFIED DRUG;

EID: 0029896076     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960057p     Document Type: Article
Times cited : (40)

References (29)
  • 1
    • 0010313514 scopus 로고
    • Tumour hypoxia: Challenges for cancer chemotherapy
    • Waring, M. J., Ponder, B. A. J., Eds.; Kluwer Academic Publishers: Lancaster
    • Wilson, W. R. Tumour hypoxia: challenges for cancer chemotherapy. In Cancer Biology and Medicine (Vol 3); Waring, M. J., Ponder, B. A. J., Eds.; Kluwer Academic Publishers: Lancaster, 1992; pp 87-131.
    • (1992) Cancer Biology and Medicine , vol.3 , pp. 87-131
    • Wilson, W.R.1
  • 2
    • 5244307080 scopus 로고    scopus 로고
    • Recent developments in the design of bioreductive drugs
    • in press
    • Denny, W. A.; Hay, M. P.; Wilson, W. R. Recent developments in the design of bioreductive drugs. Br. J. Cancer, in press.
    • Br. J. Cancer
    • Denny, W.A.1    Hay, M.P.2    Wilson, W.R.3
  • 3
    • 0028339820 scopus 로고
    • Bioreductive drugs in cancer therapy: The search for tumor specificity
    • Adams, G. E.; Stratford, I. J. Bioreductive drugs in cancer therapy: The search for tumor specificity. Int. J. Radiat. Oncol. Biol. Phys. 1994, 29, 231-238.
    • (1994) Int. J. Radiat. Oncol. Biol. Phys. , vol.29 , pp. 231-238
    • Adams, G.E.1    Stratford, I.J.2
  • 4
    • 85113073397 scopus 로고    scopus 로고
    • Hypoxia specific cytotoxins in cancer therapy
    • in press
    • Brown, J. M.; Siim, B. G. Hypoxia specific cytotoxins in cancer therapy. Semin. Radiat. Oncol., in press.
    • Semin. Radiat. Oncol.
    • Brown, J.M.1    Siim, B.G.2
  • 5
    • 0027219332 scopus 로고
    • Bioreducible mustards : A paradigm for hypoxia-selective prodrugs of diffusible cytotoxins (HPDCs)
    • Denny, W. A.; Wilson, W. R. Bioreducible mustards : a paradigm for hypoxia-selective prodrugs of diffusible cytotoxins (HPDCs). Cancer Met. Rev. 1993, 12, 135-151.
    • (1993) Cancer Met. Rev. , vol.12 , pp. 135-151
    • Denny, W.A.1    Wilson, W.R.2
  • 6
    • 0022535929 scopus 로고
    • Considerations for the design of nitrophenyl mustards as agents with selective toxicity for hypoxic mammalian cells
    • Denny, W. A.; Wilson, W. R. Considerations for the design of nitrophenyl mustards as agents with selective toxicity for hypoxic mammalian 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
  • 7
    • 0026665360 scopus 로고
    • Hypoxia-selective antitumor agents. 5. Synthesis of water-soluble nitroaniline mustards with selective cytotoxicity for hypoxic mammalian cells
    • Palmer, B. D.; Wilson, W. R.; Cliffe, S.; Denny, W. A. Hypoxia-selective antitumor agents. 5. Synthesis of water-soluble nitroaniline mustards with selective cytotoxicity for hypoxic mammalian cells. J. Med. Chem. 1992, 35, 3214-3222.
    • (1992) J. Med. Chem. , vol.35 , pp. 3214-3222
    • Palmer, B.D.1    Wilson, W.R.2    Cliffe, S.3    Denny, W.A.4
  • 8
    • 0017925519 scopus 로고
    • Structure-activity relationships in antitumor aniline mustards
    • Panthananickal, A.; Hansch, C.; Leo, A. Structure-activity relationships in antitumor aniline mustards. J. Med. Chem. 1978, 21, 16-26.
    • (1978) J. Med. Chem. , vol.21 , pp. 16-26
    • Panthananickal, A.1    Hansch, C.2    Leo, A.3
  • 9
    • 0025021102 scopus 로고
    • Hypoxia-selective antitumor agents. 3. Relationships between structure and cytotoxicity against cultured tumour cells for substituted N,N-bis(2-chloroethyl) anilines
    • Palmer, B. D.; Wilson, W. R.; Pullen, S. M.; Denny, W. A. Hypoxia-selective antitumor agents. 3. Relationships between structure and cytotoxicity against cultured tumour cells for substituted N,N-bis(2-chloroethyl) anilines. J. Med. Chem. 1990, 33, 112-121.
    • (1990) J. Med. Chem. , vol.33 , pp. 112-121
    • Palmer, B.D.1    Wilson, W.R.2    Pullen, S.M.3    Denny, W.A.4
  • 10
    • 0028916689 scopus 로고
    • Reductive chemistry of the novel hypoxia-selective cytotoxin 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzamide (SN 23862)
    • Palmer, B. D.; Van Zijl, P.; Denny, W. A.; Wilson, W. R. Reductive chemistry of the novel hypoxia-selective cytotoxin 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzamide (SN 23862). J. Med. Chem. 1995, 38, 1229-1241.
    • (1995) J. Med. Chem. , vol.38 , pp. 1229-1241
    • Palmer, B.D.1    Van Zijl, P.2    Denny, W.A.3    Wilson, W.R.4
  • 11
    • 0022978891 scopus 로고
    • CB1954 (2,4-dinitro-5-aziridinylbenzamide) becomes a DNA interstrand crosslinker in Walker tumour cells
    • Roberts, J. J.; Friedlos, F.; Knox, R. J. CB1954 (2,4-dinitro-5-aziridinylbenzamide) becomes a DNA interstrand crosslinker in Walker tumour cells. Biochem. Biophys. Res. Commun. 1986, 140, 1073-1078.
    • (1986) Biochem. Biophys. Res. Commun. , vol.140 , pp. 1073-1078
    • Roberts, J.J.1    Friedlos, F.2    Knox, R.J.3
  • 12
    • 0028246907 scopus 로고
    • Hypoxia-selective antitumor agents. 9. Structure-activity relationships for hypoxia-selective cytotoxicity among analogues of 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzamide
    • Palmer, B. D.; Wilson, W. R.; Atwell, G. J.; Schultz, D.; Xu, X. Z.; Denny, W. A. Hypoxia-selective antitumor agents. 9. Structure-activity relationships for hypoxia-selective cytotoxicity among analogues of 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzamide. J. Med. Chem. 1994, 37, 2175-2184.
    • (1994) J. Med. Chem. , vol.37 , pp. 2175-2184
    • Palmer, B.D.1    Wilson, W.R.2    Atwell, G.J.3    Schultz, D.4    Xu, X.Z.5    Denny, W.A.6
  • 13
    • 0028090161 scopus 로고
    • Self-immolative prodrugs: Candidates for antibody-directed enzyme prodrug therapy in conjunction with a nitroreductase enzyme
    • Mauger, A. B.; Burke, P. J.; Somani, H. H.; Friedlos, F.; Knox, R. J. Self-immolative prodrugs: candidates for antibody-directed enzyme prodrug therapy in conjunction with a nitroreductase enzyme. J. Med. Chem. 1994, 37, 3452-3458.
    • (1994) J. Med. Chem. , vol.37 , pp. 3452-3458
    • Mauger, A.B.1    Burke, P.J.2    Somani, H.H.3    Friedlos, F.4    Knox, R.J.5
  • 14
    • 0024205344 scopus 로고
    • The nitroreductase enzyme in Walker cells that activates 5-(aziridin-1-yl)-2,4-dinitrobenzamide (CB 1954) to 5-(aziridin-1-yl)-4-hydroxylamino-2-nitrobenzamide is a form of NAD(P)H dehydrogenase (quinone) (EC 1.6.99.2)
    • Knox, R. J.; Boland, M. P.; Friedlos, F.; Coles, B.; Southan, C.; Roberts, J. J. The nitroreductase enzyme in Walker cells that activates 5-(aziridin-1-yl)-2,4-dinitrobenzamide (CB 1954) to 5-(aziridin-1-yl)-4-hydroxylamino-2-nitrobenzamide is a form of NAD(P)H dehydrogenase (quinone) (EC 1.6.99.2). Biochem. Pharmacol. 1988, 37, 4671-4677.
    • (1988) Biochem. Pharmacol. , vol.37 , pp. 4671-4677
    • Knox, R.J.1    Boland, M.P.2    Friedlos, F.3    Coles, B.4    Southan, C.5    Roberts, J.J.6
  • 16
    • 84981838165 scopus 로고
    • On 4,6-dinitro-3-chlorobenzoic acid
    • Goldstein, H.; Stamm, R. On 4,6-dinitro-3-chlorobenzoic acid. Helv. Chim. Acta 1952, 35, 1330-1332.
    • (1952) Helv. Chim. Acta , vol.35 , pp. 1330-1332
    • Goldstein, H.1    Stamm, R.2
  • 17
    • 5244251546 scopus 로고    scopus 로고
    • note
    • We note that under IUPAC rules 20 is named 3-chloro-4,6-dinitrobenzoic acid rather than 5-chloro-2,4-dinitrobenzoic acid. However, to be consistent with our previous publications and previous literature on the related compound CB 1954 (1), we have chosen to use the former numbering for 20 and its analogues in this paper.
  • 18
    • 37049142540 scopus 로고
    • Semiquinone free radicals and oxygen. Pulse radiolysis study of one-electron transfer equilibria
    • Patel, K. B.; Willson, R. L. Semiquinone free radicals and oxygen. Pulse radiolysis study of one-electron transfer equilibria. J. Chem. Soc., Faraday Trans. 1973, 69, 814-819.
    • (1973) J. Chem. Soc., Faraday Trans. , vol.69 , pp. 814-819
    • Patel, K.B.1    Willson, R.L.2
  • 19
    • 0024529829 scopus 로고
    • Hypoxia-selective antitumor agents. 2. Electronic effects of 4-substituents on the mechanisms of cytotoxicity and metabolic stability of nitracrine analogues
    • Wilson, W. R.; Thompson, L. H.; Anderson, R. F.; Denny, W. A. Hypoxia-selective antitumor agents. 2. Electronic effects of 4-substituents on the mechanisms of cytotoxicity and metabolic stability of nitracrine analogues. J. Med. Chem. 1989, 32, 31-38.
    • (1989) J. Med. Chem. , vol.32 , pp. 31-38
    • Wilson, W.R.1    Thompson, L.H.2    Anderson, R.F.3    Denny, W.A.4
  • 20
    • 0021824209 scopus 로고
    • Defective DNA cross-link removal in Chinese hamster cell mutants hypersensitive to bifunctional alkylating agents
    • Hoy, C. A.; Thompson, L. H.; Mooney, C. L.; Salazar, E. P. Defective DNA cross-link removal in Chinese hamster cell mutants hypersensitive to bifunctional alkylating agents. Cancer Res. 1985, 45, 1737-1743.
    • (1985) Cancer Res. , vol.45 , pp. 1737-1743
    • Hoy, C.A.1    Thompson, L.H.2    Mooney, C.L.3    Salazar, E.P.4
  • 21
    • 0024491246 scopus 로고
    • Hypoxia-selective antitumor agents. 1. Relationships between structure, redox properties and hypoxia-selective cytotoxicity for 4-substituted derivatives of nitracrine
    • Wilson, W. R.; Anderson, R. F.; Denny, W. A. Hypoxia-selective antitumor agents. 1. Relationships between structure, redox properties and hypoxia-selective cytotoxicity for 4-substituted derivatives of nitracrine. J. Med. Chem. 1989, 32, 23-30.
    • (1989) J. Med. Chem. , vol.32 , pp. 23-30
    • Wilson, W.R.1    Anderson, R.F.2    Denny, W.A.3
  • 23
    • 0028952450 scopus 로고
    • N-[2-(2-Methyl-5-nitroimidazol-1H-yl)ethyl]-4-(2-nitroimidazol-1H-yl)- butanamide (SN 24699), a bis-nitroimidazole with enhanced selectivity for hypoxic cells in vitro
    • Moselen, J. W.; Hay, M. P.; Denny, W. A.; Wilson, W. R. N-[2-(2-Methyl-5-nitroimidazol-1H-yl)ethyl]-4-(2-nitroimidazol-1H-yl)-butanamide (SN 24699), a bis-nitroimidazole with enhanced selectivity for hypoxic cells in vitro. Cancer Res. 1995, 55, 574-580.
    • (1995) Cancer Res. , vol.55 , pp. 574-580
    • Moselen, J.W.1    Hay, M.P.2    Denny, W.A.3    Wilson, W.R.4
  • 24
    • 84981834315 scopus 로고
    • Nitration of 2-nitro-4-chlorobenzoic acid
    • Goldstein, H.; Schaaf, E. Nitration of 2-nitro-4-chlorobenzoic acid. Helv. Chim. Acta 1957, 40, 369-376.
    • (1957) Helv. Chim. Acta , vol.40 , pp. 369-376
    • Goldstein, H.1    Schaaf, E.2
  • 25
    • 0011861272 scopus 로고
    • Relation of chemical structure to antibacterial activity among analogs of dimethyldiaminobenzene
    • Woolley, D. W.; Pringle, A.; Smith, N.; Singer, E. A.; Schnaffner, G. Relation of chemical structure to antibacterial activity among analogs of dimethyldiaminobenzene. J. Biol. Chem. 1952, 194, 729-746.
    • (1952) J. Biol. Chem. , vol.194 , pp. 729-746
    • Woolley, D.W.1    Pringle, A.2    Smith, N.3    Singer, E.A.4    Schnaffner, G.5
  • 27
    • 0021166371 scopus 로고
    • A semiautomated microculture method for investigating growth inhibitory effects of cytotoxic compounds on exponentially growing carcinoma cells
    • Finlay, G. J.; Baguley, B. C.; Wilson, W. R. A semiautomated microculture method for investigating growth inhibitory effects of cytotoxic compounds on exponentially growing carcinoma cells. Anal. Biochem. 1984, 139, 272-277.
    • (1984) Anal. Biochem. , vol.139 , pp. 272-277
    • Finlay, G.J.1    Baguley, B.C.2    Wilson, W.R.3
  • 28
    • 0028261377 scopus 로고
    • Hypoxia-selective antitumor agents. 8. Bis(nitroimidazolyl)alkanecarboxamides: A new class of hypoxia-selective cytotoxins and hypoxic cell radiosensitizers
    • Hay, M. P.; Wilson, W. R.; Moselen, J. W.; Palmer, B. D.; Denny, W. A. Hypoxia-selective antitumor agents. 8. Bis(nitroimidazolyl)alkanecarboxamides: A new class of hypoxia-selective cytotoxins and hypoxic cell radiosensitizers. J. Med. Chem. 1994, 37, 381-391.
    • (1994) J. Med. Chem. , vol.37 , pp. 381-391
    • Hay, M.P.1    Wilson, W.R.2    Moselen, J.W.3    Palmer, B.D.4    Denny, W.A.5
  • 29
    • 0016257209 scopus 로고
    • An in vitro assay to measure the viability of KHT tumor cells not previously exposed to culture conditions
    • Thomson, J. E.; Rauth, A. M. An in vitro assay to measure the viability of KHT tumor cells not previously exposed to culture conditions. Radiat. Res. 1974, 58, 262-276.
    • (1974) Radiat. Res. , vol.58 , pp. 262-276
    • Thomson, J.E.1    Rauth, A.M.2


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