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Volumn 7, Issue 7, 2014, Pages 797-838

The medicinal chemistry of imidazotetrazine prodrugs

Author keywords

Azolotetrazinone; DNA alkylation; DNA mismatch repair; MGMT; Mitozolomide; Temozolomide

Indexed keywords

DACARBAZINE; DNA; IMIDAZOTETRAZINE; METHYLATED DNA PROTEIN CYSTEINE METHYLTRANSFERASE; MISMATCH REPAIR PROTEIN; PRODRUG; TEMOZOLOMIDE; UNCLASSIFIED DRUG;

EID: 84904197222     PISSN: None     EISSN: 14248247     Source Type: Journal    
DOI: 10.3390/ph7070797     Document Type: Review
Times cited : (59)

References (97)
  • 1
    • 0030993717 scopus 로고    scopus 로고
    • Temozolomide: A review of its discovery, chemical properties, pre-clinical development and clinical trials
    • Newlands, E.S.; Stevens, M.F.G.; Wedge, S.R.; Wheelhouse, R.T.; Brock, C. Temozolomide: a review of its discovery, chemical properties, pre-clinical development and clinical trials. Cancer Treat. Rev. 1997, 23, 35-61.
    • (1997) Cancer Treat. Rev , vol.23 , pp. 35-61
    • Newlands, E.S.1    Stevens, M.F.G.2    Wedge, S.R.3    Wheelhouse, R.T.4    Brock, C.5
  • 2
    • 68049123621 scopus 로고    scopus 로고
    • Temozolomide: From cytotoxic to molecularly-targeted agent
    • Cancer Drug Design and Discovery; Neidle, S., Ed.; Elsevier: Amsterdam
    • Stevens, M.F.G. Temozolomide: From cytotoxic to molecularly-targeted agent. In Cancer Drug Design and Discovery; Neidle, S., Ed.; Elsevier: Amsterdam, The Netherlands, 2008; pp. 157-172.
    • (2008) , pp. 157-172
    • Stevens, M.F.G.1
  • 3
    • 0037818564 scopus 로고    scopus 로고
    • Temozolomide a review of its use in the treatment of malignant gliomas, malignant melanoma and other advanced cancers
    • Darkes, M.J.M.; Plosker, G.L.; Jarvis, B. Temozolomide a review of its use in the treatment of malignant gliomas, malignant melanoma and other advanced cancers. Am. J. Cancer 2002, 1, 55-80.
    • (2002) Am. J. Cancer , vol.1 , pp. 55-80
    • Darkes, M.J.M.1    Plosker, G.L.2    Jarvis, B.3
  • 4
    • 0033941733 scopus 로고    scopus 로고
    • Temozolomide and treatment of malignant glioma
    • Friedman, H.S.; Kerby, T.; Calvert, H. Temozolomide and treatment of malignant glioma. Clin. Cancer Res. 2000, 6, 2585-2597.
    • (2000) Clin. Cancer Res , vol.6 , pp. 2585-2597
    • Friedman, H.S.1    Kerby, T.2    Calvert, H.3
  • 5
    • 0010586158 scopus 로고
    • The Chemistry of azolotetrazinones
    • Ed.; Blackie & Son Ltd.: Bel Air, CA, USA
    • Threadgill, M.D. The Chemistry of azolotetrazinones. In The Chemistry of Antitumour Agents; Wilman, D.E.V., Ed.; Blackie & Son Ltd.: Bel Air, CA, USA, 1990; pp. 187-201.
    • (1990) The Chemistry of Antitumour Agents; Wilman, D.E.V , pp. 187-201
    • Threadgill, M.D.1
  • 8
    • 0037027991 scopus 로고    scopus 로고
    • Antitumor imidazotetrazines. 40. Radiosyntheses of [4-11C-carbonyl]- and [3-N-11C-methyl]-8- carbamoyl-3-methylimidazo[5,1-d]-1,2,3,5-tetrazin-4(3H)-one (temozolomide) for positron emission tomography (PET) Studies
    • Brown, G.D.; Luthra, S.K.; Brock, C.S.; Stevens, M.F.G.; Price, P.M.; Brady, F. Antitumor imidazotetrazines. 40. Radiosyntheses of [4-11C-carbonyl]- and [3-N-11C-methyl]-8- carbamoyl-3-methylimidazo[5,1-d]-1,2,3,5-tetrazin-4(3H)-one (temozolomide) for positron emission tomography (PET) Studies. J. Med. Chem. 2002, 45, 5448-5457.
    • (2002) J. Med. Chem , vol.45 , pp. 5448-5457
    • Brown, G.D.1    Luthra, S.K.2    Brock, C.S.3    Stevens, M.F.G.4    Price, P.M.5    Brady, F.6
  • 9
    • 0023605735 scopus 로고
    • Antitumor activity and pharmacokinetics in mice of 8-carbamoyl-3-methyl-imidazo[5,1-d]-1,2,3,5-tetrazin-4(3H)-one (CCRG 81045; M & B 39831), a novel drug with potential as an alternative to dacarbazine
    • Stevens, M.F.G.; Hickman, J.A.; Langdon, S.P.; Chubb, D.; Vickers, L.; Stone, R.; Baig, G.; Goddard, C.; Gibson, N.W.; Slack, J.A. et al. Antitumor activity and pharmacokinetics in mice of 8-carbamoyl-3-methyl-imidazo[5,1-d]-1,2,3,5-tetrazin-4(3H)-one (CCRG 81045; M & B 39831), a novel drug with potential as an alternative to dacarbazine. Cancer Res. 1987, 47, 5846-5852.
    • (1987) Cancer Res , vol.47 , pp. 5846-5852
    • Stevens, M.F.G.1    Hickman, J.A.2    Langdon, S.P.3    Chubb, D.4    Vickers, L.5    Stone, R.6    Baig, G.7    Goddard, C.8    Gibson, N.W.9    Slack, J.A.10
  • 10
    • 0026029701 scopus 로고
    • Comparison of the cytotoxicity in vitro of temozolomide and dacarbazine, prodrugs of 3-methyl-(triazen-1-yl)imidazole-4-carboxamide
    • Tsang, L.L.H.; Quarterman, C.P.; Gescher, A.; Slack, J.A. Comparison of the cytotoxicity in vitro of temozolomide and dacarbazine, prodrugs of 3-methyl-(triazen-1-yl)imidazole-4-carboxamide. Cancer Chemother. Pharmacol. 1991, 27, 342-346.
    • (1991) Cancer Chemother. Pharmacol , vol.27 , pp. 342-346
    • Tsang, L.L.H.1    Quarterman, C.P.2    Gescher, A.3    Slack, J.A.4
  • 11
    • 84862925785 scopus 로고    scopus 로고
    • Temozolomide: Mechanisms of action, repair and resistance
    • Zhang, J.; Stevens, M.F.G.; Bradshaw, T.D. Temozolomide: Mechanisms of action, repair and resistance. Curr. Mol. Pharmacol. 2012, 5, 102-114.
    • (2012) Curr. Mol. Pharmacol , vol.5 , pp. 102-114
    • Zhang, J.1    Stevens, M.F.G.2    Bradshaw, T.D.3
  • 15
    • 0027161181 scopus 로고
    • Decomposition of the antitumour drug temozolomide in deuteriated phosphate buffer: Methyl group transfer is accompanied by deuterium exchange
    • Wheelhouse, R.T.; Stevens, M.F.G. Decomposition of the antitumour drug temozolomide in deuteriated phosphate buffer: methyl group transfer is accompanied by deuterium exchange. Chem. Commun. 1993, 1177-1178.
    • (1993) Chem. Commun , pp. 1177-1178
    • Wheelhouse, R.T.1    Stevens, M.F.G.2
  • 16
    • 0028133013 scopus 로고
    • NMR and molecular modeling investigation of the mechanism of activation of the antitumor drug temozolomide and its interaction with DNA
    • Denny, B.J.; Wheelhouse, R.T.; Stevens, M.F.G.; Tsang, L.L.; Slack, J.A. NMR and molecular modeling investigation of the mechanism of activation of the antitumor drug temozolomide and its interaction with DNA. Biochemistry 1994, 33, 9045-9051.
    • (1994) Biochemistry , vol.33 , pp. 9045-9051
    • Denny, B.J.1    Wheelhouse, R.T.2    Stevens, M.F.G.3    Tsang, L.L.4    Slack, J.A.5
  • 18
    • 84904171096 scopus 로고
    • Diazomethane-d2 (CD2N2)
    • Campbell, J.R. Diazomethane-d2 (CD2N2). Chem. Ind. 1972, 540.
    • (1972) Chem. Ind , pp. 540
    • Campbell, J.R.1
  • 19
    • 0023123974 scopus 로고
    • Antitumor imidazotetrazines. 14. Synthesis and antitumor activity of 6- and 8-substituted imidazo[5,1-d]-1,2,3,5-tetrazinones and 8-substituted pyrazolo[5,1-d]-1,2,3,5-tetrazinones
    • Lunt, E.; Newton, C.G.; Smith, C.; Stevens, G.P.; Stevens, M.F.G.; Straw, C.G.; Walsh, R.J.A.; Warren, P.J.; Fizames, C.; Lavelle, F. et al. Antitumor imidazotetrazines. 14. Synthesis and antitumor activity of 6- and 8-substituted imidazo[5,1-d]-1,2,3,5-tetrazinones and 8-substituted pyrazolo[5,1-d]-1,2,3,5-tetrazinones. J. Med. Chem. 1987, 30, 357-366.
    • (1987) J. Med. Chem , vol.30 , pp. 357-366
    • Lunt, E.1    Newton, C.G.2    Smith, C.3    Stevens, G.P.4    Stevens, M.F.G.5    Straw, C.G.6    Walsh, R.J.A.7    Warren, P.J.8    Fizames, C.9    Lavelle, F.10
  • 20
    • 0021289188 scopus 로고
    • Antitumor imidazotetrazines. 1. Synthesis and chemistry of 8-carbamoyl-3-(2- chloroethyl)imidazo[5,1-d]-1,2,3,5-tetrazin-4(3H)-one, a novel broad-spectrum antitumor agent
    • Stevens, M.F.G.; Hickman, J.A.; Stone, R.; Gibson, N.W.; Baig, G.U.; Lunt, E.; Newton, C.G. Antitumor imidazotetrazines. 1. Synthesis and chemistry of 8-carbamoyl-3-(2- chloroethyl)imidazo[5,1-d]-1,2,3,5-tetrazin-4(3H)-one, a novel broad-spectrum antitumor agent. J. Med. Chem. 1984, 27, 196-201.
    • (1984) J. Med. Chem , vol.27 , pp. 196-201
    • Stevens, M.F.G.1    Hickman, J.A.2    Stone, R.3    Gibson, N.W.4    Baig, G.U.5    Lunt, E.6    Newton, C.G.7
  • 21
    • 0019868892 scopus 로고
    • Synthesis of specifically 15N- and 13C-labeled antitumor (2-haloethyl)nitrosoureas. The study of their conformations in solution by nitrogen-15 and carbon-13 nuclear magnetic resonance and evidence for stereoelectronic control in their aqueous decomposition
    • Lown, J.W.; Chauhan, S.M.S. Synthesis of specifically 15N- and 13C-labeled antitumor (2-haloethyl)nitrosoureas. The study of their conformations in solution by nitrogen-15 and carbon-13 nuclear magnetic resonance and evidence for stereoelectronic control in their aqueous decomposition. J. Org. Chem. 1981, 46, 5309-5321.
    • (1981) J. Org. Chem , vol.46 , pp. 5309-5321
    • Lown, J.W.1    Chauhan, S.M.S.2
  • 22
    • 0022640293 scopus 로고
    • DNA sequence selectivity of guanine-N7 alkylation by three antitumor chloroethylating agents
    • Hartley, J.A.; Gibson, N.W.; Kohn, K.W.; Mattes, W.B. DNA sequence selectivity of guanine-N7 alkylation by three antitumor chloroethylating agents. Cancer Res. 1986, 46, 1943-1947.
    • (1986) Cancer Res , vol.46 , pp. 1943-1947
    • Hartley, J.A.1    Gibson, N.W.2    Kohn, K.W.3    Mattes, W.B.4
  • 23
    • 0021272810 scopus 로고
    • Antitumour imidazotetrazines-IV An investigation into the mechanism of antitumour activity of a novel and potent antitumour agent, mitozolomide (CCRG 81010, M & B 39565; NSC 353451)
    • Horgan, C.M.T.; Tisdale, M.J. Antitumour imidazotetrazines-IV An investigation into the mechanism of antitumour activity of a novel and potent antitumour agent, mitozolomide (CCRG 81010, M & B 39565; NSC 353451). Biochem. Pharmacol. 1984, 33, 2185-2192.
    • (1984) Biochem. Pharmacol , vol.33 , pp. 2185-2192
    • Horgan, C.M.T.1    Tisdale, M.J.2
  • 24
    • 0028956350 scopus 로고
    • Antitumor imidazotetrazines. 32. Synthesis of novel imidazotetrazinones and related bicyclic heterocycles to probe the mode of action of the antitumor drug temozolomide
    • Clark, A.S.; Deans, B.; Stevens, M.F.G.; Tisdale, M.J.; Wheelhouse, R.T.; Denny, B.J.; Hartley, J.A. Antitumor imidazotetrazines. 32. Synthesis of novel imidazotetrazinones and related bicyclic heterocycles to probe the mode of action of the antitumor drug temozolomide. J. Med. Chem. 1995, 38, 1493-1504.
    • (1995) J. Med. Chem , vol.38 , pp. 1493-1504
    • Clark, A.S.1    Deans, B.2    Stevens, M.F.G.3    Tisdale, M.J.4    Wheelhouse, R.T.5    Denny, B.J.6    Hartley, J.A.7
  • 25
    • 33748507110 scopus 로고    scopus 로고
    • Antitumour imidazotetrazines. Part 36. Conversion of 5-amino-imidazole-4-carboxamide to imidazo [5,1-d][1,2,3,5]tetrazin-4(3H)-ones and imidazo[1,5-a][1,3,5]triazin-4(3H)-ones related in structure to the antitumour agents temozolomide and mitozolomide
    • Wang, Y.; Wheelhouse, R.T.; Zhao, L.; Langnel, D.A.F.; Stevens, M.F.G. Antitumour imidazotetrazines. Part 36. Conversion of 5-amino-imidazole-4-carboxamide to imidazo [5,1-d][1,2,3,5]tetrazin-4(3H)-ones and imidazo[1,5-a][1,3,5]triazin-4(3H)-ones related in structure to the antitumour agents temozolomide and mitozolomide. J. Chem. Soc. Perkin Trans. 1998, 1, 1669-1675.
    • (1998) J. Chem. Soc. Perkin Trans , vol.1 , pp. 1669-1675
    • Wang, Y.1    Wheelhouse, R.T.2    Zhao, L.3    Langnel, D.A.F.4    Stevens, M.F.G.5
  • 26
    • 37049075486 scopus 로고
    • Antitumour imidazotetrazines. Part 31. The synthesis of isotopically labelled temozolomide and a multinuclear (1H, 13C, 15N) magnetic resonance investigation of temozolomide and mitozolomide
    • Wheelhouse, R.T.; Wilman, D.E.V; Thomson, W.; Stevens, M.F.G. Antitumour imidazotetrazines. Part 31. The synthesis of isotopically labelled temozolomide and a multinuclear (1H, 13C, 15N) magnetic resonance investigation of temozolomide and mitozolomide. J. Chem. Soc. Perkin Trans. 1995, 1, 249-252.
    • (1995) J. Chem. Soc. Perkin Trans , vol.1 , pp. 249-252
    • Wheelhouse, R.T.1    Wilman, D.E.V.2    Thomson, W.3    Stevens, M.F.G.4
  • 28
    • 0000957074 scopus 로고
    • Hydrolysis of diazomethane-Kinetics and mechanism
    • McGarrity, J.F.; Smyth, T. Hydrolysis of diazomethane-Kinetics and mechanism. J. Am. Chem. Soc. 1980, 102, 7303-7308.
    • (1980) J. Am. Chem. Soc , vol.102 , pp. 7303-7308
    • McGarrity, J.F.1    Smyth, T.2
  • 30
    • 84863037728 scopus 로고    scopus 로고
    • The effect of temozolomide/poly (lactide-co-glycolide) (PLGA)/nano-hydroxyapatite microspheres on glioma U87 cells behavior
    • Zhang, D.; Tian, A.; Xue, X.; Wang, M.; Qiu, B.; Wu, A. The effect of temozolomide/poly (lactide-co-glycolide) (PLGA)/nano-hydroxyapatite microspheres on glioma U87 cells behavior. Int. J. Mol. Sci. 2012, 13, 1109-1125.
    • (2012) Int. J. Mol. Sci , vol.13 , pp. 1109-1125
    • Zhang, D.1    Tian, A.2    Xue, X.3    Wang, M.4    Qiu, B.5    Wu, A.6
  • 31
    • 84904208204 scopus 로고    scopus 로고
    • Crystalline temozolomide monohydrate and process for preparation thereof
    • WO2008111092A1, 18 September
    • Panda, B.; Maikap, G.C.; Agarwal, S.K.; Singh, M.K.; Jaggi, M. Crystalline temozolomide monohydrate and process for preparation thereof. Int. Pat. WO2008111092A1, 18 September 2008.
    • (2008) Int. Pat
    • Panda, B.1    Maikap, G.C.2    Agarwal, S.K.3    Singh, M.K.4    Jaggi, M.5
  • 33
    • 0026738074 scopus 로고
    • Antitumor imidazotetrazines. 25. Crystal structure of 8-carbamoyl-3-methylimidazo[5,1-d]-1,2,3,5-tetrazin- (3H)-one (temozolomide) and structural comparisons with the related drugs mitozolomide and DTIC
    • Lowe, P.R.; Sansom, C.E.; Schwalbe, C.H.; Stevens, M.F.G.; Clark, A.S. Antitumor imidazotetrazines. 25. Crystal structure of 8-carbamoyl-3-methylimidazo[5,1-d]-1,2,3,5-tetrazin- (3H)-one (temozolomide) and structural comparisons with the related drugs mitozolomide and DTIC. J. Med. Chem. 1992, 35, 3377-3382.
    • (1992) J. Med. Chem , vol.35 , pp. 3377-3382
    • Lowe, P.R.1    Sansom, C.E.2    Schwalbe, C.H.3    Stevens, M.F.G.4    Clark, A.S.5
  • 34
    • 49149103008 scopus 로고    scopus 로고
    • Polymorphs and polymorphic cocrystals of temozolomide
    • Babu, N.J.; Reddy, L.S.; Aitipamula, S.; Nangia, A. Polymorphs and polymorphic cocrystals of temozolomide. Chem. Asian J. 2008, 3, 1122-1133.
    • (2008) Chem. Asian J , vol.3 , pp. 1122-1133
    • Babu, N.J.1    Reddy, L.S.2    Aitipamula, S.3    Nangia, A.4
  • 35
    • 84866371800 scopus 로고    scopus 로고
    • Crystal engineering of stable temozolomide cocrystals
    • Babu, N.J.; Sanphui, P.; Nangia, A. Crystal engineering of stable temozolomide cocrystals. Chem. Asian J. 2012, 7, 2274-2285.
    • (2012) Chem. Asian J , vol.7 , pp. 2274-2285
    • Babu, N.J.1    Sanphui, P.2    Nangia, A.3
  • 36
    • 84877045608 scopus 로고    scopus 로고
    • Temozolomide cocrystals with carboxamide coformers
    • Sanphui, P.; Babu, N.J.; Nangia, A. Temozolomide cocrystals with carboxamide coformers. Cryst. Growth Des. 2013, 13, 2208-2219.
    • (2013) Cryst. Growth Des , vol.13 , pp. 2208-2219
    • Sanphui, P.1    Babu, N.J.2    Nangia, A.3
  • 37
    • 84866338368 scopus 로고    scopus 로고
    • Synthesis and crystal structure of a cadmium complex of temozolomide
    • Liu, Y.; Wang, H.; Wei, J.; Zhou, R.; Chen, Z.; Liang, H. Synthesis and crystal structure of a cadmium complex of temozolomide. J. Chem. Res. 2012, 36, 520-522.
    • (2012) J. Chem. Res , vol.36 , pp. 520-522
    • Liu, Y.1    Wang, H.2    Wei, J.3    Zhou, R.4    Chen, Z.5    Liang, H.6
  • 38
    • 84866245672 scopus 로고    scopus 로고
    • Enhanced stability and activity of temozolomide in primary glioblastoma multiforme cells with cucurbit[n]uril
    • Appel, E.A.; Rowland, M.J.; Loh, X.J.; Heywood, R.M.; Watts, C.; Scherman, O.A. Enhanced stability and activity of temozolomide in primary glioblastoma multiforme cells with cucurbit[n]uril. Chem. Commun. 2012, 48, 9843-9845.
    • (2012) Chem. Commun , vol.48 , pp. 9843-9845
    • Appel, E.A.1    Rowland, M.J.2    Loh, X.J.3    Heywood, R.M.4    Watts, C.5    Scherman, O.A.6
  • 39
    • 0037879646 scopus 로고
    • [7+2]- and [11+2]-Cycloaddition reactions of diazo-azoles with isocyanates to azolo[5,1-d][1,2,3,5]tetrazine-4-ones
    • Ege, G.; Gilbert, K. [7+2]- and [11+2]-Cycloaddition reactions of diazo-azoles with isocyanates to azolo[5,1-d][1,2,3,5]tetrazine-4-ones. Tetrahedron Lett. 1979, 20, 4253-4256.
    • (1979) Tetrahedron Lett , vol.20 , pp. 4253-4256
    • Ege, G.1    Gilbert, K.2
  • 40
    • 0000360901 scopus 로고
    • Synthesis of potential anticancer agents. XXIX. 5-Diazoimidazole-4-carboxamide and 5-diazo-ν-triazole-4-carboxamide
    • Shealy, Y.F.; Struck, R.F.; Holum, L.B.; Montgomery, J.A. Synthesis of potential anticancer agents. XXIX. 5-Diazoimidazole-4-carboxamide and 5-diazo-ν-triazole-4-carboxamide. J. Org. Chem. 1961, 26, 2396-2401.
    • (1961) J. Org. Chem , vol.26 , pp. 2396-2401
    • Shealy, Y.F.1    Struck, R.F.2    Holum, L.B.3    Montgomery, J.A.4
  • 41
    • 0003498455 scopus 로고
    • Some imidazo-1,2,3-triazenes and their biological relationship to the purines
    • Woolley, D.W.; Shaw, E. Some imidazo-1,2,3-triazenes and their biological relationship to the purines. J. Biol. Chem. 1951, 189, 401-410.
    • (1951) J. Biol. Chem , vol.189 , pp. 401-410
    • Woolley, D.W.1    Shaw, E.2
  • 42
    • 37049110824 scopus 로고
    • Triazenes and related products. Part 23. New photo-products from 5- diazoimidazole-4-carboxamide (diazo-IC)
    • Horton, K.; Stevens, M.F.G. Triazenes and related products. Part 23. New photo-products from 5- diazoimidazole-4-carboxamide (diazo-IC). J. Chem. Soc. Perkin Trans. 1981, 1, 1433-1436.
    • (1981) J. Chem. Soc. Perkin Trans , vol.1 , pp. 1433-1436
    • Horton, K.1    Stevens, M.F.G.2
  • 43
    • 0030048592 scopus 로고    scopus 로고
    • Synthetic studies of 8-carbamoylimidazo-[5,1-d]-1,2,3,5-tetrazin- 4(3H)-one: A key derivative of antitumour drug temozolomide
    • Wang, Y.; Stevens, M.F.G. Synthetic studies of 8-carbamoylimidazo-[5,1-d]-1,2,3,5-tetrazin- 4(3H)-one: A key derivative of antitumour drug temozolomide. Bioorganic Med. Chem. Lett. 1996, 3, 185-188.
    • (1996) Bioorganic Med. Chem. Lett , vol.3 , pp. 185-188
    • Wang, Y.1    Stevens, M.F.G.2
  • 44
    • 84904206733 scopus 로고    scopus 로고
    • University of Bradford, Bradford, UK. Unpublished data
    • Pletsas, D.; Karodia, N.; Wheelhouse, R.T. University of Bradford, Bradford, UK. Unpublished data.
    • Pletsas, D.1    Karodia, N.2    Wheelhouse, R.T.3
  • 45
    • 0037027989 scopus 로고    scopus 로고
    • Antitumor imidazotetrazines. 41. Conjugation of the antitumor agents mitozolomide and temozolomide to peptides and lexitropsins bearing DNA major and minor groove-binding structural motifs
    • Arrowsmith, J.; Jennings, S.A.; Clark, A.S.; Stevens, M.F.G. Antitumor imidazotetrazines. 41. Conjugation of the antitumor agents mitozolomide and temozolomide to peptides and lexitropsins bearing DNA major and minor groove-binding structural motifs. J. Med. Chem. 2002, 45, 5458-5470.
    • (2002) J. Med. Chem , vol.45 , pp. 5458-5470
    • Arrowsmith, J.1    Jennings, S.A.2    Clark, A.S.3    Stevens, M.F.G.4
  • 46
    • 0028216764 scopus 로고
    • Alternative syntheses of the antitumour drug temozolomide avoiding the use of methyl isocyanate
    • Wang, Y.; Stevens, M.F.G.; Thomson, W. Alternative syntheses of the antitumour drug temozolomide avoiding the use of methyl isocyanate. J. Chem. Soc. Chem. Commun. 1994, 1687-1688.
    • (1994) J. Chem. Soc. Chem. Commun , pp. 1687-1688
    • Wang, Y.1    Stevens, M.F.G.2    Thomson, W.3
  • 48
    • 37049080425 scopus 로고
    • Antitumour imidazotetrazines. Part 33. New syntheses of the antitumour drug temozolomide using "masked" methyl isocyanates
    • Wang, Y.; Stevens, M.F.G.; Thomson, W.T.; Shutts, B.P. Antitumour imidazotetrazines. Part 33. New syntheses of the antitumour drug temozolomide using "masked" methyl isocyanates. J. Chem. Soc. Perkin Trans. 1995, 1, 2783-2787.
    • (1995) J. Chem. Soc. Perkin Trans , vol.1 , pp. 2783-2787
    • Wang, Y.1    Stevens, M.F.G.2    Thomson, W.T.3    Shutts, B.P.4
  • 49
    • 0031043640 scopus 로고    scopus 로고
    • A new route to the antitumour drug temozolomide, but not thiotemozolomide
    • Wang, Y.; Lowe, P.R.; Thomson, W.T.; Clark, J.; Stevens, M.F.G. A new route to the antitumour drug temozolomide, but not thiotemozolomide. Chem. Commun. 1997, 363-364.
    • (1997) Chem. Commun , pp. 363-364
    • Wang, Y.1    Lowe, P.R.2    Thomson, W.T.3    Clark, J.4    Stevens, M.F.G.5
  • 59
    • 85083008636 scopus 로고
    • A simple and versatile synthesis of trimethylsiloxy-substituted isocyanates
    • Mormann, W.; Leukel, G. A simple and versatile synthesis of trimethylsiloxy-substituted isocyanates. Synthesis-Stuttgart 1988, 12, 990-992.
    • (1988) Synthesis-Stuttgart , vol.12 , pp. 990-992
    • Mormann, W.1    Leukel, G.2
  • 60
    • 0025096409 scopus 로고
    • Characterisation of urinary metabolites of temozolomide in humans and mice and evaluation of their cytotoxicity
    • Tsang, L.L.H.; Farmer, P.B.; Gescher, A.; Slack, J.A. Characterisation of urinary metabolites of temozolomide in humans and mice and evaluation of their cytotoxicity. Cancer Chemother. Pharmacol. 1990, 26, 429-436.
    • (1990) Cancer Chemother Pharmacol , vol.26 , pp. 429-436
    • Tsang, L.L.H.1    Farmer, P.B.2    Gescher, A.3    Slack, J.A.4
  • 62
    • 58149161532 scopus 로고    scopus 로고
    • Activation of KATP channels increases anticancer drug delivery to brain tumors and survival
    • Ningaraj, N.S.; Sankpal, U.T.; Khaitan, D.; Meister, E.A.; Vats, T. Activation of KATP channels increases anticancer drug delivery to brain tumors and survival. Eur. J. Pharmacol. 2009, 602, 188-193.
    • (2009) Eur. J. Pharmacol , vol.602 , pp. 188-193
    • Ningaraj, N.S.1    Sankpal, U.T.2    Khaitan, D.3    Meister, E.A.4    Vats, T.5
  • 63
    • 84870947124 scopus 로고    scopus 로고
    • An efficient and practical radiosynthesis of [11C]temozolomide
    • Moseley, C.K.; Carlin, S.M.; Neelamegam, R.; Hooker, J.M. An efficient and practical radiosynthesis of [11C]temozolomide. Org. Lett. 2012, 14, 5872-8575.
    • (2012) Org. Lett , vol.14 , pp. 5872-8575
    • Moseley, C.K.1    Carlin, S.M.2    Neelamegam, R.3    Hooker, J.M.4
  • 64
    • 0022461409 scopus 로고
    • Pyrazole derivatives. 5. Synthesis and antineoplastic activity of 3-(2-chloroethyl)-3,4-dihydro-4-oxopyrazolo[5,1-d]- 1,2,3,5-tetrazine-8-carboxamide and related compounds
    • Cheng, C.C.; Elslager, E.F.; Werbel, L.M.; Priebe, S.R.; Leopold, W.R., III. Pyrazole derivatives. 5. Synthesis and antineoplastic activity of 3-(2-chloroethyl)-3,4-dihydro-4-oxopyrazolo[5,1-d]- 1,2,3,5-tetrazine-8-carboxamide and related compounds. J. Med. Chem. 1986, 29, 1544-1547.
    • (1986) J. Med. Chem , vol.29 , pp. 1544-1547
    • Cheng, C.C.1    Elslager, E.F.2    Werbel, L.M.3    Priebe, S.R.4    Leopold, W.R.5
  • 65
    • 0032715183 scopus 로고    scopus 로고
    • Pyrrolo [2,1-d][1,2,3,5]tetrazines, a new class of azolotetrazines related to the antitumor drug temozolomide
    • Diana, P.; Barraja, P.; Lauria, A.; Almerico, A.M.; Dattolo, G.; Cirrincione, G. Pyrrolo [2,1-d][1,2,3,5]tetrazines, a new class of azolotetrazines related to the antitumor drug temozolomide. Synthesis-Stuttgart 1999, 12, 2082-2086.
    • (1999) Synthesis-Stuttgart , vol.12 , pp. 2082-2086
    • Diana, P.1    Barraja, P.2    Lauria, A.3    Almerico, A.M.4    Dattolo, G.5    Cirrincione, G.6
  • 67
    • 10444257247 scopus 로고    scopus 로고
    • Synthesis and antiproliferative activity of [1,2,3,5]tetrazino[5,4-a]indoles, a new class of azolo-tetrazinones
    • Barraja, P.; Diana, P.; Lauria, A.; Montalbano, A.; Almerico, A.M.; Dattolo, G.; Cirrincione, G. Synthesis and antiproliferative activity of [1,2,3,5]tetrazino[5,4-a]indoles, a new class of azolo-tetrazinones. Bioorg. Med. Chem. 2005, 13, 295-300.
    • (2005) Bioorg. Med. Chem , vol.13 , pp. 295-300
    • Barraja, P.1    Diana, P.2    Lauria, A.3    Montalbano, A.4    Almerico, A.M.5    Dattolo, G.6    Cirrincione, G.7
  • 68
  • 69
    • 23844475777 scopus 로고    scopus 로고
    • QSAR studies on pyrrolo[2,1-d][1,2,3,5]tetrazinones, a new class of azolotetrazines
    • Tripathi, G.; Mistra, J.P. QSAR studies on pyrrolo[2,1-d][1,2,3,5]tetrazinones, a new class of azolotetrazines. Indian J. Chem. 2005, 44, 1398-1400.
    • (2005) Indian J. Chem , vol.44 , pp. 1398-1400
    • Tripathi, G.1    Mistra, J.P.2
  • 73
    • 68349122700 scopus 로고    scopus 로고
    • Pyrido[2',3':4,5]pyrrolo[2,1-d][1,2,3,5]tetrazine-4(3H)-ones, a new class of temozolomide heteroanalogues
    • Diana, P.; Stagno, A.; Barraja, P.; Montalbano, A.; Carbone, A.; Dattolo, G.; Cirrincione, G. Pyrido[2',3':4,5]pyrrolo[2,1-d][1,2,3,5]tetrazine-4(3H)-ones, a new class of temozolomide heteroanalogues. Arkivoc 2009, 177-186.
    • (2009) Arkivoc , pp. 177-186
    • Diana, P.1    Stagno, A.2    Barraja, P.3    Montalbano, A.4    Carbone, A.5    Dattolo, G.6    Cirrincione, G.7
  • 74
    • 33845693550 scopus 로고    scopus 로고
    • Synthesis of alkyl- 5,8-dimethyl-6-phenyl-5,6-dihydropyrazolo[3,4-f][1,2,3,5]tetrazepin-4(3H)-ones of pharmaceutical interest
    • Maggio, B.; Raffa, D.; Raimondi, M.V.; Plescia, F.; Cascioferro, S.; Daidone, G. Synthesis of alkyl- 5,8-dimethyl-6-phenyl-5,6-dihydropyrazolo[3,4-f][1,2,3,5]tetrazepin-4(3H)-ones of pharmaceutical interest. Arkivoc 2006, 120-126.
    • (2006) Arkivoc , pp. 120-126
    • Maggio, B.1    Raffa, D.2    Raimondi, M.V.3    Plescia, F.4    Cascioferro, S.5    Daidone, G.6
  • 75
    • 34249858102 scopus 로고    scopus 로고
    • Design, synthesis, and quantitative structure-activity relationship study of herbicidal analogues of pyrazolo [5,1-d][1,2,3,5]tetrazin-4(3H)ones
    • Zhu, Y.-Q.; Wu, C.; Li, H.-B.; Zou, X.-M.; Si, X.-K.; Hu, F.-Z.; Yang, H.-Z. Design, synthesis, and quantitative structure-activity relationship study of herbicidal analogues of pyrazolo [5,1-d][1,2,3,5]tetrazin-4(3H)ones. J. Agric. Food Chem. 2007, 55, 1364-1369.
    • (2007) J. Agric. Food Chem , vol.55 , pp. 1364-1369
    • Zhu, Y.-Q.1    Wu, C.2    Li, H.-B.3    Zou, X.-M.4    Si, X.-K.5    Hu, F.-Z.6    Yang, H.-Z.7
  • 76
    • 47749083152 scopus 로고    scopus 로고
    • Design, synthesis and quantitative structure-activity relationship study of herbicidal analogues of pyrazolotetrazinones
    • Zhu, Y.-Q.; Cheng, J.; Zou, X.-M.; Hu, F.-Z.; Xiao, T.-H.; Yang, H.-Z. Design, synthesis and quantitative structure-activity relationship study of herbicidal analogues of pyrazolotetrazinones. Chin. J. Chem. 2008, 28, 1044-1049.
    • (2008) Chin J. Chem , vol.28 , pp. 1044-1049
    • Zhu, Y.-Q.1    Cheng, J.2    Zou, X.-M.3    Hu, F.-Z.4    Xiao, T.-H.5    Yang, H.-Z.6
  • 77
    • 0025361453 scopus 로고
    • Antitumor imidazotetrazines. 20. Preparation of the 8-acid derivative of mitozolomide and its utility in the preparation of active antitumor agents
    • Horspool, K.R.; Stevens, M.F.; Newton, C.G.; Lunt, E.; Walsh, R.J.; Pedgrift, B.L.; Baig, G.U.; Lavelle, F.; Fizames, C. Antitumor imidazotetrazines. 20. Preparation of the 8-acid derivative of mitozolomide and its utility in the preparation of active antitumor agents. J. Med. Chem. 1990, 33, 1393-1399.
    • (1990) J. Med. Chem , vol.33 , pp. 1393-1399
    • Horspool, K.R.1    Stevens, M.F.2    Newton, C.G.3    Lunt, E.4    Walsh, R.J.5    Pedgrift, B.L.6    Baig, G.U.7    Lavelle, F.8    Fizames, C.9
  • 78
    • 78650638916 scopus 로고    scopus 로고
    • Synthesis and antitumor activity of 3-methyl-4-oxo-3, 4-dihydroimidazo [5,1-d][1,2,3,5]tetrazine-8-carboxylates and -carboxamides
    • Liu, D.; Yang, J.-G.; Cheng, J.; Zhao, L.-X. Synthesis and antitumor activity of 3-methyl-4-oxo-3, 4-dihydroimidazo [5,1-d][1,2,3,5]tetrazine-8-carboxylates and -carboxamides. Molecules 2010, 15, 9427-9437.
    • (2010) Molecules , vol.15 , pp. 9427-9437
    • Liu, D.1    Yang, J.-G.2    Cheng, J.3    Zhao, L.-X.4
  • 79
    • 33749236438 scopus 로고    scopus 로고
    • Skin delivery potency and antitumor activities of temozolomide ester prodrugs
    • Suppasansatorn, P.; Wang, G.; Conway, B.R.; Wang, W.; Wang, Y. Skin delivery potency and antitumor activities of temozolomide ester prodrugs. Cancer Lett. 2006, 244, 42-52.
    • (2006) Cancer Lett , vol.244 , pp. 42-52
    • Suppasansatorn, P.1    Wang, G.2    Conway, B.R.3    Wang, W.4    Wang, Y.5
  • 81
    • 0037023579 scopus 로고    scopus 로고
    • Synthesis and antibacterial activity of dual-action agents of a β-lactam antibiotic with cytotoxic agent mitozolomide or temozolomide
    • Wang, Y.; Lambert, P.; Zhao, L.; Wang, D. Synthesis and antibacterial activity of dual-action agents of a β-lactam antibiotic with cytotoxic agent mitozolomide or temozolomide. Eur. J. Med. Chem. 2002, 37, 323-332.
    • (2002) Eur. J. Med. Chem , vol.37 , pp. 323-332
    • Wang, Y.1    Lambert, P.2    Zhao, L.3    Wang, D.4
  • 82
    • 84891819979 scopus 로고    scopus 로고
    • The temozolomide derivative 2T-P400 inhibits glioma growth via administration route of intravenous injection
    • Li, R.; Tang, D.; Zhang, J.; Wu, J.; Wang, L.; Dong, J. The temozolomide derivative 2T-P400 inhibits glioma growth via administration route of intravenous injection. J. Neurooncol. 2014, 116, 25-30.
    • (2014) J. Neurooncol , vol.116 , pp. 25-30
    • Li, R.1    Tang, D.2    Zhang, J.3    Wu, J.4    Wang, L.5    Dong, J.6
  • 87
    • 84867949152 scopus 로고    scopus 로고
    • Antitumour imidazotetrazines. Synthesis and chemistry of 4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide (nor-temozolomide): An intermediate for the preparation of the antitumour drug temozolomide and analogues, avoiding the use of isocyan
    • Cousin, D.; Stevens, M.F.G.; Hummersone, M.G. Antitumour imidazotetrazines. Synthesis and chemistry of 4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide (nor-temozolomide): An intermediate for the preparation of the antitumour drug temozolomide and analogues, avoiding the use of isocyan. Med. Chem. Comm. 2012, 3, 1419-1422.
    • (2012) Med. Chem. Comm , vol.3 , pp. 1419-1422
    • Cousin, D.1    Stevens, M.F.G.2    Hummersone, M.G.3
  • 88
    • 33646469000 scopus 로고    scopus 로고
    • Polar, functionalized guanine-O6 derivatives resistant to repair by O6-alkylguanine-DNA alkyltransferase: Implications for the design of DNA-modifying drugs
    • Pletsas, D.; Wheelhouse, R.T.; Pletsa, V.; Nicolaou, A.; Jenkins, T.C.; Bibby, M.C.; Kyrtopoulos, S.A. Polar, functionalized guanine-O6 derivatives resistant to repair by O6-alkylguanine-DNA alkyltransferase: implications for the design of DNA-modifying drugs. Eur. J. Med. Chem. 2006, 41, 330-339.
    • (2006) Eur. J. Med. Chem , vol.41 , pp. 330-339
    • Pletsas, D.1    Wheelhouse, R.T.2    Pletsa, V.3    Nicolaou, A.4    Jenkins, T.C.5    Bibby, M.C.6    Kyrtopoulos, S.A.7
  • 89
  • 91
    • 0023805191 scopus 로고
    • Methyl mercapturate episulfonium ion: A model reactive metabolite of dihaloethanes
    • Henkel, J.G.; Amato, G.S. Methyl mercapturate episulfonium ion: a model reactive metabolite of dihaloethanes. J. Med. Chem. 1988, 31, 1279-1282.
    • (1988) J. Med. Chem , vol.31 , pp. 1279-1282
    • Henkel, J.G.1    Amato, G.S.2
  • 95
    • 84884239964 scopus 로고    scopus 로고
    • Synthesis and quantitative structure-activity relationship of imidazotetrazine prodrugs with activity independent of O6-methylguanine-DNA-methyltransferase, DNA mismatch repair, and p53
    • Pletsas, D.; Garelnabi, E.A.E.; Li, L.; Phillips, R.M.; Wheelhouse, R.T. Synthesis and quantitative structure-activity relationship of imidazotetrazine prodrugs with activity independent of O6-methylguanine-DNA-methyltransferase, DNA mismatch repair, and p53. J. Med. Chem. 2013, 56, 7120-7132
    • (2013) J. Med. Chem , vol.56 , pp. 7120-7132
    • Pletsas, D.1    Garelnabi, E.A.E.2    Li, L.3    Phillips, R.M.4    Wheelhouse, R.T.5


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