메뉴 건너뛰기




Volumn 56, Issue 17, 2013, Pages 7120-7132

Synthesis and quantitative structure-activity relationship of imidazotetrazine prodrugs with activity independent of O6-methylguanine-DNA- methyltransferase, DNA mismatch repair, and p53

Author keywords

[No Author keywords available]

Indexed keywords

3 [2 [(4 METHOXY 2 NITROPHENYL)(METHYL)AMINO]ETHYL] 4OXO 3,4 DIHYDROIMIDAZO[5,1 D][1,2,3,5]TETRAZINE 8 CARBOXAMIDE; 3 [2 [METHYL(4 METHYL 3 NITROPHENYL)AMINO]ETHYL] 4 OXO 3,4 DIHYDROIMIDAZO[5,1 D][1,2,3,5]TETRAZINE 8 CARBOXAMIDE; 6 O METHYLGUANINE; ANTINEOPLASTIC AGENT; CISPLATIN; DNA METHYLTRANSFERASE; GUANINE; IMIDAZOTETRAZINE; ION; METHYLTRANSFERASE; PROTEIN P53; TEMOZOLOMIDE; TERT BUTYL 2 [8 CARBAMOYL 4 OXOIMIDAZO(5,1 D)(1,2,3,5) TETRAZIN 3(4H) YL]ETHYL(4 CHLOROPHENYL) CARBAMATE; UNCLASSIFIED DRUG;

EID: 84884239964     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm401121k     Document Type: Article
Times cited : (16)

References (39)
  • 2
    • 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
  • 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
    • 0023605735 scopus 로고
    • Antitumor Imidazotetrazines 13. 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.; Newton, C.; Lunt, E.; Fizames, C.; Lavelle, F. Antitumor Imidazotetrazines 13. 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    Newton, C.11    Lunt, E.12    Fizames, C.13    Lavelle, F.14
  • 5
    • 0013859673 scopus 로고
    • Imidazoles. II. 5(or 4)-(Monosubstituted triazeno)imidazole-4(or 5)-carboxamides
    • Shealy, Y. F.; Krauth, C. A. Imidazoles. II. 5(or 4)-(Monosubstituted triazeno)imidazole-4(or 5)-carboxamides J. Med. Chem. 1966, 9, 35-38
    • (1966) J. Med. Chem. , vol.9 , pp. 35-38
    • Shealy, Y.F.1    Krauth, C.A.2
  • 6
    • 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. H. 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.H.4
  • 7
    • 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 J. Chem. Soc., Chem. Commun. 1993, 1177-1179
    • (1993) J. Chem. Soc., Chem. Commun. , pp. 1177-1179
    • Wheelhouse, R.T.1    Stevens, M.F.G.2
  • 8
    • 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
  • 11
    • 33845280234 scopus 로고
    • Ab Initio Studies of Triazenes in Relation to Experimental Findings
    • Schmiedekamp, A.; Smith, R. H.; Michejda, C. J. Ab Initio Studies of Triazenes in Relation to Experimental Findings J. Org. Chem. 1988, 53, 3433-3436
    • (1988) J. Org. Chem. , vol.53 , pp. 3433-3436
    • Schmiedekamp, A.1    Smith, R.H.2    Michejda, C.J.3
  • 13
    • 33748507110 scopus 로고    scopus 로고
    • Antitumour Imidazotetrazines. Part 36. Conversion of 5-aminoimidazole-4- carboxamide to Imidazo-[5,1-d]-1,2,3,5-tetrazin4(3H)-ones and Imidazo-[1,5-a]-1,3,5-triazin4(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-aminoimidazole-4- carboxamide to Imidazo-[5,1-d]-1,2,3,5-tetrazin4(3H)-ones and Imidazo-[1,5-a]-1,3,5-triazin4(3H)-ones Related in Structure to the Antitumour Agents Temozolomide and Mitozolomide J. Chem. Soc., Perkin Trans. 1 1998, 1669-1676
    • (1998) J. Chem. Soc., Perkin Trans. 1 , pp. 1669-1676
    • Wang, Y.1    Wheelhouse, R.T.2    Zhao, L.3    Langnel, D.A.F.4    Stevens, M.F.G.5
  • 16
    • 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
  • 22
    • 0028906786 scopus 로고
    • Some Practical Considerations and Applications of the National-Cancer-Institute in-Vitro Anticancer Drug Discovery Screen
    • Boyd, M. R.; Pauli, K. D. Some Practical Considerations and Applications of the National-Cancer-Institute in-Vitro Anticancer Drug Discovery Screen Drug Development Res. 1995, 34, 91-109
    • (1995) Drug Development Res. , vol.34 , pp. 91-109
    • Boyd, M.R.1    Pauli, K.D.2
  • 23
    • 0027933603 scopus 로고
    • Topoisomerase II Inhibition and Cytotoxicity of the Anthrapyrazoles DuP 937 and DuP 941 (Losoxantrone) in the National Cancer Institute Preclinical Antitumor Drug Discovery
    • Leteurtre, F.; Kohlhagen, G.; Paull, K. D.; Pommier, Y. Topoisomerase II Inhibition and Cytotoxicity of the Anthrapyrazoles DuP 937 and DuP 941 (Losoxantrone) in the National Cancer Institute Preclinical Antitumor Drug Discovery J. Nat. Cancer Inst. 1994, 86, 1239-1244
    • (1994) J. Nat. Cancer Inst. , vol.86 , pp. 1239-1244
    • Leteurtre, F.1    Kohlhagen, G.2    Paull, K.D.3    Pommier, Y.4
  • 24
    • 37549024231 scopus 로고    scopus 로고
    • Thiopurines in Current Medical Practice: Molecular Mechanisms and Contributions to Therapy-related Cancer
    • Karran, P.; Attard, N. Thiopurines in Current Medical Practice: Molecular Mechanisms and Contributions to Therapy-related Cancer Nat. Rev. Cancer 2008, 8, 24-36
    • (2008) Nat. Rev. Cancer , vol.8 , pp. 24-36
    • Karran, P.1    Attard, N.2
  • 25
    • 34547116188 scopus 로고    scopus 로고
    • Thiopurines, DNA Damage, DNA Repair and Therapy-related Cancer
    • Karran, P. Thiopurines, DNA Damage, DNA Repair and Therapy-related Cancer Br. Med. Bull. 2006, 79-80, 153-170
    • (2006) Br. Med. Bull. , vol.79-80 , pp. 153-170
    • Karran, P.1
  • 26
    • 84884229315 scopus 로고    scopus 로고
    • accessed March 7
    • Genecards (The Human Genome Compendium) http://www.genecards.org, accessed March 7, 2013.
    • (2013)
  • 28
    • 0242663968 scopus 로고    scopus 로고
    • The p38 Mitogen-Activated Protein Kinase Pathway Links the DNA Mismatch Repair System to the G2 Checkpoint and to Resistance to Chemotherapeutic DNA-Methylating Agents
    • Hirose, Y.; Katayama, M.; Stokoe, D.; Haas-Kogan, D. A.; Berger, M. S.; Pieper, R. O. The p38 Mitogen-Activated Protein Kinase Pathway Links the DNA Mismatch Repair System to the G2 Checkpoint and to Resistance to Chemotherapeutic DNA-Methylating Agents Mol. Cell. Biol. 2003, 8306-8315
    • (2003) Mol. Cell. Biol. , pp. 8306-8315
    • Hirose, Y.1    Katayama, M.2    Stokoe, D.3    Haas-Kogan, D.A.4    Berger, M.S.5    Pieper, R.O.6
  • 29
    • 79959682172 scopus 로고    scopus 로고
    • Certain Imidazotetrazines Escape O 6-Methylguanine-DNA Methyltransferase and Mismatch Repair
    • Zhang, J.; Stevens, M. F. G.; Hummersone, M.; Madhusudan, S.; Laughton, C. A.; Bradshaw, T. D. Certain Imidazotetrazines Escape O 6-Methylguanine-DNA Methyltransferase and Mismatch Repair Oncology 2011, 80, 195-207
    • (2011) Oncology , vol.80 , pp. 195-207
    • Zhang, J.1    Stevens, M.F.G.2    Hummersone, M.3    Madhusudan, S.4    Laughton, C.A.5    Bradshaw, T.D.6
  • 30
    • 0032694518 scopus 로고    scopus 로고
    • Pharmacologic Disruption of Base Excision Repair Sensitizes Mismatch Repair-deficient and -proficient Colon Cancer Cells to Methylating Agents
    • Liu, L.; Taverna, P.; Whitacre, C. M.; Chatterjee, S.; Gerson, S. L. Pharmacologic Disruption of Base Excision Repair Sensitizes Mismatch Repair-deficient and -proficient Colon Cancer Cells to Methylating Agents Clin. Cancer Res. 1999, 5, 2908-2917
    • (1999) Clin. Cancer Res. , vol.5 , pp. 2908-2917
    • Liu, L.1    Taverna, P.2    Whitacre, C.M.3    Chatterjee, S.4    Gerson, S.L.5
  • 33
    • 84981869142 scopus 로고
    • Über 1.2-Dithia-cyclopentene, IX Alkalische Spaltung des 1.2-Dithia-cyclopentenon-(3)-Rings
    • Boberg, F. Über 1.2-Dithia-cyclopentene, IX Alkalische Spaltung des 1.2-Dithia-cyclopentenon-(3)-Rings Leibigs 1965, 683, 132-148
    • (1965) Leibigs , vol.683 , pp. 132-148
    • Boberg, F.1
  • 35
    • 20144374430 scopus 로고    scopus 로고
    • Synthesis of Some 1,2,4-Triazoles as Potential Antifungal Agents
    • Siddiqui, A. A.; Arora, A.; Siddiqui, N.; Misra, A. Synthesis of Some 1,2,4-Triazoles as Potential Antifungal Agents Indian J. Chem. B 2005, 44, 838-841
    • (2005) Indian J. Chem. B , vol.44 , pp. 838-841
    • Siddiqui, A.A.1    Arora, A.2    Siddiqui, N.3    Misra, A.4
  • 36
    • 70349135530 scopus 로고    scopus 로고
    • Solvent-Promoted and -Controlled Aza-Michael Reaction with Aromatic Amines
    • De, K.; Legros, J.; Crousse, B.; Bonnet-Delpon, D. Solvent-Promoted and -Controlled Aza-Michael Reaction with Aromatic Amines J. Org. Chem. 2009, 74, 6260-6265
    • (2009) J. Org. Chem. , vol.74 , pp. 6260-6265
    • De, K.1    Legros, J.2    Crousse, B.3    Bonnet-Delpon, D.4
  • 37
    • 69249199738 scopus 로고    scopus 로고
    • An Efficient ZrCl4 Catalyzed Aza-Michael Addition Reaction: Synthesis of C-Linked Carbo beta(3)-Amino Acids
    • Damera, K.; Reddy, K. L.; Sharma, G. V. M. An Efficient ZrCl4 Catalyzed Aza-Michael Addition Reaction: Synthesis of C-Linked Carbo beta(3)-Amino Acids Lett. Org. Chem. 2009, 6) 151-155
    • (2009) Lett. Org. Chem. , Issue.6 , pp. 151-155
    • Damera, K.1    Reddy, K.L.2    Sharma, G.V.M.3
  • 38
    • 84888198944 scopus 로고
    • Luminescence of Hydrazide Derivatives Containing Rare Earth Elements
    • Kotera, M. Luminescence of Hydrazide Derivatives Containing Rare Earth Elements Nippon Kagaku Kaishi 1979, 1279-1281
    • (1979) Nippon Kagaku Kaishi , pp. 1279-1281
    • Kotera, M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.