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Volumn 50, Issue 13, 2007, Pages 3046-3053

Design and synthesis of classical and nonclassical 6-arylthio-2,4-diamino- 5-ethylpyrrolo[2,3-d]pyrimidines as antifolates

Author keywords

[No Author keywords available]

Indexed keywords

4 [(2,4 DIAMINO 5 ETHYL 7H PYRROLO[2,3 D]PYRIMIDIN 6 YL)SULFANYL]BENZOIC ACID; 5 ETHYL 6 (1 NAPHTHYLSULFANYL) 7H PYRROLO[2,3 D]PYRIMIDINE 2,4 DIAMINE; 5 ETHYL 6 (2 NAPHTHYLSULFANYL) 7H PYRROLO[2,3 D]PYRIMIDINE 2,4 DIAMINE; 5 ETHYL 6 (8 QUINOLINYLSULFANYL) 7H PYRROLO[2,3 D]PYRIMIDINE 2,4 DIAMINE; 5 ETHYL 6 (PHENYLSULFANYL) 7H PYRROLO[2,3 D]PYRIMIDINE 2,4 DIAMINE; 5 ETHYL 6 [(3 METHOXYPHENYL)SULFANYL] 7H PYRROLO[2,3 D]PYRIMIDINE 2,4 DIAMINE; 5 ETHYL 6 [(4 METHOXYPHENYL)SULFANYL] 7 H PYRROLO[2,3 D]PYRIMIDINE 2,4 DIAMINE; 5 ETHYL 6 [(4 NITROPHENYL)SULFANYL] 7H PYRROLO[2,3 D]PYRIMIDINE 2,4 DIAMINE; 6 [(2,4 DICHLOROPHENYL)SULFANYL] 5 ETHYL 7H PYRROLO[2,3 D]PYRIMIDINE 2,4 DIAMINE; 6 [(2,5 DIMETHOXYPHENYL)SULFANYL] 5 ETHYL 7H PYRROLO[2,3 D] PYRIMIDINE 2,4 DIAMINE; 6 [(2,6 DICHLOROPHENYL)SULFANYL] 5 ETHYL 7H PYRROLO[2,3 D]PYRIMIDINE 2,4 DIAMINE; 6 [(2,6 DIMETHYLPHENYL)SULFANYL] 5 ETHYL 7H PYRROLO[2,3 D]PYRIMIDINE 2,4 DIAMINE; 6 [(3 CHLOROPHENYL)SULFANYL] 5 ETHYL 7H PYRROLO[2,3 D]PYRIMIDINE 2,4 DIAMINE; 6 [(3,4 DICHLOROPHENYL)SULFANYL] 5 ETHYL 7H PYRROLO[2,3 D]PYRIMIDINE 2,4 DIAMINE; 6 [(4 BROMOPHENYL)SULFANYL] 5 ETHYL 7H PYRROLO[2,3 D]PYRIMIDINE 2,4 DIAMINE; 6 [(4 CHLOROPHENYL)SULFANYL] 5 ETHYL 7H PYRROLO[2,3 D]PYRIMIDINE 2,4 DIAMINE; 6 THIO 2,4 DIAMINO 5 ETHYLPYRROLO[2,3 D]PYRIMIDINE DERIVATIVE; ANTINEOPLASTIC AGENT; DIHYDROFOLATE REDUCTASE INHIBITOR; FOLIC ACID ANTAGONIST; METHOTREXATE; N [4 [(2,4 DIAMINO 5 ETHYL 7H PYRROLO[2,3 D]PYRIMIDIN 6 YL)SULFANYL]BENZOYL]GLUTAMIC ACID; N [4 [(5 ETHYL 2 AMINO 3,4 DIHYDRO 4 OXO 7H PYRROLO[2,3 D]PYRIMIDIN 6 YL)THIO]BENZOYL]GLUTAMATE; TRIMETHOPRIM; UNCLASSIFIED DRUG;

EID: 34347248076     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm070165j     Document Type: Article
Times cited : (274)

References (21)
  • 1
    • 0025970198 scopus 로고
    • The Renewed Potential for Folate Antagonists in Contemporary Cancer Chemotherapy
    • Berman, E. M.; Werbel, L. M. The Renewed Potential for Folate Antagonists in Contemporary Cancer Chemotherapy. J. Med. Chem. 1991, 34, 479-485.
    • (1991) J. Med. Chem , vol.34 , pp. 479-485
    • Berman, E.M.1    Werbel, L.M.2
  • 2
    • 0024780585 scopus 로고
    • Chemistry and Biological Activity of Antifolates
    • Ellis, G. P, West, G. B, Eds, Elsevier Science Publishers: Amsterdam
    • Rosowsky, A. Chemistry and Biological Activity of Antifolates. In Progress in Medicinal Chemistry; Ellis, G. P., West, G. B., Eds.; Elsevier Science Publishers: Amsterdam, 1989; pp 1-252.
    • (1989) Progress in Medicinal Chemistry , pp. 1-252
    • Rosowsky, A.1
  • 3
    • 0001181244 scopus 로고    scopus 로고
    • Classical and Nonclassical Antifolates as Potential Antitumor, Antipneumocystis and Antitoxoplasma Agents
    • Gangjee, A.; Elzein, E.; Kothare, M.; Vasudevan, A. Classical and Nonclassical Antifolates as Potential Antitumor, Antipneumocystis and Antitoxoplasma Agents. Curr. Pharm. Des. 1996, 2, 263-280.
    • (1996) Curr. Pharm. Des , vol.2 , pp. 263-280
    • Gangjee, A.1    Elzein, E.2    Kothare, M.3    Vasudevan, A.4
  • 4
    • 28544447614 scopus 로고    scopus 로고
    • Gangjee, A.; Lin, X.; Kisliuk, R. L.; McGuire, J. J. Synthesis of N-{4-[(2,4-Diamino-5-methyl-4,7-dihydro-3H-pyrrolo[2,3-d] pyrimidin-6-yl)thio]benzoyl}-L-glutamic Acid and N-{4-[(2-Amino- 4-oxo-5-methyl-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl)thio] benzoyl}-L-glutamic Acid as Dual Inhibitors of Dihydrofolate Reductase and Thymidylate Synthase and as Potential Antitumor Agents. J. Med. Chem. 2005, 48, 7215-7222.
    • Gangjee, A.; Lin, X.; Kisliuk, R. L.; McGuire, J. J. Synthesis of N-{4-[(2,4-Diamino-5-methyl-4,7-dihydro-3H-pyrrolo[2,3-d] pyrimidin-6-yl)thio]benzoyl}-L-glutamic Acid and N-{4-[(2-Amino- 4-oxo-5-methyl-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl)thio] benzoyl}-L-glutamic Acid as Dual Inhibitors of Dihydrofolate Reductase and Thymidylate Synthase and as Potential Antitumor Agents. J. Med. Chem. 2005, 48, 7215-7222.
  • 5
    • 34347267520 scopus 로고    scopus 로고
    • We thank the Developmental Therapeutics Program of the National Cancer Institute for performing the in vitro anticancer evaluation
    • We thank the Developmental Therapeutics Program of the National Cancer Institute for performing the in vitro anticancer evaluation.
  • 6
    • 34347213958 scopus 로고    scopus 로고
    • Tripos Inc., 1699 South Handley Rd, Suite 303, St. Louis, MO 63144.
    • Tripos Inc., 1699 South Handley Rd, Suite 303, St. Louis, MO 63144.
  • 7
    • 0022479337 scopus 로고
    • Synthesis and Antifolate Activity of 5-Methyl-5-deaza Analogs of Aminopterin, MTX, Folic Acid, and N10-Methyl Folic Acid
    • Piper, J. R.; McCaleb, G. S.; Montgomery, J. A.; Kisliuk, R. L.; Gaumont, Y.; Sirotnak, F. M. Synthesis and Antifolate Activity of 5-Methyl-5-deaza Analogs of Aminopterin, MTX, Folic Acid, and N10-Methyl Folic Acid. J. Med. Chem. 1986, 29, 1080-1087.
    • (1986) J. Med. Chem , vol.29 , pp. 1080-1087
    • Piper, J.R.1    McCaleb, G.S.2    Montgomery, J.A.3    Kisliuk, R.L.4    Gaumont, Y.5    Sirotnak, F.M.6
  • 9
    • 0344393780 scopus 로고    scopus 로고
    • Resistance to Antifolates
    • Zhao, R.; Goldman, I. D. Resistance to Antifolates. Oncogene 2003, 22, 7431-7457.
    • (2003) Oncogene , vol.22 , pp. 7431-7457
    • Zhao, R.1    Goldman, I.D.2
  • 10
    • 0011087873 scopus 로고
    • Sirotnak, F. M, Burchall, J. J, Ensminger, W, Montgomery, J. A, Eds, Academic Press: Orlando, FL
    • Werbel, L. M. In Folate Antagonists as Therapeutic Agents; Sirotnak, F. M., Burchall, J. J., Ensminger, W., Montgomery, J. A., Eds.; Academic Press: Orlando, FL, 1984; Vol. 1, pp 261.
    • (1984) Folate Antagonists as Therapeutic Agents , vol.1 , pp. 261
    • Werbel, L.M.1
  • 11
    • 0031037171 scopus 로고    scopus 로고
    • Drug Treatment of HIV-Related Opportunistic Infections
    • Klepser, M. E.; Klepser, T. B. Drug Treatment of HIV-Related Opportunistic Infections. Drugs 1997, 53, 40-73.
    • (1997) Drugs , vol.53 , pp. 40-73
    • Klepser, M.E.1    Klepser, T.B.2
  • 12
    • 3042594465 scopus 로고    scopus 로고
    • Synthesis, and Biological Evaluation of 2,4-Diamino-5-methyl-6-substituted-pyrrolo[2,3-d] pyrimidines as Dihydrofolate Reductase Inhibitors
    • Gangjee, A.; Lin, X.; Queener, S. F. Design, Synthesis, and Biological Evaluation of 2,4-Diamino-5-methyl-6-substituted-pyrrolo[2,3-d] pyrimidines as Dihydrofolate Reductase Inhibitors. J. Med. Chem. 2004, 47, 3689-3692.
    • (2004) J. Med. Chem , vol.47 , pp. 3689-3692
    • Gangjee, A.1    Lin, X.2    Queener, S.3    Design, F.4
  • 13
    • 0029804033 scopus 로고    scopus 로고
    • 2-Amino-4-oxo-5-substituted-pyrrolo[2,3-d]pyrimidines as Non-classical Antifolate Inhibitors of Thymidylate Synthase
    • Gangjee, A.; Mavandadi, F.; Kisliuk, R. L.; McGuire, J. J.; Queener, S. F. 2-Amino-4-oxo-5-substituted-pyrrolo[2,3-d]pyrimidines as Non-classical Antifolate Inhibitors of Thymidylate Synthase. J. Med. Chem. 1996, 39, 4563-4568.
    • (1996) J. Med. Chem , vol.39 , pp. 4563-4568
    • Gangjee, A.1    Mavandadi, F.2    Kisliuk, R.L.3    McGuire, J.J.4    Queener, S.F.5
  • 14
    • 0028823792 scopus 로고    scopus 로고
    • Taylor, E. C.; Patel, H. H.; Jun, J.-G. A One-Step Ring Transformation/Ring Annulation Approach to Pyrrolo[2,3-d]pyrimidines. A New Synthesis of the Potent Dihydrofolate Reductase Inhibitor TNP-351. J. Org. Chem. 1995, 60, 6684-6687.
    • Taylor, E. C.; Patel, H. H.; Jun, J.-G. A One-Step Ring Transformation/Ring Annulation Approach to Pyrrolo[2,3-d]pyrimidines. A New Synthesis of the Potent Dihydrofolate Reductase Inhibitor TNP-351. J. Org. Chem. 1995, 60, 6684-6687.
  • 15
    • 0037171724 scopus 로고    scopus 로고
    • Synthesis of N-[4-[1-Ethyl-2-(2,4-diaminofuro[2,3-d]pyrimidin-5-yl)ethyl]benzoyl] -L-glutamic Acid as an Antifolate
    • Gangjee, A.; Zeng, Y.; McGuire, J. J.; Kisliuk, R. L. Synthesis of N-[4-[1-Ethyl-2-(2,4-diaminofuro[2,3-d]pyrimidin-5-yl)ethyl]benzoyl] -L-glutamic Acid as an Antifolate. J. Med. Chem. 2002, 45, 1942-1948.
    • (2002) J. Med. Chem , vol.45 , pp. 1942-1948
    • Gangjee, A.1    Zeng, Y.2    McGuire, J.J.3    Kisliuk, R.L.4
  • 16
    • 0022007266 scopus 로고
    • Molecular and Karyological Analysis of Methotrexate-Resistant and - Sensitive Human Leukemic CCRF-CEM Cells
    • Mini, E.; Srimatkandata, S.; Medina, W. D.; Moroson, B. A.; Carman, M. D.; Bertino, J. R. Molecular and Karyological Analysis of Methotrexate-Resistant and - Sensitive Human Leukemic CCRF-CEM Cells. Cancer Res. 1985, 45, 317-325.
    • (1985) Cancer Res , vol.45 , pp. 317-325
    • Mini, E.1    Srimatkandata, S.2    Medina, W.D.3    Moroson, B.A.4    Carman, M.D.5    Bertino, J.R.6
  • 17
  • 18
    • 0025817134 scopus 로고
    • Decreased Folylpolyglutamate Synthetase Activity as a Mechanism of Methotrexate Resistance in CCRF-CEM Human Leukemia Sublines
    • McCloskey, D. E.; McGuire, J. J.; Russell, C. A.; Rowan, B. G.; Bertino, J. R.; Pizzorno, G.; Mini, E. Decreased Folylpolyglutamate Synthetase Activity as a Mechanism of Methotrexate Resistance in CCRF-CEM Human Leukemia Sublines. J. Biol. Chem. 1991, 266, 6181-6187.
    • (1991) J. Biol. Chem , vol.266 , pp. 6181-6187
    • McCloskey, D.E.1    McGuire, J.J.2    Russell, C.A.3    Rowan, B.G.4    Bertino, J.R.5    Pizzorno, G.6    Mini, E.7
  • 19
    • 0000622838 scopus 로고
    • The Ability of Purine and Thymidine Derivatives and of Glycine to Support the Growth of Mammalian Cells in Culture
    • Hakala, M. T.; Taylor, E. The Ability of Purine and Thymidine Derivatives and of Glycine to Support the Growth of Mammalian Cells in Culture. J. Biol. Chem. 1959, 234, 126-128.
    • (1959) J. Biol. Chem , vol.234 , pp. 126-128
    • Hakala, M.T.1    Taylor, E.2
  • 20
    • 0018731964 scopus 로고
    • Thymidine Induced Perturbations in Ribonucleoside and Deoxyribonucleoside Triphosphate Pools in Human Leukemic CCRF-CEM Cells
    • Grindey, G. B.; Wang, M. C.; Kinahan, J. J. Thymidine Induced Perturbations in Ribonucleoside and Deoxyribonucleoside Triphosphate Pools in Human Leukemic CCRF-CEM Cells. Mol. Pharmacol. 1979, 16, 601-606.
    • (1979) Mol. Pharmacol , vol.16 , pp. 601-606
    • Grindey, G.B.1    Wang, M.C.2    Kinahan, J.J.3
  • 21
    • 0001206491 scopus 로고
    • Continuous Culture of Lymphoblasts from Peripheral Blood of a Child with Acute Leukemia
    • Foley, G. F.; Lazarus, H.; Farber, S.; Uzman, B. G.; Boone, B. A.; McCarthy, R. E. Continuous Culture of Lymphoblasts from Peripheral Blood of a Child with Acute Leukemia. Cancer 1965, 18, 522-529.
    • (1965) Cancer , vol.18 , pp. 522-529
    • Foley, G.F.1    Lazarus, H.2    Farber, S.3    Uzman, B.G.4    Boone, B.A.5    McCarthy, R.E.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.