메뉴 건너뛰기




Volumn 47, Issue 27, 2004, Pages 6893-6901

Synthesis of classical, three-carbon-bridged 5-substituted furo[2,3-d]pyrimidine and 6-substituted pyrrolo[2,3-d]pyrimidine analogues as antifolates

Author keywords

[No Author keywords available]

Indexed keywords

2,6 DIAMINOPYRIMIDIN 4 ONE; ALPHA CHLOROMETHYL KETONE DERIVATIVE; AMINOPTERIN; BENZOIC ACID DERIVATIVE; DEOXYCYTIDINE; FOLIC ACID ANTAGONIST; FOLINIC ACID; FURO[2,3 D]PYRIMIDINE DERIVATIVE; HYPOXANTHINE; KETONE DERIVATIVE; METHYL 4 BROMOBENZOIC ACID DERIVATIVE; N [4 [3 (2 AMINO 3,4 DIHYDRO 4 OXO 7H PYRROLO[2,3 D]PYRIMIDIN 6 YL)PROPYL]BENZOYL]GLUTAMIC ACID; N [4 [3 (2,4 DIAMINOFURO[2,3 D]PYRIMIDIN 5 YL)PROPYL]BENZOYL]GLUTAMIC ACID; PEMETREXED; PYRIMIDINE DERIVATIVE; PYRROLO[2,3 D]PYRIMIDINE DERIVATIVE; THYMIDINE; UNCLASSIFIED DRUG;

EID: 11144231233     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm040123k     Document Type: Article
Times cited : (63)

References (33)
  • 2
    • 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
  • 3
    • 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
  • 4
    • 0001181244 scopus 로고    scopus 로고
    • Classical and nonclassical antifolates as potential antitumor, anti-pneumocystis and antitoxoplasma agents
    • Gangjee, A.; Elzein, E.; Kothare, M.; Vasudevan, A. Classical and Nonclassical Antifolates as Potential Antitumor, Anti-pneumocystis and Antitoxoplasma Agents. Curr. Pharm. Design 1996, 2, 263-280.
    • (1996) Curr. Pharm. Design , vol.2 , pp. 263-280
    • Gangjee, A.1    Elzein, E.2    Kothare, M.3    Vasudevan, A.4
  • 5
    • 0029153212 scopus 로고
    • Effect of bridge region variation on antifolate and antitumor activity of classical 5-substituted 2,4-diaminofuro[2,3-d]pyrimidines
    • Gangjee, A.; Devraj, R.; McGuire, J. J.; Kisliuk, R. L. Effect of Bridge Region Variation on Antifolate and Antitumor Activity of Classical 5-Substituted 2,4-Diaminofuro[2,3-d]pyrimidines. J. Med. Chem. 1995, 38, 3798-3805.
    • (1995) J. Med. Chem. , vol.38 , pp. 3798-3805
    • Gangjee, A.1    Devraj, R.2    McGuire, J.J.3    Kisliuk, R.L.4
  • 6
    • 0034632877 scopus 로고    scopus 로고
    • Effect of C9-methyl substitution and C8-C9 conformational restriction on antifolate and antitumor activity of classical 5-substituted 2,4-diaminofuro[2,3-d]pyrimidines
    • Gangjee, A.; Zeng, Y.; McGuire, J. J.; Kisliuk, R. L. Effect of C9-Methyl Substitution and C8-C9 Conformational restriction on Antifolate and Antitumor Activity of Classical 5-Substituted 2,4-Diaminofuro[2,3-d]pyrimidines. J. Med. Chem. 2000, 43, 3125-3133.
    • (2000) J. Med. Chem. , vol.43 , pp. 3125-3133
    • Gangjee, A.1    Zeng, Y.2    McGuire, J.J.3    Kisliuk, R.L.4
  • 7
    • 0037171724 scopus 로고    scopus 로고
    • Synthesis of N-[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-[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
  • 8
    • 11144244468 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.
  • 9
    • 0027432378 scopus 로고
    • Conformational analysis of human dihydrofolate reductase inhibitor complexes: Crystal structure determination of wild-type and F31 mutant binary and ternary inhibitor complexes
    • Ayling, J. E., Nair, M. G., Baugh, C. M., Eds.; Plenum Press: New York
    • Cody, V.; Wojtczak, A.; Kalman, T. I.; Friesheim, J. H.; Blakley, R. L. Conformational Analysis of Human Dihydrofolate Reductase Inhibitor Complexes: Crystal Structure Determination of Wild-Type and F31 Mutant Binary and Ternary Inhibitor Complexes. In Advances in Experimental Medicine and Biology, Chemistry, and Biology of Pteridines and Folates; Ayling, J. E., Nair, M. G., Baugh, C. M., Eds.; Plenum Press: New York, 1993; Vol. 338, pp 481-486.
    • (1993) Advances in Experimental Medicine and Biology, Chemistry, and Biology of Pteridines and Folates , vol.338 , pp. 481-486
    • Cody, V.1    Wojtczak, A.2    Kalman, T.I.3    Friesheim, J.H.4    Blakley, R.L.5
  • 10
    • 0026062272 scopus 로고
    • Novel pyrrolo[2,3-d]pyrimidine antifolates: Synthesis and antitumor activities
    • Miwa, T.; Hitaka, T.; Akimoto, H.; Nomura, H. Novel Pyrrolo[2,3-d] pyrimidine Antifolates: Synthesis and Antitumor Activities. J. Med. Chem. 1991, 34, 555-560.
    • (1991) J. Med. Chem. , vol.34 , pp. 555-560
    • Miwa, T.1    Hitaka, T.2    Akimoto, H.3    Nomura, H.4
  • 11
    • 0034687229 scopus 로고    scopus 로고
    • Design, synthesis, and X-ray crystal structure of a potent dual inhibitor of thymidylate synthase and dihydrofolate reductase as an antitumor agent
    • Gangjee, A.; Yu, J.; McGuire, J. J.; Cody, V.; Galitsky, N.; Kisliuk, R. L.; Queener, S. F. Design, Synthesis, and X-ray Crystal Structure of a Potent Dual Inhibitor of Thymidylate Synthase and Dihydrofolate Reductase as an Antitumor Agent. J. Med. Chem. 2000, 43, 3837-3851.
    • (2000) J. Med. Chem. , vol.43 , pp. 3837-3851
    • Gangjee, A.1    Yu, J.2    McGuire, J.J.3    Cody, V.4    Galitsky, N.5    Kisliuk, R.L.6    Queener, S.F.7
  • 12
    • 0026494947 scopus 로고
    • A dideazatetrahydrofolate analogue lacking a chiral center at C6 N-[4-[2-(2-ammo-3,4-dihydro-4-oxo-7H-pyrrolo[2,3-d]pyrimidine-5-yl)ethyl] benzoyl]-L-glutamic acid, is an inhibitor of thymidylate synthase
    • Taylor, E. C.; Kuhnt, D.; Shih, C.; Rinzel, S. M.; Grindey, G. B.; Barredo, J.; Lannatipour, M.; Moran, R. A Dideazatetrahydrofolate Analogue Lacking a Chiral Center at C6, N-[4-[2-(2-Ammo-3,4-dihydro-4-oxo-7H-pyrrolo[2,3- d]pyrimidine-5-yl)ethyl]benzoyl]-L-glutamic Acid, Is an Inhibitor of Thymidylate Synthase. J. Med. Chem. 1992, 35, 4450-4454.
    • (1992) J. Med. Chem. , vol.35 , pp. 4450-4454
    • Taylor, E.C.1    Kuhnt, D.2    Shih, C.3    Rinzel, S.M.4    Grindey, G.B.5    Barredo, J.6    Lannatipour, M.7    Moran, R.8
  • 13
    • 0034737311 scopus 로고    scopus 로고
    • The crystal structure of thymidylate synthase from pneumocystis carinii reveals a fungal insert important for drug design
    • Anderson, A. C.; Perry, K. M.; Freymann, D. M. and Stroud, R. M. The Crystal Structure of Thymidylate Synthase From Pneumocystis carinii Reveals a Fungal Insert Important for Drug Design. J. Mol. Biol. 2000, 297, 645-657.
    • (2000) J. Mol. Biol. , vol.297 , pp. 645-657
    • Anderson, A.C.1    Perry, K.M.2    Freymann, D.M.3    Stroud, R.M.4
  • 15
    • 0344689721 scopus 로고
    • Studies directed toward a total synthesis of nucleoside Q. The annulation of 2,4-diamino-pyrimidin-4-one pyrimidin-4-one with (α-halo carbonyls to form pyrrolo[2,3-d]pyrimidines and furo[2,3-d]pyrimidines
    • Secrist, J. A., III; Liu, P. S. Studies Directed Toward a Total Synthesis of Nucleoside Q. The Annulation of 2,4-Diamino-pyrimidin-4-one pyrimidin-4-one with (α-Halo Carbonyls To Form Pyrrolo[2,3-d]pyrimidines and Furo[2,3-d]pyrimidines. J. Org. Chem. 1978, 43, 3937-3941.
    • (1978) J. Org. Chem. , vol.43 , pp. 3937-3941
    • Secrist III, J.A.1    Liu, P.S.2
  • 16
    • 11144232733 scopus 로고    scopus 로고
    • Classical 2,4-diamino-5-substituted furo[2,3-d]pyrimidme and 2-amino-4-oxo-6-substituted pyrrolo[2,3-d]pyrimidine on antifolate activity
    • Milstien, S., Kapatos, G., Levine, R. A., Shane, B., Eds.; Kluwer Academic Publishers: Boston
    • Gangjee, A.; Yang, J.; McGuire, J. J.; Kisliuk, R. L. Classical 2,4-Diamino-5-substituted Furo[2,3-d]pyrimidme and 2-Amino-4-oxo-6-substituted Pyrrolo[2,3-d]pyrimidine on Antifolate Activity. In Chemistry and Biochemistry of Pteridines and Folates; Milstien, S., Kapatos, G., Levine, R. A., Shane, B., Eds.; Kluwer Academic Publishers: Boston, 2002; pp 445-450.
    • (2002) Chemistry and Biochemistry of Pteridines and Folates , pp. 445-450
    • Gangjee, A.1    Yang, J.2    McGuire, J.J.3    Kisliuk, R.L.4
  • 17
    • 0025358902 scopus 로고
    • A convergent synthesis of 5, 10-dideaza-5,6,7,8-tetrahydrofolic acid and 5,10-dideaza-5,6,7,8-tetrahydrohomofolic acid. An effective principle for carbonyl group activation
    • Taylor, E. C.; Harrington, P. M. A Convergent Synthesis of 5, 10-Dideaza-5,6,7,8-tetrahydrofolic Acid and 5,10-Dideaza-5,6,7,8- tetrahydrohomofolic Acid. An Effective Principle for Carbonyl Group Activation. J. Org. Chem. 1990, 55, 3222-3227.
    • (1990) J. Org. Chem. , vol.55 , pp. 3222-3227
    • Taylor, E.C.1    Harrington, P.M.2
  • 18
    • 0033043416 scopus 로고    scopus 로고
    • Total synthesis of (±)-nisamycin
    • Wipf, P.; Coish, P. D. G. Total Synthesis of (±)-Nisamycin. J. Org. Chem. 1999, 64, 5053-5061.
    • (1999) J. Org. Chem. , vol.64 , pp. 5053-5061
    • Wipf, P.1    Coish, P.D.G.2
  • 20
    • 0030633340 scopus 로고    scopus 로고
    • Thymidylate synthase as a target for growth inhibition in methotrexate-sensitive and -resistant human head and neck cancer and leukemia cell lines
    • McGuire, J. J.; Magee, K. J.; Russell, C. A.; Canestrari, J. M. Thymidylate Synthase as a Target for Growth Inhibition in Methotrexate-Sensitive and -Resistant Human Head and Neck Cancer and Leukemia Cell Lines. Oncology Res. 1997, 9, 139-147.
    • (1997) Oncology Res. , vol.9 , pp. 139-147
    • McGuire, J.J.1    Magee, K.J.2    Russell, C.A.3    Canestrari, J.M.4
  • 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
  • 22
    • 0022007266 scopus 로고
    • Molecular and karyological analysis of methotrexate-resistant and -sensitive human leukemic CCRF-CEM cells
    • Mini, E.; Srimatkandada, 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    Srimatkandada, S.2    Medina, W.D.3    Moroson, B.A.4    Carman, M.D.5    Bertino, J.R.6
  • 24
    • 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
  • 25
    • 0033537838 scopus 로고    scopus 로고
    • Impaired membrane transport in methotrexate-resistant CCRF-CEM cells involves early translation termination and increased turnover of a mutant reduced folate carrier
    • Wong, S. C.; Zhang, L.; Witt, T. L.; Proefke, S. A.; Bhushan, A.; Matherly, L. H. Impaired Membrane Transport in Methotrexate-Resistant CCRF-CEM Cells Involves Early Translation Termination and Increased Turnover of a Mutant Reduced Folate Carrier. J. Biol. Chem. 1999, 274, 10388-10394.
    • (1999) J. Biol. Chem. , vol.274 , pp. 10388-10394
    • Wong, S.C.1    Zhang, L.2    Witt, T.L.3    Proefke, S.A.4    Bhushan, A.5    Matherly, L.H.6
  • 26
    • 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
  • 27
    • 0344708478 scopus 로고    scopus 로고
    • Anticancer antifolates: Current status and future directions
    • McGuire, J. J. Anticancer Antifolates: Current Status and Future Directions. Curr. Pharm. Design 2003, 9, 2593-2613.
    • (2003) Curr. Pharm. Design , vol.9 , pp. 2593-2613
    • McGuire, J.J.1
  • 28
    • 11144247798 scopus 로고    scopus 로고
    • note
    • We thank the Developmental Therapeutics Program of the National Cancer Institute for performing the in vitro anticancer evaluation.
  • 29
    • 0017672047 scopus 로고
    • Diastereoisomers of 5,10-methylene-5,6,7,8-tetrahydropteroyl-D-glutamic Acid
    • Kisliuk, R. L.; Strumpf, D.; Gaumont, Y.; Leary, R. P.; Plante, L. Diastereoisomers of 5,10-Methylene-5,6,7,8-tetrahydropteroyl-D-glutamic Acid. J. Med. Chem. 1977, 20, 1531-1533.
    • (1977) J. Med. Chem. , vol.20 , pp. 1531-1533
    • Kisliuk, R.L.1    Strumpf, D.2    Gaumont, Y.3    Leary, R.P.4    Plante, L.5
  • 30
    • 0001530879 scopus 로고
    • The enzymatic synthesis of thymidylate. Early step in the purification of thymidylate synthetase of escherichia coli
    • Wahba, A. J.; Friedkin, M. The Enzymatic Synthesis of Thymidylate. Early Step in the Purification of Thymidylate Synthetase of Escherichia coli. J. Biol. Chem. 1962, 237, 3794-3801.
    • (1962) J. Biol. Chem. , vol.237 , pp. 3794-3801
    • Wahba, A.J.1    Friedkin, M.2
  • 31
    • 0024333859 scopus 로고
    • Expression of human thymidylate synthase in escherichia coli
    • Davissson, V. J.; Sirawaraporn, W.; Santi, D. V. Expression of Human Thymidylate Synthase in Escherichia coli. J. Biol. Chem. 1989, 264, 9145-9148.
    • (1989) J. Biol. Chem. , vol.264 , pp. 9145-9148
    • Davissson, V.J.1    Sirawaraporn, W.2    Santi, D.V.3
  • 33
    • 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


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.