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Volumn 47, Issue 1, 2004, Pages 240-253

Folate-Synthesizing Enzyme System as Target for Development of Inhibitors and Inhibitor Combinations against Candida albicans - Synthesis and Biological Activity of New 2,4-Diaminopyrimidines and 4′-Substituted 4-Aminodiphenyl Sulfones

Author keywords

[No Author keywords available]

Indexed keywords

2,4 DIAMINO 5 (2,6 DICHLOROBENZYLOXY)PYRIMIDINE; 2,4 DIAMINO 5 (3,4 DICHLOROBENZYLOXY)PYRIMIDINE; 2,4 DIAMINO 5 (4 METHOXYBENZYLOXY)PYRIMIDINE; 2,4 DIAMINO 5 [3 METHOXY 4 (3 PHENYLPROPOXY)BENZYLOXY]PYRIMIDINE; 2,4 DIAMINOPYRIMIDINE DERIVATIVE; 5 (2 CHLOROBENZYLOXY) 2,4 DIAMINOPYRIMIDINE; 5 (4 BENZYLOXYBENZYLOXY) 2,4 DIAMINOPYRIMIDINE; 5 (4 BROMO 1 NAPHTHYLMETHYLOXY) 2,4 DIAMINOPYRIMIDINE; 5 (4 TERT BUTYLBENZYLOXY) 2,4 DIAMINOPYRIMIDINE; 5 BENZYLOXY 2,4 DIAMINOPYRIMIDINE; CYCLOSPORIN A; DAPSONE; DIAMINO 5 (1 NAPHTHYLMETHYLOXY)PYRIMIDINE; DIHYDROFOLATE REDUCTASE; DIHYDROPTEROIC ACID SYNTHASE; FLUCONAZOLE; FOLIC ACID; HH 133; HH 135; HH 136; HH 154; K 130; K 220; KC 1308; OXIDOREDUCTASE; RO 12 6099; RO 17 3279; SULFONE DERIVATIVE; SYNTHETASE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

EID: 0346731227     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm030931w     Document Type: Article
Times cited : (138)

References (58)
  • 1
    • 0028568541 scopus 로고
    • The emerging fungal threat
    • Sternberg, S. The emerging fungal threat. Science 1994, 266, 1632-1634.
    • (1994) Science , vol.266 , pp. 1632-1634
    • Sternberg, S.1
  • 2
    • 0025853376 scopus 로고
    • Invasive candida infections. Evolution of a fungal pathogen
    • Edwards, J. F. Invasive candida infections. Evolution of a fungal pathogen. N. Engl. J. Med. 1991, 324, 1060-1062.
    • (1991) N. Engl. J. Med. , vol.324 , pp. 1060-1062
    • Edwards, J.F.1
  • 3
    • 0022116795 scopus 로고
    • Fungemia in a cancer hospital: Changing frequency, earlier onset, and results of therapy
    • Horn, R.; Wong, B.; Kiehn, T. E.; Armstrong, D. Fungemia in a cancer hospital: Changing frequency, earlier onset, and results of therapy. Rev. Infect. Dis. 1985, 7, 646-655.
    • (1985) Rev. Infect. Dis. , vol.7 , pp. 646-655
    • Horn, R.1    Wong, B.2    Kiehn, T.E.3    Armstrong, D.4
  • 4
    • 0004281374 scopus 로고
    • Wissenschaftliche Verlagsgesellschaft: Stuttgart, Germany
    • Mutschler, E. Arzneimittelwirkungen; Wissenschaftliche Verlagsgesellschaft: Stuttgart, Germany, 1991.
    • (1991) Arzneimittelwirkungen
    • Mutschler, E.1
  • 6
    • 0347853293 scopus 로고
    • Effects of drugs on lipids and membrane integrity of fungi
    • Jackson, G. G., Schlumberger, H. D., Zeilers, H.-J., Eds.; Bayer Centenary Symp., Washington, DC; Springer-Verlag: Heidelberg, Germany
    • Georgopapadakou, N. H. Effects of drugs on lipids and membrane integrity of fungi, In Perspectives in Antiinfective Therapy; Jackson, G. G., Schlumberger, H. D., Zeilers, H.-J., Eds.; Bayer Centenary Symp., Washington, DC, 1988; Springer-Verlag: Heidelberg, Germany, 1989; pp 100-111.
    • (1988) Perspectives in Antiinfective Therapy , pp. 100-111
    • Georgopapadakou, N.H.1
  • 7
    • 0024159379 scopus 로고
    • Mechanism of action and biochemical selectivity of allylamine antimycotic agents
    • Ryder, N. S. Mechanism of action and biochemical selectivity of allylamine antimycotic agents. Ann. N. Y. Acad. Sci. 1988, 544, 208-220.
    • (1988) Ann. N. Y. Acad. Sci. , vol.544 , pp. 208-220
    • Ryder, N.S.1
  • 9
    • 0020106085 scopus 로고
    • Trimethoprim-sulfamethoxazole: An assessment of more than 12 years use
    • Salter, A. J. Trimethoprim-sulfamethoxazole: An assessment of more than 12 years use. Rev. Infect. Dis. 1982, 4, 196-236.
    • (1982) Rev. Infect. Dis. , vol.4 , pp. 196-236
    • Salter, A.J.1
  • 10
    • 0345961900 scopus 로고
    • The metabolism of plasmodia and the chemotherapy of malaria infections
    • Wood, C., Ed., Academic Press: London
    • Hitchings, G. H. The metabolism of plasmodia and the chemotherapy of malaria infections. In Tropical Medicine from Romance to Reality; Wood, C., Ed., Academic Press: London, 1978; pp 79-98.
    • (1978) Tropical Medicine from Romance to Reality , pp. 79-98
    • Hitchings, G.H.1
  • 11
    • 0346593205 scopus 로고
    • Tropical diseases, recent drug developments with special emphasis on antimalarial and antileprosy drugs
    • Timmerman, H., Ed., Elsevier: Amsterdam
    • Seydel, J. K.; Wiese, M.; Kansy, M.; Schaper, K.-J.; Walter, R. Tropical diseases, recent drug developments with special emphasis on antimalarial and antileprosy drugs. In Trends in Drug Research; Timmerman, H., Ed., Elsevier: Amsterdam, 1990; Vol. 13, pp 109-131.
    • (1990) Trends in Drug Research , vol.13 , pp. 109-131
    • Seydel, J.K.1    Wiese, M.2    Kansy, M.3    Schaper, K.-J.4    Walter, R.5
  • 12
    • 0346593206 scopus 로고
    • New inhibitors of plasmodial folate synthesis - Comparison of cell-free, whole cell and in vivo activities for single drugs and drug combinations
    • Curtius, H.-C., Ghisla, S., Blau, N., Eds.; Walter de Gruyter & Co,: Berlin, New York
    • Wiese, M.; Kansy, M.; Kunz, B.; Schaper, K.-J.; Seydel, J. K.; Walter, R.; Chandra, S. New inhibitors of plasmodial folate synthesis-Comparison of cell-free, whole cell and in vivo activities for single drugs and drug combinations. Proceedings in Chemistry and Biology of Pteridines 1989; Curtius, H.-C., Ghisla, S., Blau, N., Eds.; Walter de Gruyter & Co,: Berlin, New York, 1990; pp 535-546.
    • (1990) Proceedings in Chemistry and Biology of Pteridines 1989 , pp. 535-546
    • Wiese, M.1    Kansy, M.2    Kunz, B.3    Schaper, K.-J.4    Seydel, J.K.5    Walter, R.6    Chandra, S.7
  • 14
    • 0024990148 scopus 로고
    • Characterization of dihydrofolate reductase of Pneumocystis carinii and Toxoplasma gondii
    • Kovacs, J. A.; Allegra, C. J.; Masur, H. Characterization of dihydrofolate reductase of Pneumocystis carinii and Toxoplasma gondii. Exp. Parasitol. 1990, 71, 60-68.
    • (1990) Exp. Parasitol. , vol.71 , pp. 60-68
    • Kovacs, J.A.1    Allegra, C.J.2    Masur, H.3
  • 16
    • 0028837274 scopus 로고
    • Structure-activity and structure selectivity studies on diaminoquinazolines and other inhibitors of Pneumocystis carinii and Toxoplasma gondii dihydrofolate reductase
    • Rosowsky, A.; Hynes, J. R.; Queener, S. F. Structure-activity and structure selectivity studies on diaminoquinazolines and other inhibitors of Pneumocystis carinii and Toxoplasma gondii dihydrofolate reductase. Antimicrob. Agents Chemother. 1995, 339, 79-86.
    • (1995) Antimicrob. Agents Chemother. , vol.339 , pp. 79-86
    • Rosowsky, A.1    Hynes, J.R.2    Queener, S.F.3
  • 17
    • 0029990447 scopus 로고    scopus 로고
    • 2,4-Diamino-5-deaza-6-substituted pyrido[2,3-d]pyrimidine antifolates as potent and selective nonclassical inhibitors of dihydrofolate reductase
    • Gangjee, A.; Vasudevan, A.; Queener, S. F.; Kisliuk, R. L. 2,4-Diamino-5-deaza-6-substituted pyrido[2,3-d]pyrimidine antifolates as potent and selective nonclassical inhibitors of dihydrofolate reductase. J. Med. Chem. 1996, 39, 1438-1446.
    • (1996) J. Med. Chem. , vol.39 , pp. 1438-1446
    • Gangjee, A.1    Vasudevan, A.2    Queener, S.F.3    Kisliuk, R.L.4
  • 18
    • 0031059045 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of nonclassical 2,4-diamino-5-methylpyrido-[2,3-d]pyrimidines with novel side chain substituents as potential inhibitors of dihydrofolate reductase
    • Gangjee, A.; Vasudevan, A.; Queener, S. F. Synthesis and biological evaluation of nonclassical 2,4-diamino-5-methylpyrido-[2,3-d]pyrimidines with novel side chain substituents as potential inhibitors of dihydrofolate reductase. J. Med. Chem. 199~7, 40, 479-485.
    • (1997) J. Med. Chem. , vol.40 , pp. 479-485
    • Gangjee, A.1    Vasudevan, A.2    Queener, S.F.3
  • 20
    • 0034644146 scopus 로고    scopus 로고
    • Development of a lead inhibitor for the A16V+S108T mutant of dihydrofolate reductase from the Cycloguanil-resistant strain (T9/94) of Plasmodium falciparum
    • Yuthavong, Y.; Vilainvan, T.; Chareonsethakul, N.; Kamchonwongpalsan, S. ; Sirawaraporn, W.; Quarell, R.; Lowe, G. Development of a lead inhibitor for the A16V+S108T mutant of dihydrofolate reductase from the Cycloguanil-resistant strain (T9/94) of Plasmodium falciparum. J. Med. Chem. 2000, 43, 2738-2744.
    • (2000) J. Med. Chem. , vol.43 , pp. 2738-2744
    • Yuthavong, Y.1    Vilainvan, T.2    Chareonsethakul, N.3    Kamchonwongpalsan, S.4    Sirawaraporn, W.5    Quarell, R.6    Lowe, G.7
  • 23
    • 0346593205 scopus 로고
    • Tropical diseases with special emphasis on antimalarial and antileprosy drugs
    • Seydel, J. K.; Wiese, M.; Kansy, M.; Schaper, K.-J.; Walter, R., Tropical diseases with special emphasis on antimalarial and antileprosy drugs. Pharmacochem. Libr. 1990, 13, 109-131.
    • (1990) Pharmacochem. Libr. , vol.13 , pp. 109-131
    • Seydel, J.K.1    Wiese, M.2    Kansy, M.3    Schaper, K.-J.4    Walter, R.5
  • 24
    • 0025055471 scopus 로고
    • In vitro and in vivo experiments with the new inhibitor of Mycobacterium leprae Brodimoprim alone and in combination with Dapsone
    • Seydel J. K.; Wempe, E. G.; Rosenfeld, M.; Jagannathan, R.; Mahadevan, P. R., Dhople, A. M., In vitro and in vivo experiments with the new inhibitor of Mycobacterium leprae Brodimoprim alone and in combination with Dapsone. Arzneim.-Forsch. / Drug Res. 1990, 40, 69-75.
    • (1990) Arzneim.-Forsch. / Drug Res. , vol.40 , pp. 69-75
    • Seydel, J.K.1    Wempe, E.G.2    Rosenfeld, M.3    Jagannathan, R.4    Mahadevan, P.R.5    Dhople, A.M.6
  • 25
    • 0017587594 scopus 로고
    • 2,4-Diamino-5-(pyridylmethyl)-pyrimidine als potentielle Chemotherapeutica
    • Kompis, I.; Muller, W.; Boehni, E.; Then, R.; Montavon, M. 2,4-Diamino-5-(pyridylmethyl)-pyrimidine als potentielle Chemotherapeutica. Eur. J. Med. Chem. 1977, 12, 531-536.
    • (1977) Eur. J. Med. Chem. , vol.12 , pp. 531-536
    • Kompis, I.1    Muller, W.2    Boehni, E.3    Then, R.4    Montavon, M.5
  • 26
    • 0015290021 scopus 로고
    • Synthesis of trimethoprim variations
    • Stogryn, E. L. Synthesis of trimethoprim variations. J. Med. Chem. 1972, 15, 200-201.
    • (1972) J. Med. Chem. , vol.15 , pp. 200-201
    • Stogryn, E.L.1
  • 27
    • 0347853292 scopus 로고
    • (Beecham Group Ltd.) U.S. Patent 4,719,562 1979
    • Ponsford, R. J. (Beecham Group Ltd.) U.S. Patent 4,719,562 1979, Chem. Abstr. 1980, 92, 145802; Chem. Abstr. 1980, 92, 76538.
    • (1980) Chem. Abstr. , vol.92 , pp. 145802
    • Ponsford, R.J.1
  • 28
    • 0345961901 scopus 로고
    • Ponsford, R. J. (Beecham Group Ltd.) U.S. Patent 4,719,562 1979, Chem. Abstr. 1980, 92, 145802; Chem. Abstr. 1980, 92, 76538.
    • (1980) Chem. Abstr. , vol.92 , pp. 76538
  • 29
    • 0347223179 scopus 로고
    • 2,4-Diamino-5-benzyl-pyrimidines as inhibitors of dihydrofolate reductase
    • Brodbeck U., Ed.; Verlag Chemie: Weinheim, Germany
    • Kompis, I.; Then, R.; Wick, A.; Montavon, M. 2,4-Diamino-5-benzyl-pyrimidines as inhibitors of dihydrofolate reductase. In Enzyme Inhibitors; Brodbeck, U., Ed.; Verlag Chemie: Weinheim, Germany, 1980; pp 177-189.
    • (1980) Enzyme Inhibitors , pp. 177-189
    • Kompis, I.1    Then, R.2    Wick, A.3    Montavon, M.4
  • 30
    • 0014351943 scopus 로고
    • Folic acid analogues. I. p-{(2,4-Diamino-5-pyrimidinyl)methyll amino}-benzoyl-L-glutamic acid and related compounds
    • Weinstock, L. T.; O'Brien, D. E.; Cheng, C. C. Folic acid analogues. I. p-{(2,4-Diamino-5-pyrimidinyl)methyll amino}-benzoyl-L-glutamic acid and related compounds. J. Med. Chem. 1968, 11, 1238-1244.
    • (1968) J. Med. Chem. , vol.11 , pp. 1238-1244
    • Weinstock, L.T.1    O'Brien, D.E.2    Cheng, C.C.3
  • 31
    • 0000300447 scopus 로고
    • A new synthesis of 5-benzylpyrimidines
    • Steinbuck, P.; Baltzly, R.; Hood, H. M. A new synthesis of 5-benzylpyrimidines. J. Org. Chem. 1963, 28, 1983-1988.
    • (1963) J. Org. Chem. , vol.28 , pp. 1983-1988
    • Steinbuck, P.1    Baltzly, R.2    Hood, H.M.3
  • 33
    • 0024210114 scopus 로고
    • Synthese und antimykobakterielle Wirkung einiger lipophil substituierter 2,4-Diamino-5-benzylpyrimidine
    • Hachtel, G.; Haller, R.; Seydel, J. K. Synthese und antimykobakterielle Wirkung einiger lipophil substituierter 2,4-Diamino-5-benzylpyrimidine. Arzneim. -Forsch. / Drug Res. 1988, 38, 1778-1783.
    • (1988) Arzneim. -Forsch. / Drug Res. , vol.38 , pp. 1778-1783
    • Hachtel, G.1    Haller, R.2    Seydel, J.K.3
  • 34
    • 0019294312 scopus 로고    scopus 로고
    • Studies on antimalarials. I. Synthesis and antimalarial effects of 2,4-diamino-5-substituted aminopyrimidines and 2,4-diamino-6-methyl-5-substituted aminopyrimidines
    • Zhang, X.-P.; Zhang, X.-J.; Zheng, X.-H.; Chen, L.; Dai, Z.-R. Studies on antimalarials. I. Synthesis and antimalarial effects of 2,4-diamino-5-substituted aminopyrimidines and 2,4-diamino-6-methyl-5-substituted aminopyrimidines. Yaoxue Xuebao (Acta Pharm. Sin.) 1980, 15 (12), 711-18. Chem. Abstr. 95, 150575.
    • (1980) Yaoxue Xuebao (Acta Pharm. Sin.) , vol.15 , Issue.12 , pp. 711-18
    • Zhang, X.-P.1    Zhang, X.-J.2    Zheng, X.-H.3    Chen, L.4    Dai, Z.-R.5
  • 35
    • 0019294312 scopus 로고    scopus 로고
    • Zhang, X.-P.; Zhang, X.-J.; Zheng, X.-H.; Chen, L.; Dai, Z.-R. Studies on antimalarials. I. Synthesis and antimalarial effects of 2,4-diamino-5-substituted aminopyrimidines and 2,4-diamino-6-methyl-5-substituted aminopyrimidines. Yaoxue Xuebao (Acta Pharm. Sin.) 1980, 15 (12), 711-18. Chem. Abstr. 95, 150575.
    • Chem. Abstr. , vol.95 , pp. 150575
  • 36
    • 0014487775 scopus 로고
    • Irreversible enzyme inhibitors CLI. Active site-directed irreversible inhibitors of dihydrofolate reductase derived from 5-(p-aminophenylbutyl)-2,4-diaminopyrimidines with a terminal sulfonyl fluoride
    • Baker, B. R.; Meyer, R. B., Jr. Irreversible enzyme inhibitors CLI. Active site-directed irreversible inhibitors of dihydrofolate reductase derived from 5-(p-aminophenylbutyl)-2,4-diaminopyrimidines with a terminal sulfonyl fluoride. J. Med. Chem. 1969, 12, 224-227.
    • (1969) J. Med. Chem. , vol.12 , pp. 224-227
    • Baker, B.R.1    Meyer Jr., R.B.2
  • 37
    • 0000486839 scopus 로고
    • The ultraviolet absorption spectra of pyrimidines and pteridines
    • Cavalieri, L. F.; Bendich, A. J. The ultraviolet absorption spectra of pyrimidines and pteridines. J. Am. Chem. Soc. 1950, 72, 2587-2594.
    • (1950) J. Am. Chem. Soc. , vol.72 , pp. 2587-2594
    • Cavalieri, L.F.1    Bendich, A.J.2
  • 38
    • 0347223180 scopus 로고
    • Pyrimidines. I. The synthesis of some 5-hydroxypyrimidines
    • Hull, R. Pyrimidines. I. The synthesis of some 5-hydroxypyrimidines. J. Chem. Soc. 1956, 2033-2035.
    • (1956) J. Chem. Soc. , pp. 2033-2035
    • Hull, R.1
  • 39
    • 0002938232 scopus 로고
    • Application of the Elbs persulfate oxidation for the preparation of 5-hydroxypyrimidines
    • Hurst, D. T. Application of the Elbs persulfate oxidation for the preparation of 5-hydroxypyrimidines. Aust. J. Chem. 1983, 36, 1285-1289.
    • (1983) Aust. J. Chem. , vol.36 , pp. 1285-1289
    • Hurst, D.T.1
  • 40
    • 0025641242 scopus 로고
    • Improved methods for the purification of enzymes of the folate pathway in Escherichia coli. 1. Chromatographic methods
    • Bartels, R.; Bock, L. Improved methods for the purification of enzymes of the folate pathway in Escherichia coli. 1. Chromatographic methods. J. Chromatogr. 1990, 523, 53-60.
    • (1990) J. Chromatogr. , vol.523 , pp. 53-60
    • Bartels, R.1    Bock, L.2
  • 41
    • 0023501974 scopus 로고
    • Multiple regression analysis of antimalarial activities of sulfones and sulfonamides in cell-free systems and principal component analysis to compare with antibacterial activities
    • Wiese, M.; Seydel, J. K.; Pieper, H.; Krüger, G.; Noll, K. R.; Keck, J. Multiple regression analysis of antimalarial activities of sulfones and sulfonamides in cell-free systems and principal component analysis to compare with antibacterial activities. Quant. Struct.-Act. Relat. 1987, 6, 164-172.
    • (1987) Quant. Struct.-Act. Relat. , vol.6 , pp. 164-172
    • Wiese, M.1    Seydel, J.K.2    Pieper, H.3    Krüger, G.4    Noll, K.R.5    Keck, J.6
  • 42
    • 0022416802 scopus 로고
    • Multiple regression and principal component analysis of antibacterial activities of sulfones and sulfonamides in whole cell and cell-free systems of various DDS sensitive and resistant bacterial strains
    • Coats, E. A.; Cordes, H.-P.; Kulkarni, V. M.; Richter, M.; Schaper, K.-J.; Wiese, M.; Seydel, J. K. Multiple regression and principal component analysis of antibacterial activities of sulfones and sulfonamides in whole cell and cell-free systems of various DDS sensitive and resistant bacterial strains. Quant. Struct.-Act. Relat. 1985, 4, 99-109.
    • (1985) Quant. Struct.-Act. Relat. , vol.4 , pp. 99-109
    • Coats, E.A.1    Cordes, H.-P.2    Kulkarni, V.M.3    Richter, M.4    Schaper, K.-J.5    Wiese, M.6    Seydel, J.K.7
  • 43
    • 0015268762 scopus 로고
    • Kinetics and mechanism of action of trimethoprim and sulfonamides alone and in combination upon E. coli
    • Seydel, J. K.; Wempe, E.; Miller, G. H.; Miller, L. Kinetics and mechanism of action of trimethoprim and sulfonamides alone and in combination upon E. coli. Chemotherapy 1972, 17, 217-258.
    • (1972) Chemotherapy , vol.17 , pp. 217-258
    • Seydel, J.K.1    Wempe, E.2    Miller, G.H.3    Miller, L.4
  • 44
    • 0019980632 scopus 로고
    • Bacterial growth kinetics of "Mycobacterium lufu" in the presence and absence of various drugs alone and in combination. A model for the development of combined chemotherapy against M. leprae?
    • Seydel, J. K.; Wempe, E. Bacterial growth kinetics of "Mycobacterium lufu" in the presence and absence of various drugs alone and in combination. A model for the development of combined chemotherapy against M. leprae? Int. J. Leprosy 1982, 50, 20-30.
    • (1982) Int. J. Leprosy , vol.50 , pp. 20-30
    • Seydel, J.K.1    Wempe, E.2
  • 45
    • 0017049714 scopus 로고
    • Activity of selected 2,4-diaminoquinazolines against C. albicans in vitro
    • Hynes, J. B.; Hough, L. V.; Smith, A. B.; Gale, G. R. Activity of selected 2,4-diaminoquinazolines against C. albicans in vitro. Proc. Soc. Exp. Biol. Med. 1976, 153, 230-232.
    • (1976) Proc. Soc. Exp. Biol. Med. , vol.153 , pp. 230-232
    • Hynes, J.B.1    Hough, L.V.2    Smith, A.B.3    Gale, G.R.4
  • 46
    • 0020378492 scopus 로고
    • Receptor-based design of dihydrofolate reductase inhibitors: Comparison of crystallographically determined enzyme binding with enzyme affinity in a series of carboxy-substituted trimethoprim analogues
    • Kuyper, L.; Roth, B.; Baccanari, D.; Ferone, R.; Bedell, C. R.; Campness, J. N.; Stammers, D. K.; Dann, J. G.; Norrington, F. E. A.; Baker, D. J.; Goodford, P. J. Receptor-based design of dihydrofolate reductase inhibitors: Comparison of crystallographically determined enzyme binding with enzyme affinity in a series of carboxy-substituted trimethoprim analogues. J. Med. Chem. 1982, 25, 1120-1123.
    • (1982) J. Med. Chem. , vol.25 , pp. 1120-1123
    • Kuyper, L.1    Roth, B.2    Baccanari, D.3    Ferone, R.4    Bedell, C.R.5    Campness, J.N.6    Stammers, D.K.7    Dann, J.G.8    Norrington, F.E.A.9    Baker, D.J.10    Goodford, P.J.11
  • 47
    • 0026716030 scopus 로고
    • Synthesis of new 2,4-diamino-5-benzylpyrimidines active against various bacterial species
    • Kansy, M.; Seydel, J. K.; Wiese, M.; Haller, R. Synthesis of new 2,4-diamino-5-benzylpyrimidines active against various bacterial species. Eur. J. Med. Chem. 1992, 27, 237-244.
    • (1992) Eur. J. Med. Chem. , vol.27 , pp. 237-244
    • Kansy, M.1    Seydel, J.K.2    Wiese, M.3    Haller, R.4
  • 48
    • 0023595183 scopus 로고
    • Design of a new 2,4-diamino-benzylpyrimidine as inhibitor of bacterial dihydrofolate reductase assisted by molecular graphics
    • Czaplinski, K.-H.; Kansy, M.; Seydel, J. K.; Haller, R. Design of a new 2,4-diamino-benzylpyrimidine as inhibitor of bacterial dihydrofolate reductase assisted by molecular graphics. Quant. Struct.-Act. Relat. 1987, 6, 70-72.
    • (1987) Quant. Struct.-Act. Relat. , vol.6 , pp. 70-72
    • Czaplinski, K.-H.1    Kansy, M.2    Seydel, J.K.3    Haller, R.4
  • 49
    • 0028825294 scopus 로고
    • New benzylpyrimidines: Inhibitors of DHFR from various species. QSAR-, CoMFA- and PC analysis
    • Czaplinski, K.-H.; Hänsel, W.; Wiese, M.; Seydel, J. K. New benzylpyrimidines: Inhibitors of DHFR from various species. QSAR-, CoMFA- and PC analysis. Eur. J. Med. Chem. 1995, 30, 779-787.
    • (1995) Eur. J. Med. Chem. , vol.30 , pp. 779-787
    • Czaplinski, K.-H.1    Hänsel, W.2    Wiese, M.3    Seydel, J.K.4
  • 50
    • 0029871727 scopus 로고    scopus 로고
    • New antifolate 4,4′-diaminodiphenyl sulfones substituted 2,4-diamino-5-benzylpyrimidines. Proof of their dual mode of action and autosynergism
    • Wiese, M.; Schmalz, D.; Seydel, J. K. New antifolate 4,4′ -diaminodiphenyl sulfones substituted 2,4-diamino-5-benzylpyrimidines. Proof of their dual mode of action and autosynergism. Arch. Pharm. Pharm. Med. Chem. 1996, 329, 161-168.
    • (1996) Arch. Pharm. Pharm. Med. Chem. , vol.329 , pp. 161-168
    • Wiese, M.1    Schmalz, D.2    Seydel, J.K.3
  • 52
    • 0029133585 scopus 로고
    • Selective inhibitors of Candida albicans dihydrofolate reductase: Activity and selectivity of 5-(arylthio)-2,4-diaminoquinazolines
    • Chan, J. H.; Hong, J. S.; Kuyper, L. F.; Baccanari, D. P.; Joyner, S. S. ; Tansik, R. L.; Boytos, C. M.; Rudolph, S. K. Selective inhibitors of Candida albicans dihydrofolate reductase: Activity and selectivity of 5-(arylthio)-2,4-diaminoquinazolines. J. Med. Chem. 1995, 38, 3608-3616.
    • (1995) J. Med. Chem. , vol.38 , pp. 3608-3616
    • Chan, J.H.1    Hong, J.S.2    Kuyper, L.F.3    Baccanari, D.P.4    Joyner, S.S.5    Tansik, R.L.6    Boytos, C.M.7    Rudolph, S.K.8
  • 54
    • 0345961898 scopus 로고
    • Personal communication
    • Kompis, I. Personal communication, 1989.
    • (1989)
    • Kompis, I.1
  • 55
    • 0001762868 scopus 로고
    • 2,4-Diamino-5-(4-methyl-5-hydroxyethylthiazoliumchloride)methylpyrimidine
    • Huber, W. 2,4-Diamino-5-(4-methyl-5-hydroxyethylthiazoliumchloride)methylpyrimidine. J. Am. Chem. Soc. 1943, 65, 2222-2226.
    • (1943) J. Am. Chem. Soc. , vol.65 , pp. 2222-2226
    • Huber, W.1
  • 56
    • 0004238799 scopus 로고
    • VEB Deutscher Verlag der Wissenschaften, Berlin
    • Organikum, VEB Deutscher Verlag der Wissenschaften, Berlin, 1981; pp 600-604.
    • (1981) Organikum , pp. 600-604
  • 57
    • 0023832506 scopus 로고
    • 2,4-Diamino-5-benzylpyrimidines and analogues as antibacterial agents. 9. Lipophilic trimethoprim analogues as antigonococcal agents
    • Roth, B.; Baccanari, D. P.; Sigel, C. W.; Hubbell, J. P.; Eaddy, J.; Kao, J. C.; Grace, M. E.; Rauckman, B. S. 2,4-Diamino-5-benzylpyrimidines and analogues as antibacterial agents. 9. Lipophilic trimethoprim analogues as antigonococcal agents. J. Med. Chem. 1988, 31, 122-129.
    • (1988) J. Med. Chem. , vol.31 , pp. 122-129
    • Roth, B.1    Baccanari, D.P.2    Sigel, C.W.3    Hubbell, J.P.4    Eaddy, J.5    Kao, J.C.6    Grace, M.E.7    Rauckman, B.S.8
  • 58
    • 0006983939 scopus 로고
    • 2,4-Diamino-5-formylpyrimidine and 2,4-diamino-5-hydroxymethylpyrimidine
    • Tieckelmann, H.; Guthrie, R.; Nairn, J. G. 2, 4-Diamino-5-formylpyrimidine and 2,4-diamino-5-hydroxymethylpyrimidine. J. Org. Chem. 1960, 25, 1257-9.
    • (1960) J. Org. Chem. , vol.25 , pp. 1257-1259
    • Tieckelmann, H.1    Guthrie, R.2    Nairn, J.G.3


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