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Volumn 39, Issue 9, 1996, Pages 1836-1845

Nonclassical 2,4-diamino-8-deazafolate analogues as inhibitors of dihydrofolate reductases from rat liver, Pneumocystis carinii, and Toxoplasma gondii

Author keywords

[No Author keywords available]

Indexed keywords

2,4 DIAMINO 6 [(2 CHLORO N METHYLANILINO)METHYL]PYRIDO[3,2 D]PYRIMIDINE; 2,4 DIAMINO 6 [(2,4,6 TRICHLOROANILINO)METHYL]PYRIDO[3,2 D]PYRIMIDINE; 2,4 DIAMINO 6 [(3,4,5 TRIMETHOXYANILINO)METHYL]PYRIDO[3,2 D]PYRIMIDINE; DIHYDROFOLATE REDUCTASE INHIBITOR; PYRIMIDINE DERIVATIVE; TRIMETREXATE; UNCLASSIFIED DRUG;

EID: 0029881975     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm950918e     Document Type: Article
Times cited : (31)

References (38)
  • 1
    • 0025746319 scopus 로고
    • Cost and Benefit of Secondary Prophylaxis for Pneumocystis carinii Pneumonia
    • Castellano, A. R.; Nettleman, M. D. Cost and Benefit of Secondary Prophylaxis for Pneumocystis carinii Pneumonia. J. Am. Med. Assoc. 1991, 266, 820-824.
    • (1991) J. Am. Med. Assoc. , vol.266 , pp. 820-824
    • Castellano, A.R.1    Nettleman, M.D.2
  • 2
    • 0027171549 scopus 로고
    • Opportunistic/Nosocomial Infections. Treatment and Developmental Therapeutics. Toxoplasmosis
    • St. Georgiev, V. Opportunistic/Nosocomial Infections. Treatment and Developmental Therapeutics. Toxoplasmosis. Med. Res. Rev. 1993, 13, 529-568.
    • (1993) Med. Res. Rev. , vol.13 , pp. 529-568
    • St. Georgiev, V.1
  • 3
    • 0025847523 scopus 로고
    • Pneumocystis carinii. An Opportunist in Immunocompromised Patients
    • Bartlett, M. S.; Smith, J. W. Pneumocystis carinii. An Opportunist in Immunocompromised Patients. Clin. Microbiol. Rev. 1991, 4, 137-149.
    • (1991) Clin. Microbiol. Rev. , vol.4 , pp. 137-149
    • Bartlett, M.S.1    Smith, J.W.2
  • 4
    • 0026558453 scopus 로고
    • New Developments in the Treatment of Pneumocystis carinii Pneumonia
    • Sattler, F. R.; Feinberg, J. New Developments in the Treatment of Pneumocystis carinii Pneumonia. Chest 1992, 101, 451-457.
    • (1992) Chest , vol.101 , pp. 451-457
    • Sattler, F.R.1    Feinberg, J.2
  • 5
    • 0025359375 scopus 로고
    • Aerosolized Pentadiamine: Effect on Diagnosis and Presentation of Pneumocystis carinii Pneumonia
    • Jules-Elysee, K. M.; Strover, D. E.; Zaman, M. B.; Bernard, E. M.; White, D. A. Aerosolized Pentadiamine: Effect on Diagnosis and Presentation of Pneumocystis carinii Pneumonia. Ann. Intern. Med. 1990, 112, 750-757.
    • (1990) Ann. Intern. Med. , vol.112 , pp. 750-757
    • Jules-Elysee, K.M.1    Strover, D.E.2    Zaman, M.B.3    Bernard, E.M.4    White, D.A.5
  • 6
    • 0027126413 scopus 로고
    • Drug Therapy. Prevention and Treatment of Pneumocystis Pneumonia
    • Masur, H. Drug Therapy. Prevention and Treatment of Pneumocystis Pneumonia. N. Engl J. Med. 1992, 327, 1853-1860.
    • (1992) N. Engl J. Med. , vol.327 , pp. 1853-1860
    • Masur, H.1
  • 7
    • 0026515452 scopus 로고
    • Treatment of Toxoplasmic Encephalitis in Patients with AIDS: A Randomized Trial Comparing Pyrimethamine Plus Clindamycin to Pyrimethamine Plus Sulfadiazine
    • Dannemann, B.; McCutchan, J. A.; Israelski, D. Treatment of Toxoplasmic Encephalitis in Patients with AIDS: A Randomized Trial Comparing Pyrimethamine Plus Clindamycin to Pyrimethamine Plus Sulfadiazine. Ann. Intern. Med. 1992, 116, 33-43.
    • (1992) Ann. Intern. Med. , vol.116 , pp. 33-43
    • Dannemann, B.1    McCutchan, J.A.2    Israelski, D.3
  • 8
    • 0027278550 scopus 로고
    • Pharmacokinetic Optimization in the Treatment of Pneumocystis carinii Pneumonia
    • Vohringer, H. F.; Arasteh, K. Pharmacokinetic Optimization in the Treatment of Pneumocystis carinii Pneumonia. Pharmacokinetics 1993, 24, 388.
    • (1993) Pharmacokinetics , vol.24 , pp. 388
    • Vohringer, H.F.1    Arasteh, K.2
  • 9
    • 0023222307 scopus 로고
    • Activity of Antifolates Against Pneumocustis carinii Dihydrofolate Reductase and Identification of a Potent New Agent
    • Allegra, C. J.; Kovacs, J. A.; Drake, J. C.; Swan, J. C.; Chabner, B. A.; Masur, H. Activity of Antifolates Against Pneumocustis carinii Dihydrofolate Reductase and Identification of a Potent New Agent. J. Exp. Med. 1987, 165, 926-931.
    • (1987) J. Exp. Med. , vol.165 , pp. 926-931
    • Allegra, C.J.1    Kovacs, J.A.2    Drake, J.C.3    Swan, J.C.4    Chabner, B.A.5    Masur, H.6
  • 10
    • 0023155159 scopus 로고
    • Potent in Vitro and in Vivo Antitoxoplasma Activity of the Lipid-Soluble Antifolate Trimetrexate
    • Allegra, C J.; Kovacs, J. A.; Drake, J. C.; Swan, J. C.; Chabner, B. A.; Masur, H. Potent In Vitro and In Vivo Antitoxoplasma Activity of the Lipid-Soluble Antifolate Trimetrexate. J. Clin. Invest. 1987, 79, 478-482.
    • (1987) J. Clin. Invest. , vol.79 , pp. 478-482
    • Allegra, C.J.1    Kovacs, J.A.2    Drake, J.C.3    Swan, J.C.4    Chabner, B.A.5    Masur, H.6
  • 12
    • 0023628797 scopus 로고
    • Activity of Lipid-Soluble Inhibitiors of Dihydrofolate Reductase Against Pneumocystis carinii in Culture and in a Rat Model of Infection
    • (a) Queener, S. F.; Bartlett, M. S.; Jay, M. A.; Durkin, M. M.; Smith, J. W. Activity of Lipid-Soluble Inhibitiors of Dihydrofolate Reductase Against Pneumocystis carinii in Culture and in a Rat Model of Infection. Antimicrob. Agents Chemother. 1987, 31, 1323-1327.
    • (1987) Antimicrob. Agents Chemother. , vol.31 , pp. 1323-1327
    • Queener, S.F.1    Bartlett, M.S.2    Jay, M.A.3    Durkin, M.M.4    Smith, J.W.5
  • 13
    • 15844382936 scopus 로고
    • Identification of Potent Innhibitors of Toxoplasma gondii Dihydrofolate Reductase
    • (b) Queener, S. F. Identification of Potent Innhibitors of Toxoplasma gondii Dihydrofolate Reductase. Antimicrob. Agents Chemother. 1993, 35, 1348-1355.
    • (1993) Antimicrob. Agents Chemother. , vol.35 , pp. 1348-1355
    • Queener, S.F.1
  • 16
    • 0027484260 scopus 로고
    • Synthesis of 5-Methyl-5-Deaza Nonclassical Antifolates as Inhibitors of Dihydrofolate Reductase and as Potential Antipneumocystis, Antitoxoplasma and Antitumor Agents
    • (a) Gangjee, A.; Shi, J.; Queener, S. F.; Barrows, L. R.; Kisliuk, R. L. Synthesis of 5-Methyl-5-Deaza Nonclassical Antifolates as Inhibitors of Dihydrofolate Reductase and as Potential Antipneumocystis, Antitoxoplasma and Antitumor Agents. J. Med. Chem. 1993, 36, 3437-3443.
    • (1993) J. Med. Chem. , vol.36 , pp. 3437-3443
    • Gangjee, A.1    Shi, J.2    Queener, S.F.3    Barrows, L.R.4    Kisliuk, R.L.5
  • 17
    • 0027364787 scopus 로고
    • Synthesis and Biological Activities of Tricyclic Conformationally Restricted Analogues of Lipophilic Pyrido[2,3-d]pyrimidines
    • (b) Gangjee, A.; Mavandadi, F.; Lin, F. T. Synthesis and Biological Activities of Tricyclic Conformationally Restricted Analogues of Lipophilic Pyrido[2,3-d]pyrimidines. Adv. Exp. Med. Biol. 1993, 338, 441-444.
    • (1993) Adv. Exp. Med. Biol. , vol.338 , pp. 441-444
    • Gangjee, A.1    Mavandadi, F.2    Lin, F.T.3
  • 18
    • 0028281539 scopus 로고
    • Classical and Nonclassical Furo[2,3-d]pyrimidines as Novel Antifolates: Synthesis and Biological Activities
    • (c) Gangjee, A.; Devraj, R.; McGuire, J. J.; Kisliuk, R. L.; Queener, S. F.; Barrows, L. R. Classical and Nonclassical Furo[2,3-d]pyrimidines as Novel Antifolates: Synthesis and Biological Activities. J. Med. Chem. 1994, 37, 1169-1176.
    • (1994) J. Med. Chem. , vol.37 , pp. 1169-1176
    • Gangjee, A.1    Devraj, R.2    McGuire, J.J.3    Kisliuk, R.L.4    Queener, S.F.5    Barrows, L.R.6
  • 19
    • 0029072232 scopus 로고
    • Novel 2,4-Diamino-5-Substituted Pyrrolo[2,3-d]pyrimidmes as Classical and Nonclassical Inhibitors of Dihydrofolate Reductases
    • (d) Gangjee, A.; Mavandadi, F.; Queener, S F.; McGuire, J. J. Novel 2,4-Diamino-5-Substituted Pyrrolo[2,3-d]pyrimidmes as Classical and Nonclassical Inhibitors of Dihydrofolate Reductases. J. Med. Chem. 1995, 38, 2158-2165.
    • (1995) J. Med. Chem. , vol.38 , pp. 2158-2165
    • Gangjee, A.1    Mavandadi, F.2    Queener, S.F.3    McGuire, J.J.4
  • 20
    • 0024365067 scopus 로고
    • Tricyclic 2,4-Diaminopyrimidmes with Broad Antifolate Activity and the Ability to Inhibit Pneumocystis carinii Growth in Cultured Human Fibroblasts in the Presence of Leucovorin
    • (a) Rosowsky, A.; Freisheim, J. H.; Hynes, J. B.; Queener, S. F.; Bartlett, M.; Smith, J. W.; Lazarus, H.; Modest, E. J. Tricyclic 2,4-Diaminopyrimidmes with Broad Antifolate Activity and the Ability to Inhibit Pneumocystis carinii Growth in Cultured Human Fibroblasts in the Presence of Leucovorin. Biochem. Pharmacol. 1989, 38, 2677-2684.
    • (1989) Biochem. Pharmacol. , vol.38 , pp. 2677-2684
    • Rosowsky, A.1    Freisheim, J.H.2    Hynes, J.B.3    Queener, S.F.4    Bartlett, M.5    Smith, J.W.6    Lazarus, H.7    Modest, E.J.8
  • 21
    • 0028960581 scopus 로고
    • 2,4-Diamino-5-Substituted-Quinazolines as Inhibitors of a Human Dihydrofolate Reductase with a Site-Directed Mutation at Position 22 and of the Dihydrofolate Reductases from Pneumocystis carinii and Toxoplasma gondii
    • (b) Rosowsky, A.; Mota, C. E.; Queener, S. F.; Waltham, M.; Ercikan-Abali, E.; Bertino, J. R. 2,4-Diamino-5-Substituted-Quinazolines as Inhibitors of a Human Dihydrofolate Reductase with a Site-Directed Mutation at Position 22 and of the Dihydrofolate Reductases from Pneumocystis carinii and Toxoplasma gondii. J. Med. Chem. 1995, 38, 745-752.
    • (1995) J. Med. Chem. , vol.38 , pp. 745-752
    • Rosowsky, A.1    Mota, C.E.2    Queener, S.F.3    Waltham, M.4    Ercikan-Abali, E.5    Bertino, J.R.6
  • 22
    • 0027375375 scopus 로고
    • 2,4-Diaminothieno[2,3-d]pyrimidine Analogues of Trimetrexate and Piritrexim as Potential Inhibitors of Pneumocystis carinii and Toxoplasma gondii Dihydrofolate Reductase
    • (c) Rosowsky, A.; Mota, C. E.; Wright, J. E.; Freisheim, J. H.; Heusner, J. J.; McCormack, J. J.; Queener, S. F. 2,4-Diaminothieno[2,3-d]pyrimidine Analogues of Trimetrexate and Piritrexim as Potential Inhibitors of Pneumocystis carinii and Toxoplasma gondii Dihydrofolate Reductase. J. Med. Chem. 1993, 36, 3103-3112.
    • (1993) J. Med. Chem. , vol.36 , pp. 3103-3112
    • Rosowsky, A.1    Mota, C.E.2    Wright, J.E.3    Freisheim, J.H.4    Heusner, J.J.5    McCormack, J.J.6    Queener, S.F.7
  • 24
    • 0025836272 scopus 로고
    • Pneumocystis carinii Dihydrofolate Reductase Used to Screen Potential Antipneumocystis Drugs
    • Broughton, M. C.; Queener, S. F. Pneumocystis carinii Dihydrofolate Reductase Used to Screen Potential Antipneumocystis Drugs. Antimicrob. Agents Chemother. 1991, 35, 1348-1355.
    • (1991) Antimicrob. Agents Chemother. , vol.35 , pp. 1348-1355
    • Broughton, M.C.1    Queener, S.F.2
  • 25
    • 15844415802 scopus 로고    scopus 로고
    • personal communication
    • Sherry F. Queener, personal communication.
    • Queener, S.F.1
  • 26
    • 0027177889 scopus 로고
    • Identification of Highly Potent and Selective Inhibitors of Toxoplasma gondii Dihydrofolate Reductase
    • Chio, L.-C.; Queener, S. F. Identification of Highly Potent and Selective Inhibitors of Toxoplasma gondii Dihydrofolate Reductase. Antimicrob. Agents Chemother. 1993, 337, 1914-1923.
    • (1993) Antimicrob. Agents Chemother. , vol.337 , pp. 1914-1923
    • Chio, L.-C.1    Queener, S.F.2
  • 27
    • 0029042466 scopus 로고
    • 6-Substituted 2,4-Diamino-5-methylpyrido[2,3-d]pyrimidines as Inhibitors of Dihydrofolate Reductases from Pneumocystis carinii and Toxoplasma gondii and as Antitumor Agents
    • Gangjee, A.; Vasudevan, A.; Queener, S. F.; Kisliuk, R. L. 6-Substituted 2,4-Diamino-5-methylpyrido[2,3-d]pyrimidines as Inhibitors of Dihydrofolate Reductases from Pneumocystis carinii and Toxoplasma gondii and as Antitumor Agents. J. Med. Chem. 1995, 38, 1778-1785.
    • (1995) J. Med. Chem. , vol.38 , pp. 1778-1785
    • Gangjee, A.1    Vasudevan, A.2    Queener, S.F.3    Kisliuk, R.L.4
  • 28
    • 0015975685 scopus 로고
    • Antimicrobial Activity of 8-Deaza Folie Acid
    • DeGraw, J. I.; Kisliuk, R. L.; Gaumont, Y. Antimicrobial Activity of 8-Deaza Folie Acid. J. Med. Chem. 1974, 17, 470-471.
    • (1974) J. Med. Chem. , vol.17 , pp. 470-471
    • DeGraw, J.I.1    Kisliuk, R.L.2    Gaumont, Y.3
  • 29
    • 0019439183 scopus 로고
    • Pyridopyrimidines. 12. Synthesis of 8-Deaza Analogues of Aminopterin and Folic Acid
    • (a) Srinivasan, A.; Broom, A. D. Pyridopyrimidines. 12. Synthesis of 8-Deaza Analogues of Aminopterin and Folic Acid. J. Org. Chem. 1981, 46, 1777-1781.
    • (1981) J. Org. Chem. , vol.46 , pp. 1777-1781
    • Srinivasan, A.1    Broom, A.D.2
  • 30
    • 0040927120 scopus 로고
    • Pyridopyrimidines. 10. Nucleophuic Substitution in the Pyrido[3,2-d]pyrimidine Series
    • (b) Srinivasan, A.; Broom, A. D. Pyridopyrimidines. 10. Nucleophuic Substitution in the Pyrido[3,2-d]pyrimidine Series. J. Org. Chem. 1979, 44, 435-440.
    • (1979) J. Org. Chem. , vol.44 , pp. 435-440
    • Srinivasan, A.1    Broom, A.D.2
  • 31
    • 0023852531 scopus 로고
    • Probing the Thymidylate Synthase Active Site with Bisubstrate Analog Inhibitors
    • (c) Bayomi, S. M. M.; Brixner, D. I.; Eisa, H.; Broom, A. D. Probing the Thymidylate Synthase Active Site with Bisubstrate Analog Inhibitors. Nucleosides Nucleotides 1988, 7, 103-115.
    • (1988) Nucleosides Nucleotides , vol.7 , pp. 103-115
    • Bayomi, S.M.M.1    Brixner, D.I.2    Eisa, H.3    Broom, A.D.4
  • 32
    • 15844422483 scopus 로고
    • Polyazanaphthalenes. Part VII. Some Derivatives of Quinazoline and 1,3,5-Triazanaphthalene
    • Oakes, V.; Rydon, H. N.; Undheim, K. Polyazanaphthalenes. Part VII. Some Derivatives of Quinazoline and 1,3,5-Triazanaphthalene. J. Chem. Soc. 1962, 4678-4683.
    • (1962) J. Chem. Soc. , pp. 4678-4683
    • Oakes, V.1    Rydon, H.N.2    Undheim, K.3
  • 33
    • 0021714938 scopus 로고
    • A Potent Multisubstrate Analogue Inhibitor of Human Thymidylate Synthetase
    • Srinivasan, A.; Amarnath, V.; Broom, A. D.; Zou, F. C.; Chen, Y.-C. A Potent Multisubstrate Analogue Inhibitor of Human Thymidylate Synthetase. J. Med. Chem. 1984, 27, 1710-1717.
    • (1984) J. Med. Chem. , vol.27 , pp. 1710-1717
    • Srinivasan, A.1    Amarnath, V.2    Broom, A.D.3    Zou, F.C.4    Chen, Y.-C.5
  • 34
    • 37049128880 scopus 로고
    • Synthesis of Pyrido[3,2-d]pyrimidines from 5-Aminopyrimidines
    • Irwin, W. J.; Wibberley, D. J. Synthesis of Pyrido[3,2-d]pyrimidines from 5-Aminopyrimidines. J. Chem. Soc. C 1967, 1745-1750.
    • (1967) J. Chem. Soc. C , pp. 1745-1750
    • Irwin, W.J.1    Wibberley, D.J.2
  • 35
    • 0025365265 scopus 로고
    • Potent Inhibition of Thymidylate Synthase by Two Series of Nonclassical Quinazolines
    • McNamara, D. J.; Berman, E. M ; Fry, D. W.; Werbel, L. M. Potent Inhibition of Thymidylate Synthase by Two Series of Nonclassical Quinazolines. J. Med. Chem. 1990, 33, 2045-2051.
    • (1990) J. Med. Chem. , vol.33 , pp. 2045-2051
    • McNamara, D.J.1    Berman, E.M.2    Fry, D.W.3    Werbel, L.M.4
  • 36
    • 0000831309 scopus 로고
    • The Reduction of Aryl Trifluoromethyl Ketones by Sodium Borohydride. The Hydride Transfer Process
    • Stewart, R.; Teo, K. C. The Reduction of Aryl Trifluoromethyl Ketones by Sodium Borohydride. The Hydride Transfer Process. Can. J. Chem. 1980, 58, 2491-2496.
    • (1980) Can. J. Chem. , vol.58 , pp. 2491-2496
    • Stewart, R.1    Teo, K.C.2
  • 37
    • 0001645508 scopus 로고
    • The Electronic Properties of Fluoroalkyl Groups. Fluorine p-Interaction
    • Sheppard, W. A. The Electronic Properties of Fluoroalkyl Groups. Fluorine p-Interaction. J. Am. Chem. Soc. 1965, 87, 2410-2420.
    • (1965) J. Am. Chem. Soc. , vol.87 , pp. 2410-2420
    • Sheppard, W.A.1
  • 38
    • 0029046841 scopus 로고
    • 2,4-Diaminopyrido[3,2-d]pyrimidine Inhibitors of Dihydrofolate Reductase from Pneumocystis carinii and Toxoplasma gondii
    • Rosowsky, A.; Forsch, R. A.; Queener, S. F. 2,4-Diaminopyrido[3,2-d]pyrimidine Inhibitors of Dihydrofolate Reductase from Pneumocystis carinii and Toxoplasma gondii. J. Med. Chem. 1995, 38, 2615-2620.
    • (1995) J. Med. Chem. , vol.38 , pp. 2615-2620
    • Rosowsky, A.1    Forsch, R.A.2    Queener, S.F.3


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