메뉴 건너뛰기




Volumn 42, Issue 13, 1999, Pages 2447-2455

Pneumocystis carinii and Toxoplasma gondii dihydrofolate reductase inhibitors and antitumor agents: Synthesis and biological activities of 2,4- diamino-5-methyl-6-[(monosubstituted anilino)methyl]pyrido[2,3-d]pyrimidines

Author keywords

[No Author keywords available]

Indexed keywords

DIHYDROFOLATE REDUCTASE INHIBITOR;

EID: 0033168020     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm990079m     Document Type: Article
Times cited : (114)

References (36)
  • 2
    • 0029909611 scopus 로고    scopus 로고
    • Infection prophylaxis and antiretroviral therapy in patients with HIV infection and malignancy
    • Sparano, J. A.; Sara, C. Infection Prophylaxis and Antiretroviral Therapy in Patients with HIV Infection and Malignancy. Curr. Opin. Oncol. 1996, 8, 392-399.
    • (1996) Curr. Opin. Oncol. , vol.8 , pp. 392-399
    • Sparano, J.A.1    Sara, C.2
  • 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
    • 0025836272 scopus 로고
    • Pneumocystis carinii dihydrofolate reductase used to screen potenial antipneumocystis drugs
    • Broughton, M. C.; Queener, S. F. Pneumocystis carinii Dihydrofolate Reductase Used to Screen Potenial 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
  • 5
    • 0027177889 scopus 로고
    • Identification of highly potent and selective inhibitors of toxoplasma gondii dihydrofolate reductase
    • Ohio, L.-C.; Queener, S. F. Identification of Highly Potent and Selective Inhibitors of Toxoplasma gondii Dihydrofolate Reductase. Antimicrob. Agents Chemother. 1993, 37, 1914-1923.
    • (1993) Antimicrob. Agents Chemother. , vol.37 , pp. 1914-1923
    • Ohio, L.-C.1    Queener, S.F.2
  • 6
    • 0025746319 scopus 로고
    • Cost and benefit of secondary prophylaxis for Pneumocystis carinii pneumonia
    • Castellano, A. R.; Mettleman, 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    Mettleman, M.D.2
  • 7
    • 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
  • 8
    • 0023222307 scopus 로고
    • Activity of antifolates against Pneumocystis 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 Pneumocystis 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
  • 9
    • 0023155159 scopus 로고
    • In vitro and in vivo antitoxoplasma activity of the lipid-soluble antifolate trimetrexate
    • Allegra, C. J.; Kovacs, J. A.; Drake, 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    Chabner, B.A.4    Masur, H.P.5
  • 10
    • 0027177109 scopus 로고
    • Synergistic combination of Ro-11-8958 and other dihydrofolate reductase inhibitors with sulfamethoxazole and dapsone for therapy of experimental pneumocystosis
    • Walzer, P. D.; Foy, J.; Steele, P.; White, M. Synergistic Combination of Ro-11-8958 and Other Dihydrofolate Reductase Inhibitors with Sulfamethoxazole and Dapsone for Therapy of Experimental Pneumocystosis. Antimicrob. Agents Chemother. 1993, 37, 1436-1443.
    • (1993) Antimicrob. Agents Chemother. , vol.37 , pp. 1436-1443
    • Walzer, P.D.1    Foy, J.2    Steele, P.3    White, M.4
  • 11
    • 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.; Isrealski, 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    Isrealski, D.3
  • 12
    • 0023628797 scopus 로고
    • Activity of lipid-soluble inhibitors of dihydrofolate reductase against Pneumocystis carinii in culture and in a rat model of infection
    • Queener, S. F.; Bartlett, M. S.; Jay, M. A.; Durkin, M. M.; Smith, J. W. Activity of Lipid-Soluble Inhibitors 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
  • 14
    • 0028261664 scopus 로고
    • FDA approves trimetrexate as second line therapy of Pneumocystis carinii Pneumonia
    • News. FDA Approves Trimetrexate as Second line Therapy of Pneumocystis carinii Pneumonia. Am. J. Hosp. Pharm. 1994, 51, 591-592.
    • (1994) Am. J. Hosp. Pharm. , vol.51 , pp. 591-592
  • 16
    • 0027484260 scopus 로고
    • Synthesis of 5-Methyl-5-deaza nonclassical antifolates as inhibitors of dihydrofolate reductases and as potential antipneumocystis, antitoxoplasma, and antitumor agents
    • 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 Reductases 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
    • 0029042466 scopus 로고
    • 6-substituted 2,4-diamino-5-methylpyrido[2,3-d]pyrimidine8 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]pyrimidine8 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
  • 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 reductases
    • 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 Reductases. J. Med. Chem. 1997, 40, 479-485.
    • (1997) J. Med. Chem. , vol.40 , pp. 479-485
    • Gangjee, A.1    Vasudevan, A.2    Queener, S.F.3
  • 20
    • 0029875638 scopus 로고    scopus 로고
    • Lipophilic antifolates as agents against opportunistic infections. 1. Agents superior to trimetrexate and piritrexim against T. gondii and P. Carinii in in vitro evaluations
    • Piper, J. R.; Johnson, C. A.; Krauth, C. A.; Carter, R. L.; Hosmer, C. A.; Queener, S. F.; Borotz, S. E.; Pfefferkorn, E. R. Lipophilic Antifolates as Agents against Opportunistic Infections. 1. Agents Superior to Trimetrexate and Piritrexim against T. gondii and P. carinii in in Vitro Evaluations. J. Med. Chem. 1996, 39, 1271-1280.
    • (1996) J. Med. Chem. , vol.39 , pp. 1271-1280
    • Piper, J.R.1    Johnson, C.A.2    Krauth, C.A.3    Carter, R.L.4    Hosmer, C.A.5    Queener, S.F.6    Borotz, S.E.7    Pfefferkorn, E.R.8
  • 21
    • 0020492979 scopus 로고
    • Inhibition of dihydrofolate reductase: Effect of reduced nicotinamide adenine dinucleotide phosphate on the selectivity and affinity of diaminobenzylpyrimidines
    • Baccanari, D. B.; Saluge, S.; King, R. W. Inhibition of Dihydrofolate Reductase: Effect of Reduced Nicotinamide Adenine Dinucleotide Phosphate on the Selectivity and Affinity of Diaminobenzylpyrimidines. Biochemistry 1982, 21, 5068.
    • (1982) Biochemistry , vol.21 , pp. 5068
    • Baccanari, D.B.1    Saluge, S.2    King, R.W.3
  • 22
    • 0344725606 scopus 로고    scopus 로고
    • note
    • From the thesis submitted by Bindu Ramakrishnan to the Graduate School of Pharmaceutical Sciences, Duquesne University, in partial fulfillment of the requirements for the degree of Master of Science, April 1997.
  • 23
    • 0002854768 scopus 로고
    • Sirotnak, F. M., Burchall, J. J., Ensminger, W. D., Montgomery, J. A., Eds.; Academic Press: New York
    • Kisliuk, R. L. In Folate Antagonists as Therapeutic Agents; Sirotnak, F. M., Burchall, J. J., Ensminger, W. D., Montgomery, J. A., Eds.; Academic Press: New York, 1984; pp 1-68.
    • (1984) Folate Antagonists as Therapeutic Agents , pp. 1-68
    • Kisliuk, R.L.1
  • 24
    • 0022479337 scopus 로고
    • Synthesis and antifolate activity of 5-methyl-5-deaza analogues of aminopterin, methotrexate, folic acid and N10-methylfolic 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 Analogues of Aminopterin, Methotrexate, Folic Acid and N10-Methylfolic 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
  • 25
    • 33947089510 scopus 로고
    • New method for the methylation of amines
    • Borch, R. F.; Hassid, A. I. A New Method for the Methylation of Amines. J. Org. Chem. 1972, 37, 1673-1674.
    • (1972) J. Org. Chem. , vol.37 , pp. 1673-1674
    • Borch, R.F.1    Hassid, A.I.A.2
  • 26
    • 0344725605 scopus 로고    scopus 로고
    • note
    • a/w values were calculated using the LOGKOW Program, version 1.03, Syracuse Research Corp., Syracuse, NY 13210.
  • 28
    • 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
  • 29
    • 0021246884 scopus 로고
    • New micromethod to study the effect of antimicrobial agents on Toxoplasma gondii: Comparison of sulfadoxine and sulfadiazine individually and in combination with pyrimethamine and study of clindamycin, metronidazole and cyclosporin A Antimicrob
    • Mack, D. G.; McLeod, R. New Micromethod to Study the Effect of Antimicrobial Agents on Toxoplasma gondii: Comparison of Sulfadoxine and Sulfadiazine Individually and in Combination with Pyrimethamine and Study of Clindamycin, Metronidazole and Cyclosporin A Antimicrob. Agents Chemother. 1984, 26, 26-30.
    • (1984) Agents Chemother. , vol.26 , pp. 26-30
    • Mack, D.G.1    McLeod, R.2
  • 33
    • 0027491678 scopus 로고
    • 8-aminoquinolines effective against Pneumocystis carinii in vitro and in vivo
    • Queener, S. F.; Bartlett, M. S.; Nasr, M.; Smith, J. W. 8-Aminoquinolines Effective Against Pneumocystis carinii in vitro and in vivo. Antimicrob. Agents Chemother. 1993, 37, 2166-2172.
    • (1993) Antimicrob. Agents Chemother. , vol.37 , pp. 2166-2172
    • Queener, S.F.1    Bartlett, M.S.2    Nasr, M.3    Smith, J.W.4
  • 34
    • 0026647832 scopus 로고
    • Efficacy of intermittent dosage of 8-aminoquinolines for therapy or prophylaxis of Pneumocystis carinii Pneumonia in rats
    • Queener, S. F.; Dean, R. A.; Bartlett, M. S.; Milhous, W. K.; Berman, J. D.; Ellis, W. Y.; Smith, J. W. Efficacy of Intermittent Dosage of 8-Aminoquinolines for Therapy or Prophylaxis of Pneumocystis carinii Pneumonia in Rats. J. Infect. Dis. 1992, 165, 764-768.
    • (1992) J. Infect. Dis. , vol.165 , pp. 764-768
    • Queener, S.F.1    Dean, R.A.2    Bartlett, M.S.3    Milhous, W.K.4    Berman, J.D.5    Ellis, W.Y.6    Smith, J.W.7
  • 35
    • 0028291789 scopus 로고
    • Primary structure and expression of the dihydropteroate synthetase gene of Plasmodium falciparum
    • Triglia, T.; Cowman, A. F. Primary Structure and Expression of the Dihydropteroate Synthetase Gene of Plasmodium falciparum. Proc. Natl. Acad. Sci. U.S.A 1994, 91, 7149-7153.
    • (1994) Proc. Natl. Acad. Sci. U.S.A , vol.91 , pp. 7149-7153
    • Triglia, T.1    Cowman, A.F.2
  • 36
    • 0345155946 scopus 로고    scopus 로고
    • note
    • We thank the Developmental Therapeutics Program of the NCI for performing the in vitro anticancer evaluation.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.