메뉴 건너뛰기




Volumn 50, Issue 14, 2007, Pages 3283-3289

Novel boron-containing, nonclassical antifolates: Synthesis and preliminary biological and structural evaluation

Author keywords

[No Author keywords available]

Indexed keywords

2,4 DIAMINO 6 METHYLPYRIDINE; 5 (1,2 CLOSO DICARBADODECABORAN 1 YL)METHYLPYRIMIDINE; 5 (7,8 NIDO DICARBAUNDECARBORAN 7 YL)METHYLPYRIMIDINE; BORON DERIVATIVE; CARBORANE DERIVATIVE; DIHYDROFOLATE REDUCTASE; DIHYDRONICONATINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; ETHAMBUTOL; FOLIC ACID ANTAGONIST; METHOTREXATE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; TRIMETHOPRIM; UNCLASSIFIED DRUG;

EID: 34447520293     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0701977     Document Type: Article
Times cited : (73)

References (39)
  • 1
    • 0034991780 scopus 로고    scopus 로고
    • Update on antifolate drugs targets
    • Costi, M. P.; Ferrari, S. Update on antifolate drugs targets. Curr. Drug Targets 2001, 2, 135-166.
    • (2001) Curr. Drug Targets , vol.2 , pp. 135-166
    • Costi, M.P.1    Ferrari, S.2
  • 2
    • 0029129154 scopus 로고    scopus 로고
    • Takimoto, C. H.; Allegra, C. J. New antifolates in clinical development. Oncology 1995, 9, 649-656, 659 DISC 660, 662, 665.
    • Takimoto, C. H.; Allegra, C. J. New antifolates in clinical development. Oncology 1995, 9, 649-656, 659 DISC 660, 662, 665.
  • 3
    • 0035463331 scopus 로고    scopus 로고
    • Antifolate resistance and its circumvention by new analogues
    • Takemura, Y.; Kobayashi, H.; Miyachi, H. Antifolate resistance and its circumvention by new analogues. Hum. Cell 2001, 14, 185-202.
    • (2001) Hum. Cell , vol.14 , pp. 185-202
    • Takemura, Y.1    Kobayashi, H.2    Miyachi, H.3
  • 4
    • 0036261415 scopus 로고    scopus 로고
    • Future directions in the development of pemetrexed
    • Calvert, H.; Bunn, P. A., Jr. Future directions in the development of pemetrexed. Semin. Oncol. 2002, 29, 54-61.
    • (2002) Semin. Oncol , vol.29 , pp. 54-61
    • Calvert, H.1    Bunn Jr., P.A.2
  • 5
    • 0029038432 scopus 로고    scopus 로고
    • Periti, P. Brodimoprim, a new bacterial dihydrofolate reductase inhibitor: A minireview. J. Chemother. 1995, 7, 221-223.
    • Periti, P. Brodimoprim, a new bacterial dihydrofolate reductase inhibitor: A minireview. J. Chemother. 1995, 7, 221-223.
  • 6
    • 0036358879 scopus 로고    scopus 로고
    • Resistance to antifolates in Plasmodium falciparum, the causative agent of tropical malaria
    • Warhurst, D. C. Resistance to antifolates in Plasmodium falciparum, the causative agent of tropical malaria. Sci. Prog. 2002, 85, 89-111.
    • (2002) Sci. Prog , vol.85 , pp. 89-111
    • Warhurst, D.C.1
  • 7
    • 0035051117 scopus 로고    scopus 로고
    • Methotrexate therapy in systemic lupus erythematosus
    • Sato, E. I. Methotrexate therapy in systemic lupus erythematosus. Lupus 2001, 10, 162-164.
    • (2001) Lupus , vol.10 , pp. 162-164
    • Sato, E.I.1
  • 9
    • 0035310803 scopus 로고    scopus 로고
    • Reynolds, R. C.; Johnson, C. A.; Piper, J. R.; Sirotnak, F. M. Synthesis and antifolate evaluation of the aminopterin analogue with a bicyclo[2.2.2]octane ring in place of the benzene ring. Eur. J. Med. Chem. 2001, 36, 237-242.
    • Reynolds, R. C.; Johnson, C. A.; Piper, J. R.; Sirotnak, F. M. Synthesis and antifolate evaluation of the aminopterin analogue with a bicyclo[2.2.2]octane ring in place of the benzene ring. Eur. J. Med. Chem. 2001, 36, 237-242.
  • 10
    • 0004150764 scopus 로고
    • Academic Press: New York
    • Grimes, R. N. Carboranes; Academic Press: New York, 1970.
    • (1970) Carboranes
    • Grimes, R.N.1
  • 11
    • 34447548413 scopus 로고    scopus 로고
    • Hitchings, G. H.; Baccanari, D. P. Design and synthesis of folate antagonists as antimicrobial agents. In Folate Antagonists as Therapeutic Agents. I, Biochemistry, Molecular Actions and Synthetic Design; Sirotnak, F. M., Burchall, J. J., Ensminger, W. B., Montgomery, J. A., Eds.; Academic Press: New York, 1984; pp 151-172.
    • Hitchings, G. H.; Baccanari, D. P. Design and synthesis of folate antagonists as antimicrobial agents. In Folate Antagonists as Therapeutic Agents. Volume I, Biochemistry, Molecular Actions and Synthetic Design; Sirotnak, F. M., Burchall, J. J., Ensminger, W. B., Montgomery, J. A., Eds.; Academic Press: New York, 1984; pp 151-172.
  • 12
    • 0032979995 scopus 로고    scopus 로고
    • Boron neutron capture therapy of brain tumors: An emerging therapeutic modality
    • discussion 450-451, review
    • Barth, R. F.; Soloway, A. H.; Goodman, J. H.; Gahbauer, R. A.; Gupta, N.; Blue, T. E.; Yang, W.; Tjarks, W. Boron neutron capture therapy of brain tumors: An emerging therapeutic modality. Neurosurgery 1999, 44, 433-451; discussion 450-451, review.
    • (1999) Neurosurgery , vol.44 , pp. 433-451
    • Barth, R.F.1    Soloway, A.H.2    Goodman, J.H.3    Gahbauer, R.A.4    Gupta, N.5    Blue, T.E.6    Yang, W.7    Tjarks, W.8
  • 13
    • 0031978603 scopus 로고    scopus 로고
    • New horizons for therapy based on the boron neutron capture reaction
    • Hawthorne, M. F. New horizons for therapy based on the boron neutron capture reaction. Mol. Med. Today 1998, 4, 174-181.
    • (1998) Mol. Med. Today , vol.4 , pp. 174-181
    • Hawthorne, M.F.1
  • 16
    • 0025765516 scopus 로고
    • 2,4-Dichloro-5-(1-o- carboranylmethyl)-6-methylpyrimidine: A potential synthon for 5-(1-o-carboranylmethyl)pyrimidines
    • Reynolds, R. C.; Trask, T. W.; Sedwick, W. D. 2,4-Dichloro-5-(1-o- carboranylmethyl)-6-methylpyrimidine: A potential synthon for 5-(1-o-carboranylmethyl)pyrimidines. J. Org. Chem. 1991, 56, 2391-2395.
    • (1991) J. Org. Chem , vol.56 , pp. 2391-2395
    • Reynolds, R.C.1    Trask, T.W.2    Sedwick, W.D.3
  • 17
    • 33947483935 scopus 로고
    • Dicarbaundecaborane(13) and derivatives
    • Wiesboeck, R. A.; Hawthorne, M. F. Dicarbaundecaborane(13) and derivatives. J. Am. Chem. Soc. 1964, 86, 1642-1643.
    • (1964) J. Am. Chem. Soc , vol.86 , pp. 1642-1643
    • Wiesboeck, R.A.1    Hawthorne, M.F.2
  • 19
    • 0031465609 scopus 로고    scopus 로고
    • Synthesis and in vitro evaluation of 5-closo- and 5-nido-orthocarboranyluridines as boron carriers
    • Imamura, K.-i.; Yamamoto, Y. Synthesis and in vitro evaluation of 5-closo- and 5-nido-orthocarboranyluridines as boron carriers. Bull. Chem. Soc. Jpn. 1997, 70, 3103-3110.
    • (1997) Bull. Chem. Soc. Jpn , vol.70 , pp. 3103-3110
    • Imamura, K.-I.1    Yamamoto, Y.2
  • 20
    • 0036311129 scopus 로고    scopus 로고
    • Atomic structures of human dihydrofolate reductase complexed with NADPH and two lipophilic antifolates at 1.09 Å and 1.05 Å resolution
    • Klon, A. E.; Heroux, A.; Ross, L. J.; Pathak, V.; Johnson, C. A.; Piper, J. R.; Borhani, D. W. Atomic structures of human dihydrofolate reductase complexed with NADPH and two lipophilic antifolates at 1.09 Å and 1.05 Å resolution. J. Mol. Biol. 2002, 320, 677-693.
    • (2002) J. Mol. Biol , vol.320 , pp. 677-693
    • Klon, A.E.1    Heroux, A.2    Ross, L.J.3    Pathak, V.4    Johnson, C.A.5    Piper, J.R.6    Borhani, D.W.7
  • 21
    • 0001514067 scopus 로고
    • Efficient and accurate calculation of anion proton affinities
    • Chandrasekhar, J.; Andrade, J. G.; Schleyer, P. v. R. Efficient and accurate calculation of anion proton affinities. J. Am. Chem. Soc. 1981, 103, 5609-5612.
    • (1981) J. Am. Chem. Soc , vol.103 , pp. 5609-5612
    • Chandrasekhar, J.1    Andrade, J.G.2    Schleyer, P.V.R.3
  • 22
    • 84986468498 scopus 로고
    • Stabilization of methyl anions by first-row substituents. The superiority of diffuse function-augmented basis sets for anion calculations
    • Spitznagel, G. W.; Clark, T.; Chandrasekhar, J.; Schleyer, P. v. R. Stabilization of methyl anions by first-row substituents. The superiority of diffuse function-augmented basis sets for anion calculations. J. Comput. Chem. 1982, 3, 363-371.
    • (1982) J. Comput. Chem , vol.3 , pp. 363-371
    • Spitznagel, G.W.1    Clark, T.2    Chandrasekhar, J.3    Schleyer, P.V.R.4
  • 23
    • 84986468715 scopus 로고
    • Efficient diffuse function-augmented basis sets for anion calculations. III. The 3-21 + G basis set for first-row elements, lithium to fluorine
    • Clark, T.; Chandrasekhar, J.; Spitznagel, G. W.; Schleyer, P. v. R. Efficient diffuse function-augmented basis sets for anion calculations. III. The 3-21 + G basis set for first-row elements, lithium to fluorine. J. Comput. Chem. 1983, 4, 294-301.
    • (1983) J. Comput. Chem , vol.4 , pp. 294-301
    • Clark, T.1    Chandrasekhar, J.2    Spitznagel, G.W.3    Schleyer, P.V.R.4
  • 26
    • 0018890752 scopus 로고
    • 2,4-Diamino-5- benzylpyrimidines as antibacterial agents. 4. 6-Substituted trimethoprim derivatives from phenolic Mannich intermediates. Application to the synthesis of trimethoprim and 3,5-dialkylbenzyl analogues
    • Roth, B.; Aig, E.; Lane, K.; Rauckman, B. S. 2,4-Diamino-5- benzylpyrimidines as antibacterial agents. 4. 6-Substituted trimethoprim derivatives from phenolic Mannich intermediates. Application to the synthesis of trimethoprim and 3,5-dialkylbenzyl analogues. J. Med. Chem. 1980, 23, 535-541.
    • (1980) J. Med. Chem , vol.23 , pp. 535-541
    • Roth, B.1    Aig, E.2    Lane, K.3    Rauckman, B.S.4
  • 27
    • 34447569027 scopus 로고    scopus 로고
    • Werbel, L. M. Design and synthesis of lipophilic antifols as anticancer agents. In Folate Antagonists as Therapeutic Agents. I, Biochemistry, Molecular Actions and Synthetic Design; Sirotnak, F. M., Burchall, J. J., Ensminger, W. B., Montgomery, J. A., Eds.; Academic Press: New York, 1984; pp 261-287.
    • Werbel, L. M. Design and synthesis of lipophilic antifols as anticancer agents. In Folate Antagonists as Therapeutic Agents. Volume I, Biochemistry, Molecular Actions and Synthetic Design; Sirotnak, F. M., Burchall, J. J., Ensminger, W. B., Montgomery, J. A., Eds.; Academic Press: New York, 1984; pp 261-287.
  • 28
    • 0027743035 scopus 로고
    • Basis of selectivity of antibacterial diaminopyrimidines
    • Baccanari, D. P.; Kuyper, L. F. Basis of selectivity of antibacterial diaminopyrimidines. J. Chemother. 1993, 5, 393-399.
    • (1993) J. Chemother , vol.5 , pp. 393-399
    • Baccanari, D.P.1    Kuyper, L.F.2
  • 29
    • 0027737508 scopus 로고
    • Molecular aspects and mechanism of action of dihydrofolate reductase inhibitors
    • Hartman, P. G. Molecular aspects and mechanism of action of dihydrofolate reductase inhibitors. J. Chemother. 1993, 5, 369-376.
    • (1993) J. Chemother , vol.5 , pp. 369-376
    • Hartman, P.G.1
  • 30
    • 0017672047 scopus 로고    scopus 로고
    • 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.
    • 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.
  • 31
    • 0023947609 scopus 로고
    • Expression and site-directed mutagenesis of human dihydrofolate reductase
    • Prendergast, N. J.; Delcamp, T. J.; Smith, P. L.; Freisheim, J. H. Expression and site-directed mutagenesis of human dihydrofolate reductase. Biochemistry 1988, 27, 3664-3671.
    • (1988) Biochemistry , vol.27 , pp. 3664-3671
    • Prendergast, N.J.1    Delcamp, T.J.2    Smith, P.L.3    Freisheim, J.H.4
  • 32
    • 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
  • 33
    • 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, 37, 1914-1923.
    • (1993) Antimicrob. Agents Chemother , vol.37 , pp. 1914-1923
    • Chio, L.C.1    Queener, S.F.2
  • 34
    • 0031277801 scopus 로고    scopus 로고
    • Identification and cloning of the Mycobacterium avium folA gene, required for dihydrofolate reductase activity
    • Zywno-van-Ginkel, S.; Dooley, T. P.; Suling, W. J.; Barrow, W. W. Identification and cloning of the Mycobacterium avium folA gene, required for dihydrofolate reductase activity. FEMS Microbiol. Lett. 1997, 156, 69-78.
    • (1997) FEMS Microbiol. Lett , vol.156 , pp. 69-78
    • Zywno-van-Ginkel, S.1    Dooley, T.P.2    Suling, W.J.3    Barrow, W.W.4
  • 35
    • 0032444693 scopus 로고    scopus 로고
    • Susceptibilities of Mycobacterium tuberculosis and Mycobacterium avium complex to lipophilic deazapteridine derivatives, inhibitors of dihydrofolate reductase
    • Suling, W. J.; Reynolds, R. C.; Barrow, E. W.; Wilson, L. N.; Piper, J. R.; Barrow, W. W. Susceptibilities of Mycobacterium tuberculosis and Mycobacterium avium complex to lipophilic deazapteridine derivatives, inhibitors of dihydrofolate reductase. J. Antimicrob. Chemother. 1998, 42, 811-815.
    • (1998) J. Antimicrob. Chemother , vol.42 , pp. 811-815
    • Suling, W.J.1    Reynolds, R.C.2    Barrow, E.W.3    Wilson, L.N.4    Piper, J.R.5    Barrow, W.W.6
  • 37
    • 0010427145 scopus 로고    scopus 로고
    • Bakerman, H. A. A method for measuring the microbiological activity of tetrahydrofolic acid and other labile reduced folic acid derivatives. Anal. Biochem. 1961, 2, 558-567.
    • Bakerman, H. A. A method for measuring the microbiological activity of tetrahydrofolic acid and other labile reduced folic acid derivatives. Anal. Biochem. 1961, 2, 558-567.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.