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Volumn 50, Issue 26, 2007, Pages 6485-6492

Synthesis and antiviral activity of the carbocyclic analogue of the highly potent and selective anti-VZV bicyclo furano pyrimidines

Author keywords

[No Author keywords available]

Indexed keywords

6 PENTYLPHENYLFURO[2,3 D]PYRIMIDINE 2' DEOXYRIBOSE; CARBOCYCLIC NUCLEOSIDE; DEOXYURIDINE; THYMIDINE KINASE; UNCLASSIFIED DRUG;

EID: 37349002731     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm070357e     Document Type: Article
Times cited : (24)

References (17)
  • 1
    • 0034727849 scopus 로고    scopus 로고
    • Highly potent and selective inhibition of varicella-zoster virus by bicyclic furopyrimidine nucleosides bearing an aryl side chain
    • McGuigan, C.; Barucki, H.; Blewett, S.; Carangio, A.; Erichsen, J. T.; Andrei, G.; Snoeck, R.; De Clercq, E.; Balzarini, J. Highly potent and selective inhibition of varicella-zoster virus by bicyclic furopyrimidine nucleosides bearing an aryl side chain. J. Med. Chem. 2000, 43, 4993-4997.
    • (2000) J. Med. Chem , vol.43 , pp. 4993-4997
    • McGuigan, C.1    Barucki, H.2    Blewett, S.3    Carangio, A.4    Erichsen, J.T.5    Andrei, G.6    Snoeck, R.7    De Clercq, E.8    Balzarini, J.9
  • 2
    • 0037130292 scopus 로고    scopus 로고
    • Chemotherapy of varicella-zoster virus by a novel class of highly specific anti-VZV bicyclic pyrimidine nucleosides
    • Balzarini, J.; McGuigan, C. Chemotherapy of varicella-zoster virus by a novel class of highly specific anti-VZV bicyclic pyrimidine nucleosides. Biochim. Biophys. Acta 2002, 1587, 287-295.
    • (2002) Biochim. Biophys. Acta , vol.1587 , pp. 287-295
    • Balzarini, J.1    McGuigan, C.2
  • 3
    • 0036236787 scopus 로고    scopus 로고
    • Lack of susceptibility of bicyclic nucleoside analogs, highly potent inhibitors of varicella-zoster virus, to the catabolic action of himidine Phosphorylase and dihydropyrimidine dehydrogenase
    • Balzarini, J.; Sienaert, R.; Liekens, S.; Van Kuilenburg, A.; Carangio, A.; Esnouf, R. Lack of susceptibility of bicyclic nucleoside analogs, highly potent inhibitors of varicella-zoster virus, to the catabolic action of himidine Phosphorylase and dihydropyrimidine dehydrogenase. Mol. Pharmacol. 2002, 61, 1140-1145.
    • (2002) Mol. Pharmacol , vol.61 , pp. 1140-1145
    • Balzarini, J.1    Sienaert, R.2    Liekens, S.3    Van Kuilenburg, A.4    Carangio, A.5    Esnouf, R.6
  • 5
    • 0024999263 scopus 로고
    • Cerium(IV)-mediated halogenation at C-5 of uracil derivatives
    • Asakura, J.; Robins, M. J. Cerium(IV)-mediated halogenation at C-5 of uracil derivatives. J. Org. Chem. 1990, 55, 4928-4933.
    • (1990) J. Org. Chem , vol.55 , pp. 4928-4933
    • Asakura, J.1    Robins, M.J.2
  • 6
    • 0029034409 scopus 로고    scopus 로고
    • Bray, B. L.; Dolan, S. C.; Halter, B.; Lackey, J. W.; Schilling, M. B.; Tapolczay, D. J. Improved procedures for the preparation of (+)-(1R, 2S,4R)-4-amino-2-hydroxy-1-hydroxymethyl cyclopentane. Tetrahedron Lett. 1995, 36, 4483-4486.
    • Bray, B. L.; Dolan, S. C.; Halter, B.; Lackey, J. W.; Schilling, M. B.; Tapolczay, D. J. Improved procedures for the preparation of (+)-(1R, 2S,4R)-4-amino-2-hydroxy-1-hydroxymethyl cyclopentane. Tetrahedron Lett. 1995, 36, 4483-4486.
  • 7
    • 0025058714 scopus 로고
    • Fluoro carbocyclic nucleosides: Synthesis and antiviral activity of 2′- and 6′-fluoro carbocyclic pyrimidine nucleosides including carbocyclic 1-(2-deoxy-2-fluoro- β-D-arabinofuranosyl)-5-methyluracil and carbocyclic 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-iodouracil
    • Borthwick, A. D.; Evans, D. N.; Kirk, B. E.; Biggadike, K.; Exall, A. M.; Youds, P.; Roberts, S. M.; Knight, D. J.; Coates, J. A. V. Fluoro carbocyclic nucleosides: synthesis and antiviral activity of 2′- and 6′-fluoro carbocyclic pyrimidine nucleosides including carbocyclic 1-(2-deoxy-2-fluoro- β-D-arabinofuranosyl)-5-methyluracil and carbocyclic 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-iodouracil. J. Med Chem. 1990, 33, 179-186.
    • (1990) J. Med Chem , vol.33 , pp. 179-186
    • Borthwick, A.D.1    Evans, D.N.2    Kirk, B.E.3    Biggadike, K.4    Exall, A.M.5    Youds, P.6    Roberts, S.M.7    Knight, D.J.8    Coates, J.A.V.9
  • 8
    • 0346456880 scopus 로고    scopus 로고
    • Experimental and structural evidences that herpes 1 kinase and cellular DNA polymerase(s) discriminate on the basis of sugar pucker
    • Marquez, V. E.; Ben-Kasus, T.; Barchi, J. J., Jr.; Green, K. M.; Nicklaus, M. C.; Agbaria, R. Experimental and structural evidences that herpes 1 kinase and cellular DNA polymerase(s) discriminate on the basis of sugar pucker. J. Am. Chem. Soc. 2004, 126, 543-549.
    • (2004) J. Am. Chem. Soc , vol.126 , pp. 543-549
    • Marquez, V.E.1    Ben-Kasus, T.2    Barchi Jr., J.J.3    Green, K.M.4    Nicklaus, M.C.5    Agbaria, R.6
  • 9
    • 27544433014 scopus 로고    scopus 로고
    • Understanding how the herpes himidine kinase orchestrates optimal sugar and nucleobase conformations to accommodate its substrate at the active site: A chemical approach
    • Marquez, V. E.; Choi, Y.; Comin, M. J.; Russ, P.; George, C.; Huleihel, M.; Ben-Kasus, T.; Agbaria, R. Understanding how the herpes himidine kinase orchestrates optimal sugar and nucleobase conformations to accommodate its substrate at the active site: A chemical approach. J. Am. Chem. Soc. 2005, 127, 15145-15150.
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 15145-15150
    • Marquez, V.E.1    Choi, Y.2    Comin, M.J.3    Russ, P.4    George, C.5    Huleihel, M.6    Ben-Kasus, T.7    Agbaria, R.8
  • 10
    • 0015913888 scopus 로고
    • Conformational analysis of the sugar ring in nucleosides and nucleotides. Improved method for the interpretation of proton magnetic resonance coupling constants
    • Altona, C.; Sundarlingam, M. Conformational analysis of the sugar ring in nucleosides and nucleotides. Improved method for the interpretation of proton magnetic resonance coupling constants. J. Am. Chem. Soc. 1973, 95, 2333-2344.
    • (1973) J. Am. Chem. Soc , vol.95 , pp. 2333-2344
    • Altona, C.1    Sundarlingam, M.2
  • 11
    • 12844286981 scopus 로고    scopus 로고
    • NMR conformational analysis of p-tolyl furanopyrimidine 2′-deoxyribonucleoside and crystal structure of its 3′,5′-di-O-acetyl derivative
    • Esho, N.; Desauliners, J. P.; Davies, B.; Chui, H. M. P.; Rao, M. S.; Chow, C. S.; Szafert, S.; Dembinski, R. NMR conformational analysis of p-tolyl furanopyrimidine 2′-deoxyribonucleoside and crystal structure of its 3′,5′-di-O-acetyl derivative. Bioorg. Med Chem. 2005, 13, 1231-1238.
    • (2005) Bioorg. Med Chem , vol.13 , pp. 1231-1238
    • Esho, N.1    Desauliners, J.P.2    Davies, B.3    Chui, H.M.P.4    Rao, M.S.5    Chow, C.S.6    Szafert, S.7    Dembinski, R.8
  • 12
    • 37049095416 scopus 로고
    • Determination of glycosidic bond conformation of pyrimidine nucleosides and nucleotides using vicinal carbon-proton coupling constants
    • Davies, D. B.; Rajani, P.; Sadikot, H. Determination of glycosidic bond conformation of pyrimidine nucleosides and nucleotides using vicinal carbon-proton coupling constants. J. Chem. Soc., Perkin Trans. 2 1985, 2, 279-285.
    • (1985) J. Chem. Soc., Perkin Trans. 2 , vol.2 , pp. 279-285
    • Davies, D.B.1    Rajani, P.2    Sadikot, H.3
  • 13
    • 0037467381 scopus 로고    scopus 로고
    • DFT analysis of NMR scalr interactions across the glycosidic bond in DNA
    • Munzarová, M. L.; Sklenár, V. DFT analysis of NMR scalr interactions across the glycosidic bond in DNA. J. Am. Chem. Soc. 2003, 125, 3649-3658.
    • (2003) J. Am. Chem. Soc , vol.125 , pp. 3649-3658
    • Munzarová, M.L.1    Sklenár, V.2
  • 14
    • 49349134796 scopus 로고
    • Conformations of nucleosides and nucleotides
    • Davies, D. B. Conformations of nucleosides and nucleotides. Prog. Nucl. Magn. Reson. Spectrosc. 1978, 12, 135-225.
    • (1978) Prog. Nucl. Magn. Reson. Spectrosc , vol.12 , pp. 135-225
    • Davies, D.B.1
  • 15
    • 0036909167 scopus 로고    scopus 로고
    • The conformational study of two carbocyclic nucleosides: Why carbocyclic nucleic acids (CarNAs) form more stable duplexes with rNA than DNA does
    • Xu, Y.; Kino, K.; Sugiyama, H. The conformational study of two carbocyclic nucleosides: Why carbocyclic nucleic acids (CarNAs) form more stable duplexes with rNA than DNA does. J. Biomol. Struct. Dyn. 2002, 20, 437-446.
    • (2002) J. Biomol. Struct. Dyn , vol.20 , pp. 437-446
    • Xu, Y.1    Kino, K.2    Sugiyama, H.3
  • 16
    • 0023604906 scopus 로고
    • The synthesis and antiviral properties of (E)-5-(2- bromovinyl)-2′-deoxyuridine-related compounds
    • Ashwell, M.; Jones, S.; Kumar, A.; Sayers, J. R.; Walker, R. T.; Sakuma, T.; De Clercq, E. The synthesis and antiviral properties of (E)-5-(2- bromovinyl)-2′-deoxyuridine-related compounds. Tetrahedron 1987, 43, 4601-4608.
    • (1987) Tetrahedron , vol.43 , pp. 4601-4608
    • Ashwell, M.1    Jones, S.2    Kumar, A.3    Sayers, J.R.4    Walker, R.T.5    Sakuma, T.6    De Clercq, E.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.