메뉴 건너뛰기




Volumn 39, Issue 5, 1996, Pages 1130-1135

Synthesis and biological evaluation of 1′,2′-seconucleo-5′-phosphonates

Author keywords

[No Author keywords available]

Indexed keywords

1',2' SECONUCLEOTIDE 5' PHOSPHONATE; ANTIVIRUS AGENT; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0029879333     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9506783     Document Type: Article
Times cited : (19)

References (27)
  • 1
    • 1542690351 scopus 로고
    • Phosphonates as Analogues of Natural Phosphates
    • (a) Engel, R. Phosphonates as Analogues of Natural Phosphates. Chem. Rev. 1977, 77, 349-367.
    • (1977) Chem. Rev. , vol.77 , pp. 349-367
    • Engel, R.1
  • 2
    • 0003742285 scopus 로고
    • Hilderband, R. L., Ed.; CRC Press, Inc.: Boca Raton, FL
    • (b) Engel, R. In The Role of Phosphonates in Living Systems; Hilderband, R. L., Ed.; CRC Press, Inc.: Boca Raton, FL, 1983; pp 93-138.
    • (1983) The Role of Phosphonates in Living Systems , pp. 93-138
    • Engel, R.1
  • 4
    • 0009935874 scopus 로고
    • Synthesis of Acyclonucleoside Phosphonates for Evaluation as Antiviral Agents
    • Martin, J. E., Ed.; American Chemical Society: Washington, DC
    • Reist, E. J.; Sturm, P. A.; Pong, R. Y.; Tanga, M. J.; Sidwell, R. W. Synthesis of Acyclonucleoside Phosphonates for Evaluation as Antiviral Agents. In Nucleotide Analogues as Antiviral Agents; Martin, J. E., Ed.; American Chemical Society: Washington, DC, 1989; pp 17-34.
    • (1989) Nucleotide Analogues As Antiviral Agents , pp. 17-34
    • Reist, E.J.1    Sturm, P.A.2    Pong, R.Y.3    Tanga, M.J.4    Sidwell, R.W.5
  • 5
    • 85033840032 scopus 로고    scopus 로고
    • note
    • In the text, the naming and numbering of the 1′,2′-seconucleophosphonates follow nucleoside nomenclature; however, in the Experimental Section, the acyclic side chains of the title compounds are named and numbered in accordance with Chemical Abstracts Service nomenclature.
  • 6
    • 0025785730 scopus 로고
    • 5-Phosphoribosyl 1-Pyrophosphate Synthetase converts the Acyclic Nucleoside Phosphonates 9-(3-Hydroxy-2-phosphonylmethoxypropyl)- Adenine and 9-(2-Phosphonylmethoxyethyl)adenine directly to their Antivirally Active Diphosphate Derivatives
    • (a) Balzarini, J.; De Clercq, E. 5-Phosphoribosyl 1-Pyrophosphate Synthetase converts the Acyclic Nucleoside Phosphonates 9-(3-Hydroxy-2-phosphonylmethoxypropyl)- adenine and 9-(2-Phosphonylmethoxyethyl)adenine directly to their Antivirally Active Diphosphate Derivatives. J. Biol. Chem. 1991, 266, 8686-8689.
    • (1991) J. Biol. Chem. , vol.266 , pp. 8686-8689
    • Balzarini, J.1    De Clercq, E.2
  • 9
    • 0025247710 scopus 로고
    • Acyclic Purine Phosphonate Analogues as Antiviral Agents. Synthesis and Structure-Activity Relationships
    • (d) Kim, C. U.; Luh, B. Y.; Misco, P. F.; Bronson, J. J.; Hitchcock, M. J. M.; Ghazzouli, I. Acyclic Purine Phosphonate Analogues as Antiviral Agents. Synthesis and Structure-Activity Relationships. J. Med. Chem. 1990, 33, 1207-1213.
    • (1990) J. Med. Chem. , vol.33 , pp. 1207-1213
    • Kim, C.U.1    Luh, B.Y.2    Misco, P.F.3    Bronson, J.J.4    Hitchcock, M.J.M.5    Ghazzouli, I.6
  • 10
    • 0022461410 scopus 로고
    • Synthesis and Antiherpes Virus Activity of Phosphate and Phosphonate Derivatives of 9-[(1,3-Dihydroxy-2- Propoxy)methyl]-guanine
    • Prisbe, E. J.; Martin, J. C.; McGee, D. P. C.; Barker, M. F.; Smee, D. F.; Duke, A. E.; Matthews, T. R.; Verheyden, J. P. H. Synthesis and Antiherpes Virus Activity of Phosphate and Phosphonate Derivatives of 9-[(1,3-Dihydroxy-2- propoxy)methyl]-guanine. J. Med. Chem. 1985, 29, 671-675.
    • (1985) J. Med. Chem. , vol.29 , pp. 671-675
    • Prisbe, E.J.1    Martin, J.C.2    McGee, D.P.C.3    Barker, M.F.4    Smee, D.F.5    Duke, A.E.6    Matthews, T.R.7    Verheyden, J.P.H.8
  • 11
    • 84942222826 scopus 로고
    • Michaelis-Arbuzov-Und Perkow Reaktionen
    • Arbuzov, B. A. Michaelis-Arbuzov-Und Perkow Reaktionen. (Michaelis-Arbuzov-and Perkow Reactions.) Pure Appl. Chem. 1964, 9, 307-335.
    • (1964) Pure Appl. Chem. , vol.9 , pp. 307-335
    • Arbuzov, B.A.1
  • 13
    • 0028291074 scopus 로고
    • An Enantiospecific Synthesis of the Human Cytomegalovirus Antiviral Agent [(R)-3-((2-Amino-1,6-dihydro-6-oxo-9H-purine-9-yl)methoxy)-4-hydroxybutyl] phosphonic Acid
    • This synthetic approach was recently used in the preparation of the R-enantiomer of ganciclovir phosphonate; see: Chamberlain, S. D.; Biron, K. K.; Dornsife, R. E.; Averett, D. R.; Beauchamp, L.; Koszalka, G. W. An Enantiospecific Synthesis of the Human Cytomegalovirus Antiviral Agent [(R)-3-((2-Amino-1,6-dihydro-6-oxo-9H-purine-9-yl)methoxy)-4-hydroxybutyl] phosphonic Acid. J. Med. Chem. 1994, 37, 1371-1377.
    • (1994) J. Med. Chem. , vol.37 , pp. 1371-1377
    • Chamberlain, S.D.1    Biron, K.K.2    Dornsife, R.E.3    Averett, D.R.4    Beauchamp, L.5    Koszalka, G.W.6
  • 14
    • 0000240075 scopus 로고
    • General and Facile Synthesis of β- And γ-Hydroxy Phosphonates from Expoxides
    • Li, Z.; Racha, S.; Dan, L.; El-Subbagh, H. I.; Abushanab, E. A General and Facile Synthesis of β- and γ-Hydroxy Phosphonates from Expoxides. J. Org. Chem. 1993, 58, 5779-5783.
    • (1993) J. Org. Chem. , vol.58 , pp. 5779-5783
    • Li, Z.1    Racha, S.2    Dan, L.3    El-Subbagh, H.I.4    Abushanab, E.A.5
  • 16
    • 0000989744 scopus 로고
    • An Efficient Synthesis of 2-Deoxypentofuranoses
    • (b) Vargeese, C.; Abushanab, E. An Efficient Synthesis of 2-Deoxypentofuranoses. J. Org. Chem. 1990, 55, 4400-4403.
    • (1990) J. Org. Chem. , vol.55 , pp. 4400-4403
    • Vargeese, C.1    Abushanab, E.2
  • 17
    • 0023893197 scopus 로고
    • A Practical Synthesis of Ethyl 1,2,4-Triazole-3-Carboxylate and its use in the Formation of Chiral 1′,2′-Seconucleosides of Ribavirin
    • (a) Vemishetti, P.; Leiby, R. W.; Abushanab, E.; Panzica, R. P. A Practical Synthesis of Ethyl 1,2,4-Triazole-3-Carboxylate and its use in the Formation of Chiral 1′,2′-Seconucleosides of Ribavirin. J. Heterocycl. Chem. 1988, 25, 651-654.
    • (1988) J. Heterocycl. Chem. , vol.25 , pp. 651-654
    • Vemishetti, P.1    Leiby, R.W.2    Abushanab, E.3    Panzica, R.P.4
  • 18
    • 0025122141 scopus 로고
    • Preparation of 2′-Deoxy-2′-fluoro-1′,2′-seconucleosides as Potential Antiviral Agents
    • (b) Vemishetti, P.; Saibaba, R.; Panzica, R. P.; Abushanab, E. Preparation of 2′-Deoxy-2′-fluoro-1′,2′-seconucleosides as Potential Antiviral Agents. J. Med. Chem. 1990, 33, 681-686.
    • (1990) J. Med. Chem. , vol.33 , pp. 681-686
    • Vemishetti, P.1    Saibaba, R.2    Panzica, R.P.3    Abushanab, E.4
  • 19
    • 0024489962 scopus 로고
    • 1′,2′-Secodideoxynucleosides as Potential Anti-HIV Agents
    • Abushanab, E.; Sarma, M. S. P. 1′,2′-Secodideoxynucleosides as Potential Anti-HIV Agents. J. Med. Chem. 1989, 32, 76-79.
    • (1989) J. Med. Chem. , vol.32 , pp. 76-79
    • Abushanab, E.1    Sarma, M.S.P.2
  • 20
    • 0010631016 scopus 로고
    • Iodomethylsilane-A Versatile Synthetic Reagent
    • and references cited therein
    • Olah, G. A.; Narang, S. C. Iodomethylsilane-A Versatile Synthetic Reagent. Tetrahedron 1982, 38, 2226-2277 and references cited therein.
    • (1982) Tetrahedron , vol.38 , pp. 2226-2277
    • Olah, G.A.1    Narang, S.C.2
  • 21
    • 0001090548 scopus 로고
    • Dilithium Tetrabromonickelate (II) as a Source of Soft Nucleophilic Bromide: Reaction with Epoxides
    • Dawe, R. D.; Molinski, T. F.; Turner, J. V. Dilithium Tetrabromonickelate (II) as a Source of Soft Nucleophilic Bromide: Reaction with Epoxides. Tetrahedron Lett. 1984, 25, 2061-2064.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 2061-2064
    • Dawe, R.D.1    Molinski, T.F.2    Turner, J.V.3
  • 22
    • 0029154159 scopus 로고
    • Synthesis of Racemic 2-Phosphonomethyl-1,3,-dixoloane Nucleoside Analogues as Potential Antiviral Agents
    • Bednarski, K.; Dixit, D. M.; Mansour, T. S.; Colman, S. G.; Walcott, S. M.; Ashman, C. Synthesis of Racemic 2-Phosphonomethyl-1,3,-dixoloane Nucleoside Analogues as Potential Antiviral Agents. Bioorg. Med. Chem. Lett. 1995, 5, 1741-1744.
    • (1995) Bioorg. Med. Chem. Lett. , vol.5 , pp. 1741-1744
    • Bednarski, K.1    Dixit, D.M.2    Mansour, T.S.3    Colman, S.G.4    Walcott, S.M.5    Ashman, C.6
  • 23
    • 85033840359 scopus 로고    scopus 로고
    • note
    • 2N protons were not completely visible due to overlap with the HDO peak.
  • 26
    • 0021168019 scopus 로고
    • Synergistic Antiviral Effects of Ribavirin and the C-Nucleoside Analogs Tiazofurin and Seleazofurin Against Togaviruses, Bunyaviruses, and Arenaviruses
    • Huggins, J. W.; Robins, R. K.; Canonico, P. G. Synergistic Antiviral Effects of Ribavirin and the C-Nucleoside Analogs Tiazofurin and Seleazofurin Against Togaviruses, Bunyaviruses, and Arenaviruses. Antimicrob. Agents Chemother. 1984, 26, 476-480.
    • (1984) Antimicrob. Agents Chemother. , vol.26 , pp. 476-480
    • Huggins, J.W.1    Robins, R.K.2    Canonico, P.G.3
  • 27
    • 85033840406 scopus 로고    scopus 로고
    • note
    • Testing was conducted under the auspices of USAMRIID.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.