메뉴 건너뛰기




Volumn 24, Issue 10-12, 2005, Pages 1543-1568

Synthesis of 9-[1-(substituted)-3-(phosphonomethoxy)propyl]adenine derivatives as possible antiviral agents

Author keywords

Acyclic nucleosides; Antiviral; Prodrugs

Indexed keywords

1 TERT BUTYLDIMETHYLSILYL 4 PIVALOYLBUTAN 1,2,4 TRIOL; 9 [1 AMINOMETHYL [3 (DIISOPROPYLPHOSPHONO)METHOXY]PROPYL] N6 METHOXYTRITYLADENINE; 9 [1 AZIDOMETHYL (3 PHOSPHONOMETHOXY)PROPYL] N6 METHOXYTRITYLADENINE; 9 [1 AZIDOMETHYL [3 (DI TERT BUTYLCARBONYLOXYMETHYLPHOSPHONO)METHOXY] PROPYL] N6 METHOXYTRITYLADENINE; 9 [1 AZIDOMETHYL [3 (DIISOPROPYLPHOSPHONO)METHOXY]PROPYL] N6 METHOXYTRITYLADENINE; 9 [1 FLUOROMETHYL [3 (DIISOPROPYLPHOSPHONO)METHOXY]PROPYL] N6 METHOXYTRITYLADENINE; 9 [1 HYDROXYMETHYL [3 (DIISOPROPYLPHOSPHONO)METHOXY]PROPYL] N6 METHOXYTRITYLADENINE; 9 [1 METHOXYMETHYL (3 PHOSPHONOMETHOXY)PROPYL] N6 METHOXYTRITYLADENINE; 9 [1 METHOXYMETHYL [3 (DI TERT BUTYLCARBONYLOXYMETHYLPHOSPHONO)METHOXY] PROPYL] N6 METHOXYTRITYLADENINE; 9 [1 METHOXYTRITYLAMINOMETHYL [3 (DIISOPROPYLPHOSPHONO)METHOXY]PROPYL] N6 METHOXYTRITYLADENINE; 9 [1 METHOXYTRITYLOXYMETHYL (3 PHOSPHONOMETHOXY)PROPYL] N6 METHOXYTRITYLADENINE; 9 [1 METHOXYTRITYLOXYMETHYL [3 (DI TERT BUTYLCARBONYLOXYMETHYLPHOSPHONO) METHOXY]PROPYL] N6 METHOXYTRITYLADENINE; 9 [1 METHOXYTRITYLOXYMETHYL [3 (DIISOPROPYLPHOSPHONO)METHOXY]PROPYL] N6 METHOXYTRITYLADENINE; 9 [1 METHYL (3 PHOSPHONOMETHOXY)PROPYL] N6 METHOXYTRITYLADENINE; 9 [1 METHYL [3 (DI TERT BUTYLCARBONYLOXYMETHYLPHOSPHONO)METHOXY]PROPYL] N6 METHOXYTRITYLADENINE; 9 [1 METHYLENE (3 PHOSPHONOMETHOXY)PROPYL] N6 METHOXYTRITYLADENINE; 9 [1 METHYLENE [3 (DIISOPROPYLPHOSPHONO)METHOXY]PROPYL] N6 METHOXYTRITYLADENINE; 9 [1 N METHOXYTRITYLAMINOMETHYL (3 PHOSPHONOMETHOXY)PROPYL] N6 METHOXYTRITYLADENINE; 9 [1 N METHOXYTRITYLAMINOMETHYL [3 (DI TERT BUTYLCARBONYLOXYMETHYLPHOSPHONO)METHOXY]PROPYL] N6 METHOXYTRITYLADENINE; 9 [1 TOSYLOXYMETHYL [3 (DIISOPROPYLPHOSPHONO)METHOXY]PROPYL] N6 METHOXYTRITYLADENINE; 9 [[1 (ALPHA METHOXYTRITYLOXY)ETHYL][3 (DI TERT BUTYLCARBONYLOXYMETHYLPHOSPHONO)METHOXY]PROPYL] N6 METHOXYTRITYLADENINE; ADENINE; ADENINE DERIVATIVE; ANTIVIRUS AGENT; BUTANE; HYDROXYL GROUP; PHOSPHORUS DERIVATIVE; PRODRUG; SILICON DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; DRUG DERIVATIVE; PHOSPHONIC ACID DERIVATIVE;

EID: 29244458686     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1080/15257770500268673     Document Type: Article
Times cited : (4)

References (37)
  • 1
    • 0033054813 scopus 로고    scopus 로고
    • EASL International Consensus Conference on Hepatitis C, Paris, 26-28 February 1999, Consensus Statement
    • Consensus Panel. EASL International Consensus Conference on Hepatitis C, Paris, 26-28 February 1999, Consensus Statement. J. Hepatol. 1999, 30, 956.
    • (1999) J. Hepatol. , vol.30 , pp. 956
  • 2
    • 0033516384 scopus 로고    scopus 로고
    • The scientific challenge of hepatitis C
    • (a) Cohen, J. The scientific challenge of hepatitis C. Science 1999, 285, 26;
    • (1999) Science , vol.285 , pp. 26
    • Cohen, J.1
  • 3
    • 0000361013 scopus 로고    scopus 로고
    • Fields, B.N., Knipe, D.M., Howley, P.M., Eds.; Raven: New York
    • (b) Houghten, M. In Virology; Fields, B.N., Knipe, D.M., Howley, P.M., Eds.; Raven: New York, 1996; 1035-1058;
    • (1996) Virology , pp. 1035-1058
    • Houghten, M.1
  • 4
    • 0027942956 scopus 로고
    • Hepatitis C: Progress and problems
    • (c) Cuthbert, J.A. Hepatitis C: Progress and problems. Clin. Microbiol. Rev. 1994, 7(4), 505-532.
    • (1994) Clin. Microbiol. Rev. , vol.7 , Issue.4 , pp. 505-532
    • Cuthbert, J.A.1
  • 5
    • 0035027046 scopus 로고    scopus 로고
    • Emerging therapies for hepatitis C infection
    • and references cited therein
    • Dymock, B.W. Emerging therapies for hepatitis C infection. Emerging Drugs 2001, 6(1), 13-42, and references cited therein.
    • (2001) Emerging Drugs , vol.6 , Issue.1 , pp. 13-42
    • Dymock, B.W.1
  • 8
    • 0018645586 scopus 로고
    • The activity in vitro against herpes virus of 9-(2-hydroxyethoxymethyl) guanine (acycloguanosine), a new antiviral agent
    • (c) Collins, P.; Bauer, D.J. The activity in vitro against herpes virus of 9-(2-hydroxyethoxymethyl)guanine (acycloguanosine), a new antiviral agent. J. Antimicrob. Chemother. 1979, 5(4), 431-436.
    • (1979) J. Antimicrob. Chemother. , vol.5 , Issue.4 , pp. 431-436
    • Collins, P.1    Bauer, D.J.2
  • 9
    • 0020316367 scopus 로고
    • A new nucleoside analog, 9-[[2-hydroxy-1-(hydroxymethyl)ethoxy]methyl] guanine, highly active in vitro against herpes simplex virus types 1 and 2
    • (a) Smith, K.O.; Galloway, K.S.; Kennell, W.L.; Ogilvie, K.K.; Radatus, B.K. A new nucleoside analog, 9-[[2-hydroxy-1-(hydroxymethyl)ethoxy]methyl] guanine, highly active in vitro against herpes simplex virus types 1 and 2. Antimicrob. Agents Chemother. 1982, 22(1), 55-61;
    • (1982) Antimicrob. Agents Chemother. , vol.22 , Issue.1 , pp. 55-61
    • Smith, K.O.1    Galloway, K.S.2    Kennell, W.L.3    Ogilvie, K.K.4    Radatus, B.K.5
  • 10
    • 0020261015 scopus 로고
    • Activation by thymidine kinase and potent antiherpetic activity of 2′-nor-2′-deoxyguanosine (2′NDG)
    • (b) Ashton, W.T.; Karkas, J.D.; Field, A.K.; Tolman, R.L. Activation by thymidine kinase and potent antiherpetic activity of 2′-nor-2′- deoxyguanosine (2′NDG). Biochem. Biophys. Res. Commun. 1982, 108(4), 1716-1721;
    • (1982) Biochem. Biophys. Res. Commun. , vol.108 , Issue.4 , pp. 1716-1721
    • Ashton, W.T.1    Karkas, J.D.2    Field, A.K.3    Tolman, R.L.4
  • 11
    • 0020636893 scopus 로고
    • 9-[(1,3-Dihydroxy-2-propoxy)methyl]guanine: A new potent and selective antiherpes agent
    • (c) Martin, J.C.; Dvorak, C.A.; Smee, D.F.; Matthews, T.R.; Verheyden, J.P.H. 9-[(1,3-Dihydroxy-2-propoxy)methyl]guanine: A new potent and selective antiherpes agent. J. Med. Chem. 1983, 26(5), 759-761;
    • (1983) J. Med. Chem. , vol.26 , Issue.5 , pp. 759-761
    • Martin, J.C.1    Dvorak, C.A.2    Smee, D.F.3    Matthews, T.R.4    Verheyden, J.P.H.5
  • 13
    • 0002391736 scopus 로고
    • Unique spectrum of activity of 9-[(1,3-dihydroxy-2-propoxy)methyl]- guanine against herpesviruses in vitro and its mode of action against herpes simplex virus type 1
    • U.S.A.
    • (a) Cheng, Y.-C.; Huang, E.-S.; Lin, J.-C.; Mar, E.-C.; Pagano, J.S.; Dutschman, G.E.; Grill, S.P. Unique spectrum of activity of 9-[(1,3-dihydroxy-2- propoxy)methyl]-guanine against herpesviruses in vitro and its mode of action against herpes simplex virus type 1. Proc. Natl. Acad. Sci. U.S.A. 1983, 80(9), 2767-2770;
    • (1983) Proc. Natl. Acad. Sci. , vol.80 , Issue.9 , pp. 2767-2770
    • Cheng, Y.-C.1    Huang, E.-S.2    Lin, J.-C.3    Mar, E.-C.4    Pagano, J.S.5    Dutschman, G.E.6    Grill, S.P.7
  • 15
    • 0020614981 scopus 로고
    • Anti-herpesvirus activity of the acyclic nucleoside 9-(1,3-dihydroxy-2- propoxymethyl)guanine
    • Smee, D.F.; Martin, J.C.; Verheyden, J.P.H.; Matthews, T.R. Anti-herpesvirus activity of the acyclic nucleoside 9-(1,3-dihydroxy-2- propoxymethyl)guanine. Antimicrob. Agents Chemother. 1983, 23(5), 676-682.
    • (1983) Antimicrob. Agents Chemother. , vol.23 , Issue.5 , pp. 676-682
    • Smee, D.F.1    Martin, J.C.2    Verheyden, J.P.H.3    Matthews, T.R.4
  • 16
    • 0032997095 scopus 로고    scopus 로고
    • Clinical pharmacokinetics of the antiviral nucleotide analogues Cidofovir and Adefovir
    • Cundy, K.C. Clinical pharmacokinetics of the antiviral nucleotide analogues Cidofovir and Adefovir. Clin. Pharmacokinet. 1999, 36, 127-143.
    • (1999) Clin. Pharmacokinet. , vol.36 , pp. 127-143
    • Cundy, K.C.1
  • 17
    • 0023194835 scopus 로고
    • Phosphonylmethyl analogs of nucleotides and their derivatives: Chemistry and biology
    • Holy, A. Phosphonylmethyl analogs of nucleotides and their derivatives: Chemistry and biology. Nucleosides Nucleotides 1987, 6(1&2), 147-155.
    • (1987) Nucleosides Nucleotides , vol.6 , Issue.1-2 , pp. 147-155
    • Holy, A.1
  • 18
    • 0025247710 scopus 로고
    • Acyclic purine phosphonate analogues as antiviral agents. Synthesis and structure-activity relationships
    • Kim, C.U.; Luh, B.Y.; Misco, P.F.; Bronson, J.J.; Hitchcock, M.J.M.; Ghazzouli, I.; Martin, J.C. 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    Martin, J.C.7
  • 21
    • 0025781479 scopus 로고
    • Activity of acyclic nucleoside phosphonate analogues against human immunodeficiency virus in monocyte/macrophages and peripheral blood lymphocytes
    • Balzarini, J.; Perno, C.F.; Schols, D.; De Clercq, E. Activity of acyclic nucleoside phosphonate analogues against human immunodeficiency virus in monocyte/macrophages and peripheral blood lymphocytes. Biochem. Biophys. Res. Commun. 1991, 178, 329-335.
    • (1991) Biochem. Biophys. Res. Commun. , vol.178 , pp. 329-335
    • Balzarini, J.1    Perno, C.F.2    Schols, D.3    De Clercq, E.4
  • 23
    • 0030778137 scopus 로고    scopus 로고
    • Therapeutic potential of HPMPC (Cidofovir), PMEA (Adefovir) and related acyclic nucleoside phosphonate analogues as broad-spectrum antiviral agents
    • Naesens, L.; De Clercq, E. Therapeutic potential of HPMPC (Cidofovir), PMEA (Adefovir) and related acyclic nucleoside phosphonate analogues as broad-spectrum antiviral agents. Nucleosides Nucleotides 1997, 16, 983-992.
    • (1997) Nucleosides Nucleotides , vol.16 , pp. 983-992
    • Naesens, L.1    De Clercq, E.2
  • 24
    • 0027534661 scopus 로고
    • Differential antiherpesvirus and antiretrovirus effects of the (S) and (R) enantiomers of acyclic nucleoside phosphonates: Potent and selective in vitro and in vivo antiretrovirus activities of (R)-9-(2-phosphonomethoxypropyl)- 2,6-diaminopurine
    • Balzarini, J.; Holy, A.; Jindrich, J.; Naesens, L.; Snoeck, R.; Schols, D.; De Clercq, E. Differential antiherpesvirus and antiretrovirus effects of the (S) and (R) enantiomers of acyclic nucleoside phosphonates: Potent and selective in vitro and in vivo antiretrovirus activities of (R)-9-(2- phosphonomethoxypropyl)-2,6-diaminopurine. Antimicrob. Agents Chemother. 1993, 37, 332-338.
    • (1993) Antimicrob. Agents Chemother. , vol.37 , pp. 332-338
    • Balzarini, J.1    Holy, A.2    Jindrich, J.3    Naesens, L.4    Snoeck, R.5    Schols, D.6    De Clercq, E.7
  • 25
    • 0029989972 scopus 로고    scopus 로고
    • Activity of the (R)-enantiomers of 9-(2-phosphonyl-methoxypropyl)adenine and 9-(2-phosphonyl-methoxypropyl)-2,6-diaminopurine against human immunodeficiency virus in different human cell systems
    • Balzarini, J.; Aquaro, S.; Perno, C.-F.; Holy, A.; De Clercq, E. Activity of the (R)-enantiomers of 9-(2-phosphonyl-methoxypropyl)adenine and 9-(2-phosphonyl-methoxypropyl)-2,6-diaminopurine against human immunodeficiency virus in different human cell systems. Biochem. Biophys. Res. Commun. 1996, 219, 337-341.
    • (1996) Biochem. Biophys. Res. Commun. , vol.219 , pp. 337-341
    • Balzarini, J.1    Aquaro, S.2    Perno, C.-F.3    Holy, A.4    De Clercq, E.5
  • 26
    • 0345004991 scopus 로고    scopus 로고
    • Structure-antiviral activity relationship in the series of pyrimidine and purine N-[2-(2-phosphonomethoxy) ethyl] nucleotide analogues. 1. Derivatives substituted at the carbon atoms of the base
    • Holy, A.; Gunter, J.; Dvorakova, H.; Masojidkova, M.; Andrei, G.; Snoeck, R.; Balzarini, J.; De Clercq, E. Structure-antiviral activity relationship in the series of pyrimidine and purine N-[2-(2-phosphonomethoxy) ethyl] nucleotide analogues. 1. Derivatives substituted at the carbon atoms of the base. J. Med. Chem. 1999, 42, 2064-2086.
    • (1999) J. Med. Chem. , vol.42 , pp. 2064-2086
    • Holy, A.1    Gunter, J.2    Dvorakova, H.3    Masojidkova, M.4    Andrei, G.5    Snoeck, R.6    Balzarini, J.7    De Clercq, E.8
  • 28
    • 0026675873 scopus 로고
    • Synthesis of racemic carboacyclonucleosides derived from butane-1,4-diol and hexane-1,6-diol
    • Perbost, M.; Lucas, M.; Chavis, C.; Imbach, J.-L. Synthesis of racemic carboacyclonucleosides derived from butane-1,4-diol and hexane-1,6-diol. Nucleosides Nucleotides 1992, 11(8), 1489-1505.
    • (1992) Nucleosides Nucleotides , vol.11 , Issue.8 , pp. 1489-1505
    • Perbost, M.1    Lucas, M.2    Chavis, C.3    Imbach, J.-L.4
  • 29
    • 0026672490 scopus 로고
    • An expeditious synthesis of homochiral (R) 2-(9-purinyl)butane-1,4-diols from (S) butane-1,2,4-triol
    • Perbost, M.; Lucas, M.; Chavis, C.; Imbach, J.-L. An expeditious synthesis of homochiral (R) 2-(9-purinyl)butane-1,4-diols from (S) butane-1,2,4-triol. Nucleosides Nucleotides 1992, 11(8), 1529-1537.
    • (1992) Nucleosides Nucleotides , vol.11 , Issue.8 , pp. 1529-1537
    • Perbost, M.1    Lucas, M.2    Chavis, C.3    Imbach, J.-L.4
  • 30
    • 0034647731 scopus 로고    scopus 로고
    • Synthesis of acyclic nucleoside and nucleotide analogues from amino acids: A convenient approach to a PMEA-PMPA hybrid
    • Jeffery, A.L.; Kim, J.-H.; Wiemer, D.F. Synthesis of acyclic nucleoside and nucleotide analogues from amino acids: A convenient approach to a PMEA-PMPA hybrid. Tetrahedron 2000, 56, 5077-5083.
    • (2000) Tetrahedron , vol.56 , pp. 5077-5083
    • Jeffery, A.L.1    Kim, J.-H.2    Wiemer, D.F.3
  • 32
    • 0000569383 scopus 로고
    • Facile access to (S)-1,2,4-butanetriol and its derivatives
    • Hanessian, S.; Ugolini, A.; Dube, D.; Glamyan, A. Facile access to (S)-1,2,4-butanetriol and its derivatives. Can. J. Chem. 1984, 62, 2146-2147.
    • (1984) Can. J. Chem. , vol.62 , pp. 2146-2147
    • Hanessian, S.1    Ugolini, A.2    Dube, D.3    Glamyan, A.4
  • 33
    • 84985650846 scopus 로고
    • Stereoselective additions of chiral, functionalized organozinc reagents to achiral and chiral aldehydes: Matched-mismatched case in organozinc chemistry
    • Koert, U.; Wagner, H.; Pidun, U. Stereoselective additions of chiral, functionalized organozinc reagents to achiral and chiral aldehydes: Matched-mismatched case in organozinc chemistry. Chem. Ber. 1994, 127(8), 1447-1457.
    • (1994) Chem. Ber. , vol.127 , Issue.8 , pp. 1447-1457
    • Koert, U.1    Wagner, H.2    Pidun, U.3
  • 34
    • 0030597014 scopus 로고    scopus 로고
    • Synthesis and antiviral activity of acyclic analogues of 1,5-anhydrohexitol nucleosides using mitsunobu reaction
    • Hossain, N.; Rozenski, J.; De Clercq, E.; Herdewijn, P. Synthesis and antiviral activity of acyclic analogues of 1,5-anhydrohexitol nucleosides using mitsunobu reaction. Tetrahedron 1996, 52(43), 13655-13670.
    • (1996) Tetrahedron , vol.52 , Issue.43 , pp. 13655-13670
    • Hossain, N.1    Rozenski, J.2    De Clercq, E.3    Herdewijn, P.4
  • 35
    • 0001171156 scopus 로고
    • Purine nucleosides. VIII. Reinvestigation of the position of glycosidation in certain synthetic "7"-substituted 6-dimethylaminopurine nucleosides related to puromycin
    • Townsend, L.B.; Robins, R.K.; Loeppky, R.N.; Leonard, N.J. Purine nucleosides. VIII. Reinvestigation of the position of glycosidation in certain synthetic "7"-substituted 6-dimethylaminopurine nucleosides related to puromycin. J. Am. Chem. Soc. 1964, 86, 5320-5325.
    • (1964) J. Am. Chem. Soc. , vol.86 , pp. 5320-5325
    • Townsend, L.B.1    Robins, R.K.2    Loeppky, R.N.3    Leonard, N.J.4
  • 36
    • 37049073108 scopus 로고
    • Enzymatic preparation of enantiomerically pure and selectively protected 1,2- and 1,3-diols
    • Goergens, U.; Schneider, M.P. Enzymatic preparation of enantiomerically pure and selectively protected 1,2- and 1,3-diols. J. Chem. Soc. Chem. Commun. 1991, 16, 1066-1068.
    • (1991) J. Chem. Soc. Chem. Commun. , vol.16 , pp. 1066-1068
    • Goergens, U.1    Schneider, M.P.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.