메뉴 건너뛰기




Volumn 23, Issue 1-2, 2004, Pages 347-359

Nucleosides. IX. Synthesis of Purine N3,5′ -Cyclonucleosides and N3,5′-Cyclo-2′,3′ -seconucleosides via Mitsunobu Reaction as TIBO-like Derivativest

Author keywords

Formycin B; Mitsunobu reaction; N 3,5 cyclo 2 , 3 seconucleoside; N3,5 cyclonucleoside; TIBO

Indexed keywords

4,5,6,7 TETRAHYDRO 5 METHYLIMIDAZO[4,5,1 JK][1,4]BENZODIAZEPINE 2(1H) ONE; BENZODIAZEPINE DERIVATIVE; DEOXYINOSINE; FORMYCIN B; N3,5' CYCLO 2' DEOXYINOSINE; N3,5' CYCLO 2',3' SECONUCLEOSIDE; N3,5' CYCLO N2 TRIPHENYLPHOSPHORANYLIDENEGUANOSINE; N3,5' CYCLOINOSINE; N3,5' CYCLONUCLEOSIDE; N3,5' CYCLOXANTHOSINE; NUCLEOSIDE DERIVATIVE; PERIODATE SODIUM; RIBOSE; UNCLASSIFIED DRUG;

EID: 1542679040     PISSN: 15257770     EISSN: None     Source Type: Journal    
DOI: 10.1081/NCN-120027904     Document Type: Article
Times cited : (16)

References (36)
  • 1
    • 0029943676 scopus 로고    scopus 로고
    • Nucleosides. 8. Synthesis of 2′,3′-dideoxy- and 2′,3′-didehydro-2′,3′-dideoxyisoguanosine as potential antiretroviral agents
    • Chen, C.-S.; Chern, J.-W. Nucleosides. 8. Synthesis of 2′,3′-dideoxy- and 2′,3′-didehydro-2′,3′ -dideoxyisoguanosine as potential antiretroviral agents. Nucleosides Nucleotides 1996, 15, 1253.
    • (1996) Nucleosides Nucleotides , vol.15 , pp. 1253
    • Chen, C.-S.1    Chern, J.-W.2
  • 2
    • 0346207528 scopus 로고    scopus 로고
    • Comparative quantitative structure-activity relationship studies on anti-HIV drugs
    • Garg, R.; Gupta, S.P.; Gao, H.; Babu, M.S.; Debnath, A.K.; Hansch, C. Comparative quantitative structure-activity relationship studies on anti-HIV drugs. Chem. Rev. 1999, 99, 3525.
    • (1999) Chem. Rev. , vol.99 , pp. 3525
    • Garg, R.1    Gupta, S.P.2    Gao, H.3    Babu, M.S.4    Debnath, A.K.5    Hansch, C.6
  • 7
    • 0025971874 scopus 로고
    • Molecular structure of a potent HIV-1 inhibitor belonging to the TIBO family
    • Liaw, Y.-C.; Gao, Y.-G.; Robinson, H.; Wang, A.H.-J. Molecular structure of a potent HIV-1 inhibitor belonging to the TIBO family. J. Am. Chem. Soc. 1991, 113, 1857.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 1857
    • Liaw, Y.-C.1    Gao, Y.-G.2    Robinson, H.3    Wang, A.H.-J.4
  • 8
    • 0027081165 scopus 로고
    • Synthesis and antiviral activity of some new S-adenosyl-L-homocysteine derivatives
    • Serafinowski, P.; Dorland, E.; Harrap, K.R. Synthesis and antiviral activity of some new S-adenosyl-L-homocysteine derivatives. J. Med. Chem. 1992, 35, 4576.
    • (1992) J. Med. Chem. , vol.35 , pp. 4576
    • Serafinowski, P.1    Dorland, E.2    Harrap, K.R.3
  • 9
    • 0022386908 scopus 로고
    • Convienient preparation of S-adenosylhomocysteine and its analogues
    • Serafinowskim, P.A. Convienient preparation of S-adenosylhomocysteine and its analogues. Synthesis 1985, 926.
    • (1985) Synthesis , pp. 926
    • Serafinowskim, P.A.1
  • 11
    • 37049170598 scopus 로고
    • Nucleosides. Part VIII. Cyclonucleoside salts. A novel rearrangement of some toluene-p-sulphonylnucleosides
    • Clark, V.M.; Todd, A.R.; Zussman, J. Nucleosides. Part VIII. Cyclonucleoside salts. A novel rearrangement of some toluene-p-sulphonylnucleosides. J. Chem. Soc. 1951, 2952.
    • (1951) J. Chem. Soc. , pp. 2952
    • Clark, V.M.1    Todd, A.R.2    Zussman, J.3
  • 12
    • 1542398266 scopus 로고
    • The partial synthesis of ribose nucleotides. II. Muscle inosinic acid
    • Levene, P.A.; Tipson, R.S. The partial synthesis of ribose nucleotides. II. Muscle inosinic acid. J. Biol. Chem. 1935, 111, 313.
    • (1935) J. Biol. Chem. , vol.111 , pp. 313
    • Levene, P.A.1    Tipson, R.S.2
  • 14
    • 84985582620 scopus 로고
    • Nucleoside transformations. 8. Reactions of nucleosides with the triphenylphosphane/diethylazodicarboxylate system
    • Mengel, R.; Bartke, M. Nucleoside transformations. 8. Reactions of nucleosides with the triphenylphosphane/diethylazodicarboxylate system. Angew. Chem., Int. Ed. Engl. 1978, 17, 679.
    • (1978) Angew. Chem., Int. Ed. Engl. , vol.17 , pp. 679
    • Mengel, R.1    Bartke, M.2
  • 15
    • 0028825671 scopus 로고
    • Nucleosides 7. Synthesis of N-triphenylphosphoranylidene nucleosides by Mitsunobu reaction-a novel protecting group for primary amines of nucleosides
    • Chien, T.-C.; Chen, C.-S.; Yeh, J.-Y.; Wang, K.-C.; Chern, J.-W. Nucleosides 7. Synthesis of N-triphenylphosphoranylidene nucleosides by Mitsunobu reaction-a novel protecting group for primary amines of nucleosides. Tetrahedron Lett. 1995, 43, 7881.
    • (1995) Tetrahedron Lett. , vol.43 , pp. 7881
    • Chien, T.-C.1    Chen, C.-S.2    Yeh, J.-Y.3    Wang, K.-C.4    Chern, J.-W.5
  • 16
    • 0025188174 scopus 로고
    • Syn-anti conformational analysis of regular and modified nucleosides by 1D 1H NOE difference spectroscopy: A simple graphical method based on conformationally rigid molecules
    • Rosemeyer, H.; Tõth, G.; Golankiewicz, B.; Kazimierczuk, Z.; Bourgeois, W.; Kretschmer, U.; Muth, H.-P.; Seela, F. Syn-anti conformational analysis of regular and modified nucleosides by 1D 1H NOE difference spectroscopy: a simple graphical method based on conformationally rigid molecules. J. Org. Chem. 1990, 55, 5784.
    • (1990) J. Org. Chem. , vol.55 , pp. 5784
    • Rosemeyer, H.1    Tõth, G.2    Golankiewicz, B.3    Kazimierczuk, Z.4    Bourgeois, W.5    Kretschmer, U.6    Muth, H.-P.7    Seela, F.8
  • 17
    • 0010508759 scopus 로고
    • Potential anticancer agents. LI. Synthesis of 2-amino-9-(5′ -deoxy-β-D-ribofuranosyl)-9-H-purine-6-thiol
    • Reist, E.J.; Hart, P.A.; Goodman, L.; Baker, B.R. Potential anticancer agents. LI. Synthesis of 2-amino-9-(5′-deoxy-β -D-ribofuranosyl)-9-H-purine-6-thiol. J. Org. Chem. 1961, 26, 1557.
    • (1961) J. Org. Chem. , vol.26 , pp. 1557
    • Reist, E.J.1    Hart, P.A.2    Goodman, L.3    Baker, B.R.4
  • 18
    • 0009327401 scopus 로고
    • Purine nucleosides. V. Preparation and reactions of some 9β-D-ribofuranosyl-3′-5′-purine cyclonucleosides
    • Holmes, R.E.; Robins, R.K. Purine nucleosides. V. Preparation and reactions of some 9β-D-ribofuranosyl-3′-5′-purine cyclonucleosides. J. Org. Chem. 1963, 28, 3483.
    • (1963) J. Org. Chem. , vol.28 , pp. 3483
    • Holmes, R.E.1    Robins, R.K.2
  • 19
    • 25344468297 scopus 로고
    • 3,5′-cyclonucleosides in the reaction of xanthosine with dimethylformamide acetals
    • 3,5′-cyclonucleosides in the reaction of xanthosine with dimethylformamide acetals. Coll. Czech. Chem. Commun. 1968, 33, 3796.
    • (1968) Coll. Czech. Chem. Commun. , vol.33 , pp. 3796
    • Žemlička, J.1
  • 20
    • 84982373258 scopus 로고
    • Tertiary phosphane/tetrachloromethane, a versatile reagent for chlorination, dehydration, and P-N linkage
    • Appel, R. Tertiary phosphane/tetrachloromethane, a versatile reagent for chlorination, dehydration, and P-N linkage. Angew. Chem., Int. Ed. Engl. 1975, 14, 801.
    • (1975) Angew. Chem., Int. Ed. Engl. , vol.14 , pp. 801
    • Appel, R.1
  • 24
    • 0032776730 scopus 로고    scopus 로고
    • Syntheses of 5′- deoxy-5′-N-hydroxylaminopyrimidine and purine nucleosides: Building blocks for novel antisense oligonucleosides with hydroxamate linkages
    • Li, H.; Miller, M.J. Syntheses of 5′- deoxy-5′ -N-hydroxylaminopyrimidine and purine nucleosides: building blocks for novel antisense oligonucleosides with hydroxamate linkages. J. Org. Chem. 1999, 64, 9289.
    • (1999) J. Org. Chem. , vol.64 , pp. 9289
    • Li, H.1    Miller, M.J.2
  • 25
    • 0029123291 scopus 로고
    • Synthesis of 5′-O-amino-2′-deoxypyrimidine and purine nucleosides: Building-blocks for antisense oligonucleosides
    • Perbost, M.; Hoshiko, T.; Morvan, F.; Swayze, E.; Griffey, R.H.; Sanghvi, Y.S. Synthesis of 5′-O-amino-2′-deoxypyrimidine and purine nucleosides: building-blocks for antisense oligonucleosides. J. Org. Chem. 1995, 60, 5150.
    • (1995) J. Org. Chem. , vol.60 , pp. 5150
    • Perbost, M.1    Hoshiko, T.2    Morvan, F.3    Swayze, E.4    Griffey, R.H.5    Sanghvi, Y.S.6
  • 26
    • 0013791437 scopus 로고
    • Formycin B its relation to formycin
    • Koyama, G.; Umezawa, H. Formycin B and its relation to formycin. J. Antibiot. 1965, 18, 175.
    • (1965) J. Antibiot. , vol.18 , pp. 175
    • Koyama, G.1    Umezawa, H.2
  • 28
    • 0015882201 scopus 로고
    • Crystal structure and molecular conformation of formycin monohydrates. Possible origin of the anomalous circular dichroic spectra in formycin mono- and polynucleotides
    • Prusiner, P.; Brennan, T.; Sundaralingam, M. Crystal structure and molecular conformation of formycin monohydrates. Possible origin of the anomalous circular dichroic spectra in formycin mono- and polynucleotides. Biochemistry 1973, 12, 1196.
    • (1973) Biochemistry , vol.12 , pp. 1196
    • Prusiner, P.1    Brennan, T.2    Sundaralingam, M.3
  • 30
    • 0016168533 scopus 로고
    • Pyrazolopyrimidine nucleosides. V. Methylation of the C-nucleoside antibiotic formycin and structural elucidation of products by magnetic circular dichroism spectroscopy
    • Townsend, L.B.; Long, R.A.; McGraw, J.P.; Miles, D.W.; Robins, R.K.; Eyring, H. Pyrazolopyrimidine nucleosides. V. Methylation of the C-nucleoside antibiotic formycin and structural elucidation of products by magnetic circular dichroism spectroscopy. J. Org. Chem. 1974, 39, 2023.
    • (1974) J. Org. Chem. , vol.39 , pp. 2023
    • Townsend, L.B.1    Long, R.A.2    McGraw, J.P.3    Miles, D.W.4    Robins, R.K.5    Eyring, H.6
  • 31
    • 0016562173 scopus 로고
    • Formycin Anhydronucleosides. Conformation of formycin and conformational specificity of adenosine deaminase
    • Žemlička, J. Formycin Anhydronucleosides. Conformation of formycin and conformational specificity of adenosine deaminase. J. Am. Chem. Soc. 1975, 97, 5896.
    • (1975) J. Am. Chem. Soc. , vol.97 , pp. 5896
    • Žemlička, J.1
  • 32
    • 0016015448 scopus 로고
    • Molecular structure and conformation of the nucleoside antibiotic derivative 2-methylformycin with a C-glycosidic bond
    • Abola, J.E.; Sims, M.J.; Abraham, D.J. Molecular structure and conformation of the nucleoside antibiotic derivative 2-methylformycin with a C-glycosidic bond. J. Med. Chem. 1974, 17, 62.
    • (1974) J. Med. Chem. , vol.17 , pp. 62
    • Abola, J.E.1    Sims, M.J.2    Abraham, D.J.3
  • 33
    • 0027262226 scopus 로고
    • Nucleosides 5. Synthesis of guanine and formycin-B derivatives as potential inhibitors of purine nucleoside phosphorylase
    • Chern, J.-W.; Lee, H.-Y.; Chen, C.-S.; Shewach, D.S.; Daddona, P.E.; Townsend, L.B. Nucleosides 5. Synthesis of guanine and formycin-B derivatives as potential inhibitors of purine nucleoside phosphorylase. J. Med. Chem. 1993, 36, 1024.
    • (1993) J. Med. Chem. , vol.36 , pp. 1024
    • Chern, J.-W.1    Lee, H.-Y.2    Chen, C.-S.3    Shewach, D.S.4    Daddona, P.E.5    Townsend, L.B.6
  • 34
    • 0009323676 scopus 로고
    • Acyclic nucleoside analogues: Methods for the preparation of 2′,3′-secoguanosine, 5′-deoxy-2′,3′-secoguanosine, and (R,S)-9[1-(2-hydroxyethoxy)-2-hydroxyethyl]guanine
    • McGee, D.P.C.; Martin, J.C. Acyclic nucleoside analogues: methods for the preparation of 2′,3′-secoguanosine, 5′-deoxy-2′ ,3′-secoguanosine, and (R,S)-9[1-(2-hydroxyethoxy)-2-hydroxyethyl]guanine. Can. J. Chem. 1986, 64, 1885.
    • (1986) Can. J. Chem. , vol.64 , pp. 1885
    • McGee, D.P.C.1    Martin, J.C.2
  • 36
    • 0014082664 scopus 로고
    • Nucleotides. VII. Preparation and optical rotatory dispersion of some 8β-D-ribofuranosyl-2,5′-purine cyclonucleosides
    • Hampton, A.; Nichol, A.W. Nucleotides. VII. Preparation and optical rotatory dispersion of some 8β-D-ribofuranosyl-2,5′-purine cyclonucleosides. J. Org. Chem. 1967, 32, 1688.
    • (1967) J. Org. Chem. , vol.32 , pp. 1688
    • Hampton, A.1    Nichol, A.W.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.