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Volumn 28, Issue 10, 2009, Pages 969-986

Synthesis of 3'-amino-3'-deoxyguanosine and 3'-amino-3'-deoxyxyloguanosine monophosphate hepdirect prodrugs from guanosine

Author keywords

3' amino 3' deoxyguanosines; HepDirect prodrugs; NTPs

Indexed keywords

3' AMINO 3' DEOXYGUANOSINE; 3' AMINO 3' DEOXYXYLOGUANOSINE PHOSPHATE; 9 (2,5 BIS O TERT BUTYLDIMETHYLSILYL BETA DEXRO RIBOFURANOSYL) 2 N (N,N DIBENZYLFORMAMIDINO)GUANINE; 9 [3 AMINO 5 O [4 (3 CHLOROPHENYL) 1,3 DIOXA 2 OXOPHOSPHORINAN 2 YL] 3 DEOXY BETA DEXTRO RIBOFURANOSYL]GUANINE; 9 [3 AMINO 5 O [4 (3 CHLOROPHENYL) 1,3 DIOXA 2 OXOPHOSPHORINAN 2 YL] BETA DEXTRO XYLOFURANOSYL]GUANINE; GUANINE DERIVATIVE; GUANOSINE; GUANOSINE DERIVATIVE; METHANOL; NUCLEOSIDE TRIPHOSPHATE; PRODRUG; UNCLASSIFIED DRUG;

EID: 75149169870     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1080/15257770903307151     Document Type: Article
Times cited : (7)

References (58)
  • 2
    • 0000321149 scopus 로고
    • Puromycin. Synthetic studies. XV. 3-Amino-3-deoxyadenosine
    • Early synthesis work:
    • Early synthesis work: b) Baker, B.R.; Schaub, R.E.; Kissman, H.M. Puromycin. Synthetic studies. XV. 3-Amino-3-deoxyadenosine. J. Am. Chem. Soc. 1955, 77, 5911-5915;
    • (1955) J. Am. Chem. Soc. , vol.77 , pp. 5911-5915
    • Baker, B.R.1    Schaub, R.E.2    Kissman, H.M.3
  • 3
    • 2042447354 scopus 로고
    • Synthesis and reactions of 3-amino-3-deoxyribosides of 6-chloropurine
    • c) Goldman, L.; Marsico, J.W. Synthesis and reactions of 3-amino-3-deoxyribosides of 6-chloropurine. J. Med. Chem. 1963, 6, 413-423;
    • (1963) J. Med. Chem. , vol.6 , pp. 413-423
    • Goldman, L.1    Marsico, J.W.2
  • 4
    • 0014118744 scopus 로고
    • Some reactions of 9-(2,3-anhydro-5-deoxy-.beta.-D-pentofuranosyl)adenines
    • d) Reist, E.J.; Calkins, D.F.; Goodman, L. Some reactions of 9-(2,3-anhydro-5-deoxy-.beta.-D-pentofuranosyl)adenines. J. Org. Chem. 1967, 32, 2538-2541;
    • (1967) J. Org. Chem. , vol.32 , pp. 2538-2541
    • Reist, E.J.1    Calkins, D.F.2    Goodman, L.3
  • 5
    • 0016405823 scopus 로고
    • Nucleic acid related compounds. II. Adenosine 2-,3-ribo-epoxide. Synthesis, intramolecular degradation, and transformation into 3- Substituted xylofuranosyl nucleosides and the lyxo-epoxide
    • e) Robins, M.J.; Fouron, Y.; Mengel, R. Nucleic acid related compounds. II. Adenosine 2-,3-ribo-epoxide. Synthesis, intramolecular degradation, and transformation into 3- substituted xylofuranosyl nucleosides and the lyxo-epoxide. J. Org. Chem. 1974, 39, 1564-1570;
    • (1974) J. Org. Chem. , vol.39 , pp. 1564-1570
    • Robins, M.J.1    Fouron, Y.2    Mengel, R.3
  • 6
    • 0018718514 scopus 로고
    • 2-,3-Bis(2-chloroethyl)aminophosphoryl-3-amino-3-deoxyadenosine: A cyclic nucleotide with antitumor activity
    • f) Okruszek, A.; Verkade, J.G. 2-,3-Bis(2-chloroethyl)aminophosphoryl-3- amino-3-deoxyadenosine: a cyclic nucleotide with antitumor activity. J. Med. Chem. 1979, 22, 882-885;
    • (1979) J. Med. Chem. , vol.22 , pp. 882-885
    • Okruszek, A.1    Verkade, J.G.2
  • 7
    • 0029848266 scopus 로고    scopus 로고
    • Synthesis of purine and pyrimidine 3-amino-3- deoxy-and 3-amino-2-,3-dideoxyxylonucleosides
    • More recent synthesis work: g
    • More recent synthesis work: g) Garćia-Alles, L.F.; Magdalena, J.; Gotor, V. Synthesis of purine and pyrimidine 3-amino-3- deoxy- and 3-amino-2-,3-dideoxyxylonucleosides. J. Org. Chem. 1996, 61, 6980-6986;
    • (1996) J. Org. Chem. , vol.61 , pp. 6980-6986
    • Garćia-Alles, L.F.1    Magdalena, J.2    Gotor, V.3
  • 8
    • 0035977250 scopus 로고    scopus 로고
    • Syntheses of puromycin from adenosine and 7- deazapuromycin from tubercidin, and biological comparisons of the 7-aza/deaza pair
    • h) Robins, M.J.; Miles, R.W.; Samano, M.C.; Kaspar, R.L. Syntheses of puromycin from adenosine and 7- deazapuromycin from tubercidin, and biological comparisons of the 7-aza/deaza pair. J. Org. Chem. 2001, 66, 8204-8210;
    • (2001) J. Org. Chem. , vol.66 , pp. 8204-8210
    • Robins, M.J.1    Miles, R.W.2    Samano, M.C.3    Kaspar, R.L.4
  • 9
    • 0037424326 scopus 로고    scopus 로고
    • A Practical route to 3-amino-3-deoxyadenosine derivatives and puromycin analogues
    • i) Nguyen-Trung, N.Q.; Botta, O.; Terenzi, S.; Strazewski, P. A Practical route to 3-amino-3-deoxyadenosine derivatives and puromycin analogues. J. Org. Chem. 2003, 68, 2038-2041;
    • (2003) J. Org. Chem. , vol.68 , pp. 2038-2041
    • Nguyen-Trung, N.Q.1    Botta, O.2    Terenzi, S.3    Strazewski, P.4
  • 10
    • 0842308215 scopus 로고    scopus 로고
    • A new protecting group 3-,5-O-sulfinyl' for xylo-nucleosides. A simple and efficient synthesis of 3-amino-3-deoxyadenosine (a puromycin intermediate), 2,2-anhydro-pyrimidine nucleosides and 2-,3-anhydro-adenosine
    • j) Takatsuki, K.-I.; Yamamoto, M.; Ohgushi, S.; Kohmoto, S.; Kishikawa, K.; Yamashita, H. A new protecting group 3,5-O-sulfinyl' for xylo-nucleosides. A simple and efficient synthesis of 3-amino-3-deoxyadenosine (a puromycin intermediate), 2,2-anhydro-pyrimidine nucleosides and 2-,3-anhydro-adenosine. Tetrahedron Lett. 2004, 45, 137-140.
    • (2004) Tetrahedron Lett. , vol.45 , pp. 137-140
    • Takatsuki, K.-I.1    Yamamoto, M.2    Ohgushi, S.3    Kohmoto, S.4    Kishikawa, K.5    Yamashita, H.6
  • 12
    • 0036558477 scopus 로고    scopus 로고
    • Azidonucleosides: Synthesis, reactions, and biological properties
    • Tanmaya, P. Azidonucleosides: Synthesis, reactions, and biological properties. Chem Rev. 2002, 102, 1623-1667.
    • (2002) Chem Rev. , vol.102 , pp. 1623-1667
    • Tanmaya, P.1
  • 14
    • 0035935737 scopus 로고    scopus 로고
    • Neoceptor concept based on molecular complementarity in GPCRs: A mutant adenosine a3 receptor with selectively enhanced affinity for amine-modified nucleosides
    • b) Jacobson, K.A.; Gao, Z.-G.; Chen, A.; Barak, D.; Kim, S.-A.; Lee, K.; Link, A.; Van Rompaey, P.; van Calenbergh, S.; Liang, B.T. Neoceptor concept based on molecular complementarity in GPCRs: A mutant adenosine a3 receptor with selectively enhanced affinity for amine-modified nucleosides. J. Med. Chem. 2001, 44, 4125-4136;
    • (2001) J. Med. Chem. , vol.44 , pp. 4125-4136
    • Jacobson, K.A.1    Gao, Z.-G.2    Chen, A.3    Barak, D.4    Kim, S.-A.5    Lee, K.6    Link, A.7    Van Rompaey, P.8    Van Calenbergh, S.9    Liang, B.T.10
  • 16
    • 1842613561 scopus 로고    scopus 로고
    • A convenient and versatile synthesis of 2- (and 3-)- amino (and azido)-2- (and 3-)-deoxyadenosine as diverse synthetic precursors of cyclic adenosine diphosphate ribose (cADPR
    • Kim, B.-T.; Kim, S.-K.; Lee, S.-J.; Hwang, K.-J. A convenient and versatile synthesis of 2- (and 3-)- amino (and azido)-2- (and 3-)-deoxyadenosine as diverse synthetic precursors of cyclic adenosine diphosphate ribose (cADPR). Bull. Korean. Chem. Soc. 2004, 25, 243-248.
    • (2004) Bull. Korean. Chem. Soc. , vol.25 , pp. 243-248
    • Kim, B.-T.1    Kim, S.-K.2    Lee, S.-J.3    Hwang, K.-J.4
  • 17
    • 0021241185 scopus 로고
    • RNA polymerase. Synthesis and kinetic inhibition by 9-(3-azido-3- deoxy-?-D-xylofuranosyl) derivatives of 5-ATP and 5-GTP
    • a) Panka, D.; Dennis, D. RNA polymerase. Synthesis and kinetic inhibition by 9-(3-azido-3- deoxy-?-D-xylofuranosyl) derivatives of 5-ATP and 5-GTP. J. Biol. Chem. 1984, 259, 8384-8387;
    • (1984) J. Biol. Chem. , vol.259 , pp. 8384-8387
    • Panka, D.1    Dennis, D.2
  • 19
    • 29244465548 scopus 로고    scopus 로고
    • Synthesis and anti-HIV activity of beta-D-3-azido-2-,3-unsaturated nucleosides and beta-D- 3-azido-3-deoxyribofuranosylnucleosides
    • c) Gadthula, S.; Chu, C.K. Synthesis and anti-HIV activity of beta-D-3-azido-2-,3-unsaturated nucleosides and beta-D- 3-azido-3- deoxyribofuranosylnucleosides. Nucleosides Nucleotides Nucleic Acids 2005, 24, 1707-1727.
    • (2005) Nucleosides Nucleotides Nucleic Acids , vol.24 , pp. 1707-1727
    • Gadthula, S.1    Chu, C.K.2
  • 20
    • 2042513212 scopus 로고
    • Analogs of the aminonucleoside derived from puromycin. The synthesis of 3-amino-3-deoxyguanosine and 3-amino-3-deoxycrotonoside
    • a) Kissman, H.M.; Hoffman, A.S.; Weiss, M.J. Analogs of the aminonucleoside derived from puromycin. The synthesis of 3-amino-3- deoxyguanosine and 3-amino-3-deoxycrotonoside. J. Med. Chem 1963, 6, 407-409;
    • (1963) J. Med. Chem , vol.6 , pp. 407-409
    • Kissman, H.M.1    Hoffman, A.S.2    Weiss, M.J.3
  • 21
    • 36849061578 scopus 로고    scopus 로고
    • Telomere shortening in human HL60 cells by treatment with 3-azido-2-,3-dideoxynucleosides and telomerase inhibition by their 5-triphosphates
    • b) Liu, X.; Inomata, M.; Ogawara, T.; Saneyoshi, M.; Yamaguchi, T. Telomere shortening in human HL60 cells by treatment with 3-azido-2-,3- dideoxynucleosides and telomerase inhibition by their 5-triphosphates. Nucleosides Nucleotides Nucleic Acids 2007, 26, 1067-1071.
    • (2007) Nucleosides Nucleotides Nucleic Acids , vol.26 , pp. 1067-1071
    • Liu, X.1    Inomata, M.2    Ogawara, T.3    Saneyoshi, M.4    Yamaguchi, T.5
  • 22
    • 0037254310 scopus 로고    scopus 로고
    • An efficient synthesis of 3-amino-3-deoxyguanosine from guanosine
    • Zhang, L.; Cui, Z.; Zhang, B. An efficient synthesis of 3-amino-3-deoxyguanosine from guanosine. Helv. Chim. Acta 2003, 86, 703-710.
    • (2003) Helv. Chim. Acta , vol.86 , pp. 703-710
    • Zhang, L.1    Cui, Z.2    Zhang, B.3
  • 24
    • 0030745066 scopus 로고    scopus 로고
    • Synthesis and application of 3- Amino-dye-terminators for DNA sequencing
    • b) Wojczewski, C.; Faulstich, K.; Engels, J.W. Synthesis and application of 3- amino-dye-terminators for DNA sequencing. Nucleosides Nucleotides 1997, 16, 751-754;
    • (1997) Nucleosides Nucleotides , vol.16 , pp. 751-754
    • Wojczewski, C.1    Faulstich, K.2    Engels, J.W.3
  • 25
    • 34547936757 scopus 로고    scopus 로고
    • Syntheses of (2-)3-15N-amino-(2-)3-deoxyguanosine and determination of their pKa Values by 15N NMR spectroscopy
    • c) Dai, Q.; Lea, C.R.; Lu, J.; Piccirilli, J.A. Syntheses of (2-)3- -15N-amino-(2-)3-deoxyguanosine and determination of their pKa Values by 15N NMR spectroscopy. Org. Lett. 2007, 9, 3057-3060.
    • (2007) Org. Lett. , vol.9 , pp. 3057-3060
    • Dai, Q.1    Lea, C.R.2    Lu, J.3    Piccirilli, J.A.4
  • 26
    • 75149163542 scopus 로고    scopus 로고
    • Methods and compositions using modified nucleosides for treating flaviviruses and pestiviruses
    • Inhibition of RNA dependent RNA polymerase (RdRp) has been targeted for treatment of HCV infection. Comparison of ribose-modified NTPs with natural bases as RdRp inhibitors: a
    • Inhibition of RNA dependent RNA polymerase (RdRp) has been targeted for treatment of HCV infection. Comparison of ribose-modified NTPs with natural bases as RdRp inhibitors: a) Sommadossi, J.P.; La Colla, P. Methods and compositions using modified nucleosides for treating flaviviruses and pestiviruses. WO 2001092282;
    • WO 2001092282
    • Sommadossi, J.P.1    La Colla, P.2
  • 31
    • 33748942512 scopus 로고    scopus 로고
    • Synthesis of 2-C-methylcytidine and 2-C-methyluridine derivatives modified in the 3-position as potential antiviral agents
    • f) Pierra, C.; Amador, A.; Badaroux, E.; Storer, R.; Gosselin, G. Synthesis of 2-C-methylcytidine and 2-C-methyluridine derivatives modified in the 3-position as potential antiviral agents. Collect. Czech. Chem. Commun. 2006, 71, 991-1010.
    • (2006) Collect. Czech. Chem. Commun. , vol.71 , pp. 991-1010
    • Pierra, C.1    Amador, A.2    Badaroux, E.3    Storer, R.4    Gosselin, G.5
  • 33
    • 0000335222 scopus 로고
    • AIDS-driven nucleoside chemistry
    • a) Huryn, D.M.; Okabe, M. AIDS-driven nucleoside chemistry. Chem. Rev. 1992, 92, 1745-1768;
    • (1992) Chem. Rev. , vol.92 , pp. 1745-1768
    • Huryn, D.M.1    Okabe, M.2
  • 34
    • 0032823876 scopus 로고    scopus 로고
    • Development and optimization of anti-HIV nucleoside analogs and prodrugs: A review of their cellular pharmacology, structure-activity relationships and pharmacokinetics
    • b) Tan, X.T.; Chu, C.K.; Boudinot, F.D. Development and optimization of anti-HIV nucleoside analogs and prodrugs: A review of their cellular pharmacology, structure-activity relationships and pharmacokinetics. Adv. Drug Delivery Rev. 1999, 39, 117-151.
    • (1999) Adv. Drug Delivery Rev. , vol.39 , pp. 117-151
    • Tan, X.T.1    Chu, C.K.2    Boudinot, F.D.3
  • 35
    • 11144357250 scopus 로고    scopus 로고
    • Design, Synthesis, and Characterization of a Series of Cytochrome P450 3A-activated prodrugs (HepDirect prodrugs) useful for targeting phosph(on)atebased drugs to the liver
    • Phosphate/phosphonate prodrug review:
    • a) Erion, M.D.; Reddy, K.R.; Boyer, S.H.; Matelich, M.C., Gomez-Galeno, J.; Lemus, R.H.; Ugarkar, B.G.; Colby, T.J.; Schanzer, J.; van Poelje, P.D. Design, Synthesis, and Characterization of a Series of Cytochrome P450 3A-activated prodrugs (HepDirect prodrugs) useful for targeting phosph(on)atebased drugs to the liver. J. Am. Chem. Soc. 2004, 126, 5154-5163. Phosphate/phosphonate prodrug review:
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 5154-5163
    • Erion, M.D.1    Reddy, K.R.2    Boyer, S.H.3    Matelich, M.C.4    Gomez-Galeno, J.5    Lemus, R.H.6    Ugarkar, B.G.7    Colby, T.J.8    Schanzer, J.9    Van Poelje, P.D.10
  • 36
    • 43049112098 scopus 로고    scopus 로고
    • Prodrugs of phosphates and phosphonates
    • Compounds in clinical trials with the HepDirect prodrug moiety: pradefovir:
    • b) Hecker, S.J.; Erion, M.D. Prodrugs of Phosphates and Phosphonates. J. Med. Chem. 2008, 51, 2328-2345. Compounds in clinical trials with the HepDirect prodrug moiety: pradefovir:
    • (2008) J. Med. Chem. , vol.51 , pp. 2328-2345
    • Hecker, S.J.1    Erion, M.D.2
  • 37
    • 10644269922 scopus 로고    scopus 로고
    • Remofovir mesylate: A prodrug of PMEA with improved liver-targeting and safety in rats and monkeys
    • c) Lin, C.-C.; Yeh, L.-T.; Vitarella, D.; Hong, Z.; Erion, M.D. Remofovir mesylate: A prodrug of PMEA with improved liver-targeting and safety in rats and monkeys. Antiviral Chem. Chemother. 2004, 15, 307-316;
    • (2004) Antiviral Chem. Chemother. , vol.15 , pp. 307-316
    • Lin, C.-C.1    Yeh, L.-T.2    Vitarella, D.3    Hong, Z.4    Erion, M.D.5
  • 40
    • 33845953970 scopus 로고    scopus 로고
    • Synthesis and characterization of a novel liver-targeted prodrug of cytosine-1-?-d-arabinofuranoside monophosphate for the treatment of hepatocellular carcinoma
    • MB07811
    • f) Boyer, S.H.; Sun, Z.; Jiang, H.; Esterbrook, J.; Gomez-Galeno, J.E.; Craigo, W.; Reddy, K.R.; Ugarkar, B.G.; MacKenna, D.A.; Erion, M.D. Synthesis and characterization of a novel liver-targeted prodrug of cytosine-1-?-d- arabinofuranoside monophosphate for the treatment of hepatocellular carcinoma. J. Med. Chem. 2006, 49, 7711-7720; MB07811;
    • (2006) J. Med. Chem. , vol.49 , pp. 7711-7720
    • Boyer, S.H.1    Sun, Z.2    Jiang, H.3    Esterbrook, J.4    Gomez-Galeno, J.E.5    Craigo, W.6    Reddy, K.R.7    Ugarkar, B.G.8    MacKenna, D.A.9    Erion, M.D.10
  • 44
    • 0000298078 scopus 로고    scopus 로고
    • Synthesis of enzymatically stable analogues of gdp for binding studies with transducin, the g-protein of the visual photoreceptor
    • Vincent, S.; Grenier, S.; Valleix, A.; Salesse, C.; Lebeau, L.; Mioskowski, C. Synthesis of enzymatically stable analogues of gdp for binding studies with transducin, the g-protein of the visual photoreceptor. J. Org. Chem. 1998, 63, 7244-7257.
    • (1998) J. Org. Chem. , vol.63 , pp. 7244-7257
    • Vincent, S.1    Grenier, S.2    Valleix, A.3    Salesse, C.4    Lebeau, L.5    Mioskowski, C.6
  • 45
    • 0001756111 scopus 로고
    • The synthesis of oligoribonucleotides. II. The use of silyl protecting groups in nucleoside and nucleotide chemistry. VII
    • a) Ogilvie, K.K.; Beaucage, S.L.; Schifman, A.L.; Theriault, N.Y.; Sadana, K.L. The synthesis of oligoribonucleotides. II. The use of silyl protecting groups in nucleoside and nucleotide chemistry. VII. Can. J. Chem. 1978, 56, 2768-2780;
    • (1978) Can. J. Chem. , vol.56 , pp. 2768-2780
    • Ogilvie, K.K.1    Beaucage, S.L.2    Schifman, A.L.3    Theriault, N.Y.4    Sadana, K.L.5
  • 46
    • 0000491298 scopus 로고
    • The synthesis of oligoribonucleotides. III. The use of silyl protecting groups in nucleoside and nucleotide chemistry. VIII
    • b) Ogilvie, K.K.; Schifman, A.L.; Penney, C.L. The synthesis of oligoribonucleotides. III. The use of silyl protecting groups in nucleoside and nucleotide chemistry. VIII. Can. J. Chem. 1979, 57, 2230-2238.;
    • (1979) Can. J. Chem. , vol.57 , pp. 2230-2238
    • Ogilvie, K.K.1    Schifman, A.L.2    Penney, C.L.3
  • 47
    • 0000168697 scopus 로고
    • New catalysts and procedures for the dimethoxytritylation and selective silylation of ribonucleosides
    • c) Hakimelahi, G.H.; Proba, Z.A.; Ogilvie, K.K. New catalysts and procedures for the dimethoxytritylation and selective silylation of ribonucleosides. Can. J. Chem. 1982, 60, 1106-1113.
    • (1982) Can. J. Chem. , vol.60 , pp. 1106-1113
    • Hakimelahi, G.H.1    Proba, Z.A.2    Ogilvie, K.K.3
  • 48
    • 49049148140 scopus 로고
    • Silyl protecting groups in nucleoside and nucleotide chemistry. Part XV. Isomerization of tert-butyldimethylsilyl protecting groups in ribonucleosides
    • Ogilvie, K.K.; Entwistle, D.W. Silyl protecting groups in nucleoside and nucleotide chemistry. Part XV. Isomerization of tert-butyldimethylsilyl protecting groups in ribonucleosides. Carbohydr. Res. 1981, 89, 203-210.
    • (1981) Carbohydr. Res. , vol.89 , pp. 203-210
    • Ogilvie, K.K.1    Entwistle, D.W.2
  • 49
    • 0024549220 scopus 로고
    • Synthesis of 9-(3-azido-2,3-dideoxy-?-D-erythro-pentofuranosyl)- 2,6-diaminopurine (AzddDAP
    • a) Herdewijn, P.; Van Aerschot, A. synthesis of 9-(3-azido-2,3-dideoxy-?- D-erythro-pentofuranosyl)- 2,6-diaminopurine (AzddDAP). Tetrahedron Lett. 1989, 30, 855-858;
    • (1989) Tetrahedron Lett. , vol.30 , pp. 855-858
    • Herdewijn, P.1    Van Aerschot, A.2
  • 50
    • 0026599971 scopus 로고
    • Nucleic acid related compounds. 71. Efficient general syntheis of purine (amino. azido, and triflate)-sugar nucleosides
    • b) Robins, M.J.; Hawrelak, S.D.; Hernandez, A.E.; Wnuk, S.F. Nucleic acid related compounds. 71. Efficient general syntheis of purine (amino. azido, and triflate)-sugar nucleosides. Nucleosides Nucleotides 1992, 11, 821-834;
    • (1992) Nucleosides Nucleotides , vol.11 , pp. 821-834
    • Robins, M.J.1    Hawrelak, S.D.2    Hernandez, A.E.3    Wnuk, S.F.4
  • 52
    • 0024359262 scopus 로고
    • Nucleic acid related compounds. 57. Synthesis, x-ray crystal structure, lipophilic partition properties, and antiretroviral activities of anomeric 3-azido-2-,3-dideoxy-2,6-diaminopurine ribosides
    • Robins, M.J.; Wood, S.G.; Dalley, N.K.; Herdewijn, P.; Balzarini, J.; De Clercq, E. Nucleic acid related compounds. 57. Synthesis, x-ray crystal structure, lipophilic partition properties, and antiretroviral activities of anomeric 3-azido-2-,3-dideoxy-2,6-diaminopurine ribosides. J. Med. Chem. 1989, 32, 1763-1768.
    • (1989) J. Med. Chem. , vol.32 , pp. 1763-1768
    • Robins, M.J.1    Wood, S.G.2    Dalley, N.K.3    Herdewijn, P.4    Balzarini, J.5    De Clercq, E.6
  • 53
    • 75149196962 scopus 로고    scopus 로고
    • The alcohol 7 was unreactive to methanesulfonylchloride and use of trifluoromethanesulfonylchloride only produced complex mixtures
    • The alcohol 7 was unreactive to methanesulfonylchloride and use of trifluoromethanesulfonylchloride only produced complex mixtures.
  • 54
    • 19444368441 scopus 로고    scopus 로고
    • Stereoselective synthesis of nucleoside monophosphate HepDirect prodrugs
    • The phosphorinane reagent (11) is a 1:1 C4-R/S-diastereomeric mixture. The reagent 11 and adducts are represented as C4-R-isomers for convenience. Thus, 1H NMR of certain proton resonances (e.g., TBS methyl shifts) in the product 12 as well as some other subsequent compounds display twinning of peaks. For more details on this reaction see also
    • The phosphorinane reagent (11) is a 1:1 C4-R/S-diastereomeric mixture. The reagent 11 and adducts are represented as C4-R-isomers for convenience. Thus, 1H NMR of certain proton resonances (e.g., TBS methyl shifts) in the product 12 as well as some other subsequent compounds display twinning of peaks. For more details on this reaction see also Reddy, K.R.; Boyer, S.H.; Erion, M.D. Stereoselective synthesis of nucleoside monophosphate HepDirect prodrugs. Tetrahedron Lett. 2005, 46, 4321-4324.
    • (2005) Tetrahedron Lett. , vol.46 , pp. 4321-4324
    • Reddy, K.R.1    Boyer, S.H.2    Erion, M.D.3
  • 55
    • 0000596962 scopus 로고
    • Nucleotide chemistry. XX. Use of the azido group in the synthesis of 5-terminal aminodeoxythymidine oligonucleotides
    • Mungall, W.S.; Greene, G.L.; Heavner, G.A.; Letsinger, R.L. Nucleotide chemistry. XX. Use of the azido group in the synthesis of 5-terminal aminodeoxythymidine oligonucleotides. J. Org. Chem. 1975, 40, 1659-1662.
    • (1975) J. Org. Chem. , vol.40 , pp. 1659-1662
    • Mungall, W.S.1    Greene, G.L.2    Heavner, G.A.3    Letsinger, R.L.4
  • 57
    • 0028243449 scopus 로고
    • Synthesis and conformational analysis of 2-deoxy- 2-(3-methoxybenzamido) adenosine, a rational-designed inhibitor of trypanosomal glyceraldehyde phosphate dehydrogenase (GAPDH
    • a) Van Calenbergh, S.; Van Den Eeckhout, E.; Herdewijn, P.; De Bruyn, A.; Verlinde, C.; Hol, W.; Callens, M.; Van Aerschot, A.; Rozenski, J. Synthesis and conformational analysis of 2-deoxy- 2-(3-methoxybenzamido)adenosine, a rational-designed inhibitor of trypanosomal glyceraldehyde phosphate dehydrogenase (GAPDH). Helv. Chim. Acta 1994, 77, 631-644;
    • (1994) Helv. Chim. Acta , vol.77 , pp. 631-644
    • Van Calenbergh, S.1    Van Den Eeckhout, E.2    Herdewijn, P.3    De Bruyn, A.4    Verlinde, C.5    Hol, W.6    Callens, M.7    Van Aerschot, A.8    Rozenski, J.9
  • 58
    • 0034263911 scopus 로고    scopus 로고
    • Polymer-assisted solution-phase synthesis of 2-amido- 2-deoxyadenosine derivatives targeted at the NAD+-binding sites of parasite enzymes
    • b) Golisade, A.; Bressi, J.C.; Van Calenbergh, S.; Gelb, M.H.; Link, A. Polymer-assisted solution-phase synthesis of 2-amido- 2-deoxyadenosine derivatives targeted at the NAD+-binding sites of parasite enzymes. J. Comb. Chem. 2000, 2, 537-544.
    • (2000) J. Comb. Chem. , vol.2 , pp. 537-544
    • Golisade, A.1    Bressi, J.C.2    Van Calenbergh, S.3    Gelb, M.H.4    Link, A.5


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