Synthesis and Studies of 3′-C-Trifluoromethyl-β -D-ribonucleosides Bearing the Five Naturally Occurring Nucleic Acid Bases

Nucleosides, Nucleotides and Nucleic Acids

Volumn 22, Issue 12, 2003, Pages 2195-2202

  Jeannot, Frédéric ^a   Gosselin, Gilles ^a,b   Mathé, Christophe ^a  

^a UNIVERSITÉ DE MONTPELLIER   (France)

^b CNRS   (France)

Author keywords

3 C Trifluoromethyl D ribonucleosides; Antiviral agents

Indexed keywords

3' TRIFLUOROMETHYL BETA DEXTRO RIBONUCLEOSIDE; NUCLEIC ACID BASE; PURINE; PYRIMIDINE; RIBONUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; DRUG MECHANISM; DRUG SCREENING; DRUG SYNTHESIS; GLYCOSYLATION; HEPATITIS B VIRUS; HUMAN IMMUNODEFICIENCY VIRUS; NONHUMAN; RNA VIRUS; VIRUS REPLICATION;

ANTIVIRAL AGENTS; FLUORINE; GLYCOSYLATION; HEPATITIS B VIRUS; HIV; HUMANS; MICROBIAL SENSITIVITY TESTS; PURINES; PYRIMIDINES; RIBONUCLEOSIDES; RNA VIRUSES;

HEPATITIS B VIRUS; HUMAN IMMUNODEFICIENCY VIRUS; RNA VIRUSES;

EID: 0346850792     PISSN: 15257770     EISSN: None     Source Type: Journal    
DOI: 10.1081/NCN-120026874     Document Type: Article

References (8)

1. De Clercq, E. Strategies in the design of antiviral drugs. Nat. Rev. Drug Discovery 2002, 1, 13-25.
2. Salvetti, R.; Marchand, A.; Pregnolato, M.; Verri, A.; Spadari, S.; Focher, F.; Bryant, M.; Sommadossi, J.P.; Mathé, C.; Gosselin, G. 5-(Trifluoromethyl)-beta-L-2′-deoxyuridine, the L-enantiomer of trifluorothymidine: Stereospecific synthesis and antiherpetic evaluations. Bioorg. Med. Chem. 2001, 9, 1731-1738.
3. Jeannot, F.; Gosselin, G.; Standring, D.; Bryant, M.; Sommadossi, J.P.; Loi, A. G.; La Colla, P.; Mathé, C. Synthesis and studies of 3′-C-trifluoromethyl nucleoside analogues bearing adenine or cytosine as the base. Bioorg. Med. Chem. 2002, 10, 3153-3161.
4. Jeannot, F.; Mathé, C.; Gosselin, G. Synthesis and antiviral evaluation of 3′-C-trifluoromethyl nucleoside derivatives bearing adenine as the base. Nucleosides, Nucleotides, Nucleic Acids 2001, 20, 755-758.
5. Jeannot, F.; Gosselin, G.; Mathé, C. Synthesis and antiviral evaluation of 2′-deoxy-2′-C-trifluoromethyl β-D-ribonucleoside analogues bearing the five naturally occurring nucleic acid bases. Org. Biomol. Chem. 2003, 1, 2096-2102.
6. Johnson, C.R.; Bhumralkar, D.R.; De Clercq, E. 3′ -C-Trifluoromethyl ribonucleosides. Nucleosides, Nucleotides 1995, 14, 185-194.
7. Lee, W.L.; Martinez, A.P.; Goodman, L.; Henry, D.W. Guanine, thioguanine, and related nucleosides by the mercuric cyanide-silyl method. An improved synthesis of α-2′-deoxythioguanosine. J. Org. Chem. 1972, 37, 2923-2927.
8. Legorburu, U.; Reese, C.B.; Song, Q. Conversion of uridine into 2′-O-(2-methoxyethyl)uridine and 2′-O-(methoxyethyl)cytidine. Tetrahedron 1999, 55, 5635-5640.