Synthesis and antiviral evaluation of D4T analogues with a spacer arm between glucidic and base moieties

Nucleosides, Nucleotides and Nucleic Acids

Volumn 23, Issue 10, 2004, Pages 1625-1637

  Roy, Vincent ^a   Zerrouki, Rachida ^a   Krausz, Pierre ^a   Schmidt, Sylvie ^b   Aubertin, Anne Marie ^b  

^a UNIVERSITY OF LIMOGES   (France)

^b INSERM   (France)

Author keywords

Glycosylation; HIV; Microwave; Nucleosides; Selective deprotection

Indexed keywords

1 [2 (2',3' DIDEHYDRO 2',3' DIDEOXY BETA DEXTRO RIBOFURANOSYLOXY)ETHYL]THYMINE; 1 [3 (2',3' DIDEHYDRO 2',3' DIDEOXY BETA DEXTRO RIBOFURANOSYLOXY)PROPYL]THYMINE; 1 [4 (2',3' DIDEHYDRO 2',3' DIDEOXY BETA DEXTRO RIBOFURANOSYLOXY)BUTYL]THYMINE; ANTIVIRUS AGENT; CARBOHYDRATE DERIVATIVE; STAVUDINE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; BASE PAIRING; DRUG SYNTHESIS; GLYCOSYLATION; HUMAN IMMUNODEFICIENCY VIRUS 1; INFRARED SPECTROSCOPY; MICROWAVE IRRADIATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

CELL LINE; HIV-1; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; REVERSE TRANSCRIPTASE INHIBITORS; SPECTROPHOTOMETRY, INFRARED; STAVUDINE;

HUMAN IMMUNODEFICIENCY VIRUS; HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 9644254200     PISSN: 15257770     EISSN: None     Source Type: Journal    
DOI: 10.1081/NCN-200031457     Document Type: Article

References (16)

1. Dodin, G.; Kühnel, S.M.; Demersman, P.; Kotzyba, J. The linking chain length in bridged aldehyde-substituted pyridinium dimers modulates a slow reversible binding that affects supercoiling of plasmid DNA. Anticancer Drug Des. 1993, 8 (5), 361-368.
2. 2 linkage. Bioorg. Med. Chem. Lett. 1994, 4 (12), 1497-1500.
3. Sagi, J.; Smezo, A.; Ebinger, K.; Szabolcs, A.; Sagi, G.; Ruff, E.; Otvos, L. Base-modified oligodeoxynucleotides. I. Effect of 5-alkyl, 5-(1-alkenyl) and 5-(1-alkynyl) substitution of the pyrimidines on duplex stability and hydrophobicity. Tetrahedron Lett. 1993, 34 (13), 2191-2194.
4. Cruickshank, K.A.; Jiricny, J.; Reese, C.B. The benzoylation of uracil and thymine. Tetrahedron Lett. 1984, 25 (6), 681-684.
5. Browne, D.T.; Eisingerand, F.J.; Leonard, N.J. Synthetic spectroscopic models related to coenzymes and base pairs. II. Evidence for intramolecular base-base interactions in dinucleotide analogs. J. Am. Chem. Soc. 1968, 90 (26), 7302-7323.
6. Sazaki, T.; Minamoto, V.; Susuki, T.; Yamashita, S. Search for a simpler synthetic model system for intramolecular 1,3-dipolar cycloaddition to the 5,6-double bond of a pyrimidine nucleoside. Tetrahedron 1980, 36 (7), 865-870.
7. Adbel-Megied, A.E.S.; Motawia, M.S.; Pedersen, E.B.; Nielsen, C.M. 5-Alkoxy-methyl-1-hydroxyalkyluracils with potential anti-HIV activity. Heterocycles 1992, 34 (4), 713-722.
8. Grandjean, P.; Benhaddou, R.; Granet, R.; Krausz, P. A unexpected result in the alkylation of thymine. Tetrahedron Lett. 1997, 38 (35), 6185-6188.
9. Perreux, L.; Loupy, A. A tentative rationalization of microwave effects in organic synthesis according to the reaction medium, and mechanistic considerations. Tetrahedron 2001, 57 (45), 9199-9223.
10. Limousin, C.; Cléophax, J.; Petit, A.; Loupy, A.; Lukacs, G. Solvent-free synthesis of decyl D-glycopyranosides under focused microwave irradiation. J. Carbohydr. Chem. 1997, 16 (3), 327-342.
11. Hannessian, S.; Banoub, J. Preparation of 1,2-trans-glycosides in the presence of stannic chloride. Methods Carbohydr. Chem. 1980, 8, 243-245.
12. Chu, C.K.; Bhadti, V.S.; Doboszewski, B. General syntheses of 2′,3′-dideoxynucleosides and 2′,3′-didehydro-2′, 3′-dideoxynucleosides. J. Org. Chem. 1989, 54 (9), 2217-2225.
13. Corey, E.J.; Hopkins, P.B. A mild procedure for the conversion of 1,2-diols to olefins. Tetrahedron Lett. 1982, 23 (19), 1979-1982.
14. Moog, C.; Wick, A.; Le Ber, P.; Kirn, A.; Aubertin, A.M. Bicyclic imidazo derivatives, a new class of highly selective inhibitors for the human immunodeficiency virus type I. Antivir. Res. 1994, 24 (4), 275-288.
15. Mossman, T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods 1983, 65, 55-63.
16. 50, synergism, antagonism, low-dose risk, receptor binding and enzyme kinetics. In Computer Software Apple II Series and IBM-PC and Instruction Manual; Elsevier-Biosoft, Elsevier Science Publishers: Cambridge, UK, 1985; 19-28.