Synthesis of triazole nucleoside derivatives

Nucleosides, Nucleotides and Nucleic Acids

Volumn 22, Issue 4, 2003, Pages 419-435

  Li, Zicheng ^a   Chen, Shuhua ^a   Jiang, Ning ^b   Cui, Gang ^a  

^a SICHUAN UNIVERSITY   (China)

^b Sichuan Industrial Institute of Antibiotics   (China)

Author keywords

Antiviral activity; Ribavirin derivative; Synthesis; Triazole nucleoside derivative

Indexed keywords

1 [2 O ACETYL 3 BROMO 3 DEOXY 5 O (2,5,5 TRIMETHYL 1,3 DIOXOLAN 4 ON 2 YL) BETA DEXTRO XYLOFURANOSYL] 1,2,4 TRIAZOLE 3 CARBOXAMIDE; 2 ACETOXYISOBUTYRYL BROMIDE; 2 ACETOXYISOBUTYRYL CHLORIDE; 2',3' O ISOPROPYLIDENE RIBONUCLEOSIDE DERIVATIVE; 5' O MESYL 2',3' O ISOPROPYLIDENE RIBONUCLEOSIDE DERIVATIVE; ACETAL DERIVATIVE; ACETONE DIETHYL ACETAL; ANTINEOPLASTIC AGENT; ANTIVIRUS AGENT; BROMINE; CHLORIDE; COPPER; HALIDE; NUCLEOSIDE; NUCLEOSIDE DERIVATIVE; SODIUM BROMIDE; SODIUM NITRITE; TRIAZOLE DERIVATIVE; TRIAZOLE NUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG; ZINC;

ANIMAL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL; CHEMICAL REACTION; CHEMISTRY; DRUG ACTIVITY; DRUG SYNTHESIS; HUMAN; HYDROGENATION; LIVER CARCINOMA; LUNG CARCINOMA; SYNTHESIS; TUMOR CELL LINE;

ANIMALS; ANTINEOPLASTIC AGENTS; ANTIVIRAL AGENTS; CELL LINE, TUMOR; HUMANS; NUCLEOSIDES; TRIAZOLES;

ANIMALIA;

EID: 0037773497     PISSN: 15257770     EISSN: None     Source Type: Journal    
DOI: 10.1081/NCN-120022032     Document Type: Article

References (10)

1. Witkowski, J.T.; Robins, R.K.; Sidwell, R.W.; Simon, L.N. Design, synthesis, and broad spectrum antiviral activity of 1-β-D-ribofuranosyl-1,2,4-triazole-3-carboxamide and related nucleosides. J. Med. Chem. 1972, 15 (11), 1150-1154.
2. AIDU. Drugs of the future 1982, 7 (6), 375-377.
3. Hampton, A. Nucleosides. II. A new prepareation for the conversion of ribonucleosides to 2′,3′-O-isopropylidene derivatives. J. Chem. Soc. 1961, 83, 3640-3645.
4. Jain, T.C.; Jenkins, I.D.; Russell, A.F.; Verheyden, J.P.H.; Moffatt, J.G. Reactions of 2-acyloxyisobutyryl halides with nucleosides. IV. A facile synthesis of 2′,3′-unsaturated nucleosides using chromous acetate. J. Org. Chem. 1974, 39 (1), 30-38.
5. Greenberg, S.; Moffatt, J.G. Reactions of 2-acyloxyisobutyryl halides with nucleosides. I. Reactions of model diols and of uridine. J. Am. Chem. Soc. 1973, 95 (12), 4016-4025.
6. Mattocks, A.R. Novel reactions of some α-acyloxy-acid halides. Part II. Some further examples. J. Chem. Soc. 1964, 4840-4845.
7. Russell, A.F.; Greenberg, S.; Moffatt, J.G. Reactions of 2-acyloxyisobutyryl halides with nucleosides. II. Reactions of adenosine. J. Am. Chem. Soc. 1973, 95 (12), 4025-4030.
8. Bhat, V.; Stocker, E.; Ugarkar, B.G. A new synthesis of 2′,3′-dideoxyinosine. Synth. Commun. 1992, 22 (10), 1481-1486.
9. Mansuri, M.M.; Starrett, J.E.; Wos, J.A., Jr.; Tortolani, D.R.; Brodfuehrer, P.R.; Howell, H.G.; Martin, J.C. Preparation of 1-(2,3-dideoxy-β-D-glyceropent-2-enofuranosyl)thymine (d4T) and 2′,3′-dideoxyadenosine (ddA): General methods for the synthesis of 2′,3′-olefinic and 2′,3′-dideoxy nucleoside anaolues active against HIV. J. Org. Chem. 1989, 54, 4780-4785.
10. Witkowski, J.T.; Robins, R.K. The chemical synthesis of the 1,2,4-triazole nucleosides related to uridine, 2′-deoxyuridine, thymidine, and cytidine. J. Org. Chem. 1970, 35 (8), 2635-2641.