Regioselective Synthesis of Indazole N1- and N 2-(β-D-Ribonucleosides)

Nucleosides, Nucleotides and Nucleic Acids

Volumn 23, Issue 1-2, 2004, Pages 227-237

  Seela, Frank ^a   Peng, Xiaohua ^a  

^a UNIVERSITY OF OSNABRÜCK   (Germany)

Author keywords

4 Nitroindazole; Fluorescence; Glycosylation; Regioselectivity; Ribonucleosides

Indexed keywords

4 NITRO 1 (BETA DEXTRO RIBOFURANOSYL) 1H INDAZOLE; 4 NITRO 1 [(2,3,5 TRI O BENZOYL) BETA DEXTRO RIBOFURANOSYL] 1H INDAZOLE; 4 NITRO 2 (BETA DEXTRO RIBOFURANOSYL) 2H INDAZOLE; 4 NITRO 2 [(2,3,5 TRI O BENZOYL) BETA DEXTRO RIBOFURANOSYL] 2H INDAZOLE; INDAZOLE DERIVATIVE; RIBONUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; FLUORESCENCE; GLYCOSYLATION; HYDROGENATION; ISOMER; KINETICS; STEREOCHEMISTRY; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY;

GLYCOSYLATION; INDAZOLES; MAGNETIC RESONANCE SPECTROSCOPY; RIBONUCLEOSIDES;

EID: 1242318650     PISSN: 15257770     EISSN: None     Source Type: Journal    
DOI: 10.1081/NCN-120027830     Document Type: Article

References (23)

1. C, 92 pp.
2. C, 197 pp.
3. Gatta, F.; Luciani, M.; Palazzo, G. Pyrazolo[3,4-d]pyrimidines related to lonidamine. J. Heterocycl. Chem. 1989, 26, 613-618.
4. Beyer, B.; Raga, A.C.; Urbina, C.; Hurtado, I. Antiallergic activity of some indazole derivatives. Acta Cient. Venez. 1984, 35 (2), 103-106.
5. 3 receptor. J. Med. Chem. 1987, 30 (9), 1535-1537.
6. Revankar, G.R.; Townsend, L.B. The synthesis of certain ribofuranosylindazoles (1). J. Heterocycl. Chem. 1970, 7, 117-121.
7. Revankar, G.R.; Townsend, L.B. The synthesis and PMR study of certain 3-substituted 2-(â-D-ribofuranosyl)indazoles (1a). J. Heterocycl. Chem. 1970, 7, 1329-1332.
8. Alonso, G.; Garcia-Munoz, G.; Madronero, R. Heterocyclic N-glycosides. VII. Synthesis of 2-glycosylindazoles. J. Heterocycl. Chem. 1970, 7, 1435-1437.
9. Korbukh, I.A.; Blanco, F.F.; Preobrazhenskaja, M.N. 1-Glycosylindazoles. Tetrahedron Lett. 1973, 46, 4619-4622.
10. Kam, B.L.; Imbach, J.L. Nucleosides de synthese. VI. Sur l'identification definitive des ribofuranosyles de l'indazole. J. Carbohydr. Nucleosides Nucleotides 1974, 1 (3), 287-289.
11. Boryski, J. Transglycosylation of â-D-ribofuranosylindazoles. Nucleosides Nucleotides 1995, 14 (1 & 2), 77-89.
12. 1 synthesis, properties and biological activity of indazole nucleosides. Nucleosides Nucleotides 1989, 8 (4), 599-617.
13. Seela, F.; Bourgeois, W. Stereoselective synthesis of indazole 2′-deoxy-â-D-ribonucleosides: glycosylation of the nucleobase anion. Helv. Chim. Acta 1991, 74, 315-322.
14. Seela, F.; Jawalekar, A. 4-Nitroindazole: its ambiguous nature in oligonucleotide base pairing and the influence of the glycosylation position on the duplex stability. Helv. Chim. Acta 2002, 85, 1857-1868.
15. Brauniger, H.; Koine, A. Synthesis of 2-D-glucopyranosylindazole. Pharmazie 1965, 20 (7), 457.
16. Barascut, J.-L.; Kam, B.; Imbach, J.L. La réaction de fusion: examen systématique des facteurs influençant ia distribution des produits de ia réaction. Bull. Soc. Chim. Fr. 1976, 11, 1983-1988.
17. Preobrazhenskaya, M.N.; Korbukh, I.A.; Tolkachev, V.N.; Dobrynin, J.V.; Vornovitskaya, G.I. Les Colloques de l'INSERM (Nucleosides Nucleotides); INSERM; Marcel Dekker, 1978; Vol. 81, 85 pp.
18. Benchidmi, M.; Bouchet et, R.; Lazaro, P. Synthèse et réactivité de nitro indazoles. J. Heterocycl. Chem. 1979, 16, 1599-1603.
19. Stevens, J.D.; Ness, R.K.; Fletcher, H. Synthesis with partially benzylated sugars. XI. Studies on synthesis of the anomeric 5,6-dimethyl-1-D-ribofuranosylbenz-imidazoles (ribazoles). Comparison of the condensation of 2,3,5-tri-O-benzoyl-D-ribofuranosyl bromide and 2,3,5-tri-O-benzyl-D-ribofuranosyl chloride with 5,6-dimethylbenzimidazole. J. Org. Chem. 1968, 33 (5), 1806-1810.
20. 2-(â-D-ribonucleosides). Acta Crystallogr., C 2004, C59. (submitted).
21. Recondo, E.F.; Rinderknecht, H. Eine neue, einfache synthese des 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranosides. Helv. Chim. Acta 1959, 42, 1171-1173.
22. Zinner, H. Darstellung der β-tetraacetyl-ribofuranose. Chem. Ber. 1950, 83, 153.
23. Guthrie, R.D.; Smith, S.C. An improved preparation of 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose. Chem. Ind. (Lond.) 1968, 17, 547.