Synthesis of 4-substituted imidazo[4,5-d][1,2,3]triazine (2- azapurine)nucleosides

Nucleosides, Nucleotides and Nucleic Acids

Volumn 19, Issue 1-2, 2000, Pages 39-68

  Krawczyk, Steven ^a,b   Migawa, Michael T ^a,c   Drach, John C ^a   Townsend, Leroy B ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

^b GILEAD SCIENCES   (United States)

^c ISIS PHARMACEUTICALS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDRAZINO 7 (BETA DEXTRO RIBOFURANOSYL)IMIDAZO[4,5 D][1,2,3]TRIAZINE; 4 METHYLAMINO 7 (BETA DEXTRO RIBOFURANOSYL)IMIDAZO[4,5 D][1,2,3]TRIAZINE; 4 METHYLTHIO 7 (BETA DEXTRO RIBOFURANOSYL)IMIDAZO[4,5 D][1,2,3]TRIAZINE; 7 (BETA DEXTRO RIBOFURANOSYL) 4 (4 NITROBENZYLTHIO)IMIDAZO[4,5 D][1,2,3]TRIAZINE; 7 (BETA DEXTRO RIBOFURANOSYL)IMIDAZO[4,5 D][1,2,3]TRIAZINE; GANCICLOVIR; NUCLEOSIDE DERIVATIVE; TRIAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; CHEMICAL STRUCTURE; CYTOMEGALOVIRUS; CYTOTOXICITY; HUMAN; HUMAN CELL; METHODOLOGY; NONHUMAN; SYNTHESIS;

ANIMALIA; CYTOMEGALOVIRUS;

EID: 0034101229     PISSN: 15257770     EISSN: None     Source Type: Journal    
DOI: 10.1080/15257770008032996     Document Type: Article

References (23)

1. Bennett, L. L., Jr. Metabolism and Metabolic Effects of 2-Azahypoxanthine and 2-Azaadenosine. Biochem. Pharmacol. 1985, 34, 1293-1304.
2. Bennett, L. L., Jr.; Allan, P. W.; Carpenter, J. W.; Hill, D. L. Nucleosides of 2-Azapurines - Cytotoxicities and Activities as Substrates for Enzymes Metabolizing Purine Nucleosides. Biochem. Pharmacol. 1916, 25, 517-521.
3. Andres, J. I.; Herranz, R.; Lopez, M. T. G. Synthesis of 8-Methyl-2-azainosine and Related Nucleosides. J. Heterocycl. Chem. 1984, 21, 1221-1224.
4. Montgomery, J. A.; Laseter, A. G.; Shortnacy, A. T.; Clayton, S. J.; Thomas, H. J. Nucleosides of 2-Azapurines. 7H-Imidazo[4,5-d]1,2,3-triazines. 2. J Med. Chem. 1975, 18, 564-567.
5. Panzica, R. P.; Townsend, L. B. The Synthesis of 2-Azainosine and Related Derivatives by Ring Annulation of Imidazole Nucleosides. J. Heterocycl. Chem. 1972, 9, 623-628.
6. Kawana, M.; Ivanovics, G. A; Rousseau, R. J.; Robins, R. K. Azapurine Nucleosides. 3. Synthesis of 7-(β-D-Ribofuranosyl)imidazo[4,5-d]-v-triazin-4-one (2-Azainosine) and Related Derivatives. J. Med. Chem. 1972, 15, 841-843.
7. Montgomery, J. M.; Thomas, H. J. Nucleosides of 2-Azapurines and Certain Ring Analogs. J Med. Chem. 1972, 15, 182-187.
8. Bakulev, V. A.; Mokrushin, V. S.; Ofitserov, V. I.; Pushkareva, Z. V.; Grishakov, A. N. Synthesis of Analogs of 5(4)-Aminoimidazole-4(5)-carboxamide and Purines. 7. 7-(β-D-Ribofuranosyl)-4-methylthioimidazo[4,5-d][1,2,3]triazine. Khim. Geterotsikl Soedin. 1979, 6, 836-838.
9. Ofitserov, V. I.; Mokrushin, V. S.; Pushkareva, V.; Rapakova, Z. V. Synthesis and Properties of 4-Chloroimidazo[4,5-d][1,2,3]triazine. Khim. Geterotsikl. Soedin. 1974, 3, 428-429.
10. Ofitserov, V. I.; Pushkareva, Z. V.; Mokrushin, V. S.; Aglitskaya, K. V. Features of the Intramolecular Cyclization of 4(5)-Diazonio-5(4)-thiocarbamoylimidazolide. Khim. Geterotsikl. Soedin. 1973, 9, 1292.
11. Ofitserov, V.I.; Mokrushin, V.S.; Korbukh, I.A. Synthesis of 7-(β-D-ribofuranosyl)-4-methylthioimidazo[4,5-d]-v-triazine. Zh. Org. Khim. 1975, 11(4), 909-910.
12. a) Kelly, J. L.; Wilson, D. C.; Styles, V. L.; Soroko, F. E.; Cooper, B. R 7-(2-Fluorobenzyl)-4-(substituted)-7H-imidazo[4,5-d][1,2,3]triazines and 7H-pyrazolo[3,4-d][1,2,3]triazines. Synthesis and Anticonvulsant Activity. J Heterocyl. Chem. 1995, 32, 1417-1421.
13. b) Krawczyk, S. H.; Townsend, L. B. A novel synthesis of 2-Azaadenosine and Related Derivatives, 3rd Chemical Congress of North America, Division of Med. Chem., 1988, Abst. 19.
14. Adarniak, R. W.; Biala, E.; Skalski, B. New, Ionic Side-Products in Oligonucleotide Synthesis: Formation and Reactivity of Fluorescent N-/purin-6-yl/pyridinium Salts. Nucleic Acids Res. 1985, 13, 2989-3003.
15. Rodriguez, M. E.; Chern, J.-W.; Townsend, L. B. "Synthesis of a Potential Purine Nucleoside Phosphorylase Inhibitor 8-Amino-9-(β-D-arabinofuranosyl)guanine," 10th Int. Cong. Het Chem. Waterloo, Canada, Abstract P9-264. 1985.
16. Hofle, G.; Steglich, W.; Vorbruggen, H. 4-Dialkylaminopyridines as Highly Active Acylation Catalysts. Angew. Chem. Int. Ed. Engl. 1978, 17, 569-583.
17. Nelson, T. D.; Crouch, R. D. Selective Deprotection of Silyl Ethers. Synthesis 1996, 1031-1069.
18. Cava, M. P.; Levinson, M. I. Thionation Reactions of Lawesson's Reagents. Tetrahedron 1985, 41, 5061-5087.
19. Johnson, J. A., Jr.; Thomas, H. J.; Schaeffer, H. J. Synthesis of Potential Anticancer Agents XIII. Ribosides of 6-Substituted Purines. J. Am. Chem. Soc. 1958, 80, 699-702;
20. Still, W. C.; Kahn, M.; Mitra, A. Rapid Chromatographic Technique for Preparative Separations with Moderate Resolution. J. Org. Chem. 1978, 43, 2923-2925.
21. Shipman, C., Jr.; Smith, S. H.; Carlson, R. H.; Drach, J. C. Antiviral Activity of ArabinofuranoSyladenine and Arabinofuranosylhypoxanthine in Herpes Simplex Virus-Infected KB Cells. I. Selective Inhibition of Viral DNA Synthesis in Synchronized Suspension Cultures. Antimicrob. Agents Chemother. 1976, 9, 120-127.
22. Turk, S. R.; Shipman, C., Jr.; Nassiri, M. R.; Genzingler, G.; Krawczyk, S. H.; Townsend, L. B.; Drach, J. C. Pyrrolo[2,3-d]pyrimidine Nucleosides as Inhibitors of Human Cytomegalovirus, Antimicrob. Agents Chemotlier. 1987, 31, 544-550.
23. Prichard, M. N.; Turk, S. R.; Coleman, L. A.; Engelhardt, S. L.; Shipman, C., Jr.; Drach, J. C. A Microtiter Virus Yield Reduction Assay for the Evaluation of Antiviral Compounds Against Human Cytomegalovirus and Herpes Simplex Virus. J. Virol. Methods 1990, 28, 101-106.