Synthesis of N4-amino and N4-hydroxy derivatives of 5-azacytidine. A facile rearrangement of the N4-amino derivative to 5-(3-β-D-ribofuranosylureido)-1H-1,2,4-triazole

Collection of Czechoslovak Chemical Communications

Volumn 69, Issue 4, 2004, Pages 905-917

  Pískala, Alois ^a   Hanna, Naeem B ^a   Masojídková, Milena ^a   Fiedler, Pavel ^a   Votruba, Ivan ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

1,2,4 Triazoles; 1,3,5 Triazines; Antibacterial activity; Cleavage; Hydrazones; Nucleosides; Ureas

Indexed keywords

1 CYANO 1 HYDROXY 5 BETA DEXTRO RIBOFURANOSYLISOBIURET; 1 TRIAZOLECARBOXAMIDOTRIAZOLE; 4 HYDRAZINO BETA DEXTRO RIBOFURANOSYL 1,3,5 TRIAZIN 2(1H) ONE; 4 HYDROXYLAMINO 1 BETA DEXTRO RIBOFURANOSYL 1,3,5 TRIAZIN 2(1H) ONE; 4 HYDROXYLAMINO 1 METHYL 1,3,5 TRIAZIN 2(1H) ONE; 5 AMINO 1 CARBAMOYLTRIAZOLE; 5 AMINOTRIAZOLE; 5 RIBOSYLUREIDOTRIAZOLE; 5 UREIDOTRIAZOLE; ACID; ALKALI; AMINOTRIAZOLE; AZACITIDINE; BIURET; CYANIC ACID DERIVATIVE; CYANO(FORMYL)GUANIDINE; GUANIDINE DERIVATIVE; HYDRAZINE; HYDROXYLAMINE; METHANOL; METHOXY 1,3,5 TRIAZINONE; METHOXYRIBOSYLTRIAZINONE; RIBOSYLCARBAMATE; TRIAZINE DERIVATIVE; TRIAZOLE DERIVATIVE; TRIBENZOYLRIBOSYL ISOCYANATE; UNCLASSIFIED DRUG; WATER;

ANTIBACTERIAL ACTIVITY; ARTICLE; CHEMICAL REACTION; CYTOSTASIS; DRUG SYNTHESIS; HEATING; HYDROLYSIS; METHANOLYSIS; REACTION ANALYSIS; THERMODYNAMICS;

EID: 2442526619     PISSN: 00100765     EISSN: None     Source Type: Journal    
DOI: 10.1135/cccc20040905     Document Type: Article

References (19)

1. Pískala A., Šorm F.: Collect. Czech. Chem. Commun. 1964, 29, 2060.
2. Šorm F., Pískala A., Čihák A., Veselý J.: Experientia 1964, 20, 202.
3. Hanka L. J., Evans J. S., Mason D. J., Dietz A.: Antimicrob. Agents Chemother. 1966, 619.
4. Bergy M. E., Herr R. R.: Antimicrob. Agents Chemother. 1966, 625.
5. Hanna N. B., Masojídková M., Pískala A.: Collect. Czech. Chem. Commun. 1998, 63, 713.
6. Pískala A., Hanna N. B., Masojídková M., Otmar M., Fiedler P., Ubik K.: Collect. Czech. Chem. Commun. 2003, 68, 711.
7. Šorm F., Pískala A.: Ger. Offen. 1 922 702; Chem. Abstr. 1970, 72, 79427.
8. Kobe J., Stanovnik B., Tišler M.: Tetrahedron 1970, 26, 3357.
9. Allen C. F. H., Bell A.: Org. Synth. 1946, 26, 11.
10. Levin Ya. A., Kukhtin V. A.: Zh. Obshch. Khim. 1963, 33, 2673.
11. Taylor E. C., Hendess R. W.: J. Am. Chem. Soc. 1965, 87, 1980.
12. Pit'hová P., Pískala A., Pit'ha J., Šorm F.: Collect. Czech. Chem. Commun. 1965, 30, 2801.
13. Hirata T., Wood H. B., Driscoll J. S.: J. Chem. Soc., Perkin Trans. 1 1973, 1209.
14. Ukita T., Hamada A., Yoshida M.: Chem. Pharm. Bull. 1964, 12, 454.
15. Pískala A., Gut J.: Collect. Czech. Chem. Commun. 1963, 28, 1681.
16. Perrin D. D.: Aust. J. Chem. 1963, 16, 572.
17. Čihák A., Šorm F.: Collect. Czech. Chem. Commun. 1965, 30, 2091.
18. Recondo E. F., Rinderknecht H.: Helv. Chim. Acta 1959, 42, 1171.
19. Pískala A., Hanna N. B., Zajíček J., Čihák A.; Collect. Czech. Chem. Commun. 1989, 54, 2502.