Synthesis of some novel N-ribosyl-1,2,4-triazin-6(1H)-/ones or thiones as potential antibacterial and antifungal chemotherapeutics

Nucleosides, Nucleotides and Nucleic Acids

Volumn 24, Issue 2, 2005, Pages 111-120

  Khalil, Nasser S A M ^a  

^a Agricultural Research Center   (Egypt)

Author keywords

D Ribosyls; 1,2,4 Triazines; Antibacterial; Antifungal; Synthesis

Indexed keywords

1,2,4 TRIAZINE DERIVATIVE; 5 (4 CHLOROBENZYL) 3 PHENYL 1 (2,3,5 TRI O BENZOYL BETA DEXTRO RIBOFURANOSYL) 1,2,4 TRIAZIN 6(1H) ONE; 5 (4 CHLOROBENZYL) 3 PHENYL 1 (2,3,5 TRI O BENZOYL BETA DEXTRO RIBOFURANOSYL) 1,2,4 TRIAZINE 6(1H) THIONE; 5 (4 CHLOROBENZYL) 3 PHENYL 1 BETA DEXTRO RIBOFURANOSYL 1,2,4 TRIAZINE 6(1H) THIONE; 5 (4 METHOXYBENZYL) 3 PHENYL 1 (2,3,5 TRI O BENZOYL BETA DEXTRO RIBOFURANOSYL) 1,2,4 TRIAZIN 6(1H) ONE; 5 (4 METHOXYBENZYL) 3 PHENYL 1 (2,3,5 TRI O BENZOYL BETA DEXTRO RIBOFURANOSYL) 1,2,4 TRIAZINE 6(1H) THIONE; 5 (4 METHOXYBENZYL) 3 PHENYL 1 BETA DEXTRO RIBOFURANOSYL 1,2,4 TRIAZIN 6(1H) ONE; 5 (4 METHOXYBENZYL) 3 PHENYL 1 BETA DEXTRO RIBOFURANOSYL 1,2,4 TRIAZINE 6(1H) THIONE; 5 (4 METHYLBENZYL) 3 PHENYL 1 (2,3,5 TRI O BENZOYL BETA DEXTRO RIBOFURANOSYL) 1,2,4 TRIAZIN 6(1H) ONE; 5 (4 METHYLBENZYL) 3 PHENYL 1 (2,3,5 TRI O BENZOYL BETA DEXTRO RIBOFURANOSYL) 1,2,4 TRIAZINE 6(1H) THIONE; 5 (4 METHYLBENZYL) 3 PHENYL 1 BETA DEXTRO RIBOFURANOSYL 1,2,4 TRIAZIN 6(1H) ONE; 5 (4 METHYLBENZYL) 3 PHENYL 1 BETA DEXTRO RIBOFURANOSYL 1,2,4 TRIAZINE 6(1H) THIONE; 5 BENZYL 3 PHENYL 1 (2,3,5 TRI O BENZOYL BETA DEXTRO RIBOFURANOSYL) 1,2,4 TRIAZIN 6(1H) ONE; 5 BENZYL 3 PHENYL 1 (2,3,5 TRI O BENZOYL BETA DEXTRO RIBOFURANOSYL) 1,2,4 TRIAZINE 6(1H) THIONE; 5 BENZYL 3 PHENYL 1 BETA DEXTRO RIBOFURANOSYL 1,2,4 TRIAZIN 6(1H) ONE; 5 BENZYL 3 PHENYL 1 BETA DEXTRO RIBOFURANOSYL 1,2,4 TRIAZINE 6(1H) THIONE; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; DEBENZYLATION; DRUG STRUCTURE; DRUG SYNTHESIS;

ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; MOLECULAR STRUCTURE; RIBONUCLEOSIDES; THIONES; TRIAZINES;

EID: 15944369211     PISSN: 15257770     EISSN: None     Source Type: Journal    
DOI: 10.1081/NCN-200051902     Document Type: Article

References (20)

1. Niedballa, U.; Vorbrüggen, H. Pyrimidine nucleosides. Chem. Abstr. 1971, 74, 88267d.
2. Vorbrüggen, H.; Niedballa, U. Pyrimidine nucleosides. Chem. Abstr. 1971, 75, 20912a.
3. Vorbrüggen, H.; Kolb, K.; Niedballa, U.; Strehlke, P. Therapeutical 2-thio-6-azauridines. Chem. Abstr. 1971, 75, 49513g.
4. Niedballa, U.; Vorbrüggen, H. Pyrimidine nucleosides. Chem. Abstr. 1971, 74, 100361q.
5. Roy-Durman, P. Analogues of Nucleic Acid Components. Springer Verlag: Berlin, 1970; 42-45.
6. Beranek, J.; Sorm, F. Acyl derivatives of 6-azacytidine. Chem. Abstr. 1964, 61, 13405f.
7. Zabolotnyi, D.K. Institute of Microbiology. 6-Azacytidine. Chem. Abstr. 1965, 62, 13222h.
8. Restivo, A.R. Azauridines. Chem. Abstr. 1969, 70, 47807d.
9. Mansour, A.K.; Eid, M.M.; Khalil, N.S.A.M. Selective synthesis and reactions of 6-substituted-2-β-galactosyl-1,2,4-triazines of potential anticancer activity. Nucleosides Nucleotides Nucleic Acids 2003, 22 (1), 21-44.
10. Mansour, A.K.; Eid, M.M.; Khalil, N.S.A.M. Synthesis of some new 2-α-L-arabinopyranosyl-1,2,4-triazines of potential anticancer activity. Nucleosides Nucleotides Nucleic Acids 2003, 22 (9), 1805-1823.
11. Eid, M.M.; Abdel Hady, S.A.; Ali, H.A.W. Reaction of some 1,2,4-triazines with acetobromoglucose. Arch. Pharm. 1990, 323, 243-245.
12. Mansour, A.K.; Eid, M.M.; Khalil, N.S.A.M. Synthesis of some N-galactosides of 3-aryl-5-benzyl(or substituted benzyl)-1,2,4-triazin-6(1H)-/ ones or thiones of expected biological activity. Nucleosides Nucleotides Nucleic Acids 2003, 22 (9), 1825-1833.
13. Vorbrüggen, H.; Krolikiewicz, K.L.; Bennua, B. Nucleoside synthesis, XXII. Nucleoside synthesis with trimethylsilyl triflate and perchlorate as catalysts. Chem. Ber. 1981, 114, 1234-1255.
14. Vorbrüggen, H.; Strehlke, P. Synthesis of Hall's methyl 2-thiouridine-5-acetate from yeast-t-RNA. Angew. Chem., Int. Ed. 1969, 8 (12), 977-978.
15. Niedballa, U.; Vorbrüggen, H. A general synthesis of N-glycosides. I. Synthesis of pyrimidine nucleosides. J. Org. Chem. 1974, 39 (25), 3654-3660.
16. Al-Masoudi, N.A.; Pfleiderer, W. Synthesis and reactions of 6- and 7-p-chlorophenyllumazine nucleosides. Nucleosides Nucleotides 1989, 8 (8), 1485-1498.
17. Mansour, A.K.; Ibrahim, Y.A.; Khalil, N.S.A.M. Selective synthesis and structure of 6-arylvinyl-2- and 4-glucosyl-1,2,4-triazines of expected interesting biological activity. Nucleosides Nucleotides 1999, 18 (10), 2265-2283.
18. Khalil, N.S.A.M.; Mansour, K.; Eid, M.M. Synthesis of some novel 6-benzyl(or substituted benzyl)-2-β-D-glucopyranosyl-1,2,4-triazolo[4,3-b] [1,2,4]triazines as potential antimicrobial chemotherapeutics. Nucleosides Nucleotides Nucleic Acids 2004, 23 (12), 1889-1910.
19. Nalepa, K.; Bekarek, V.; Slouka, J. Reaction of azlactones with amino compounds. V. Synthesis and structure of 3,5-disubstituted-6-hydroxy-1,2,4- triazines. J. Pract Chem. 1972, 314 (5-6), 851-856.
20. Nalepa, K.; Slouka, J. Reaction of azlactones with amino compounds. I. Hydrazinolysis of unsaturated azlactones and cyclization of the hydrazides formed to give 1,2,4-triazine derivatives. Monatsh. Chem. 1967, 98 (2), 412-416.