Synthesis, Characterization and Biological Activity of Some 1,2,4‐Triazine Derivatives.

Abstract

4-Amino-6-methyl-3-(2H)-thioxo-5-(4H)-oxo-1,2,4-triazine (1) was condensed with 2-methyl (or phenyl)-4H-3,1-benzoxazin-4-one (5a,b) in boiling acetic acid to give compounds 8-11. Reacting 1 with chloroacetyl chloride afforded the corresponding chloroacetamido and triazinothiadiazine derivatives 12 and 13. Condensing 2 with succinic anhydride and/or phthalic anhydride yielded compounds 14 and 15. Benzoylation of 4-amino-6-methyl-3-(2H)-thioxo-5-(4H)-oxo-2-(2,3,4,5-tetra-O-acetyl-α-D-glucopyranosyl)-1,2,4-triazine (19) afforded the corresponding 4-N,N-dibenzoyl derivative 20. Deblocking of the N-2 glycoside 21 and the S-glycoside 22 by methanolic ammonia gave compounds 23 and 24. Acetylation of 4-amino glycoside 25a afforded the corresponding 4-mono-and 4-diacetyl derivatives 26 and 27. Deamination of 25a,b yielded compounds 28a,b. Methylation of compound 28b afforded the corresponding N4-and S-methyl derivatives 29 and 30. J. Heterocyclic Chem., 42, 935 (2005).

5-Azacytosine Compounds In Medicinal Chemistry: Current Stage And Future Perspectives

“…Currently, special attention is paid to the investigation of an inhibitory activity of this compound towards monophosphate decarboxylase from the malariacausing parasite Plasmodium falciparum [69,70]. Synthesis and evaluation of diverse 1,2,4-triazine nucleosides as antiphlogistic, bacteriostatic [71] and potential anti-tumor agents [72,73] was also studied. Acyclic 1,2,4-triazine nucleoside analogues were prepared mostly within the search for new antiviral agents.…”

Synthesis, Characterization, and Antifungal Activity of Novel Benzo[4,5]imidazo[1,2-d][1,2,4]triazine Derivatives

“…Meanwhile, featuring a similar substructure, 3-phenyl-benzo[4,5]imidazo[2,1- b ][1,3,5]thiadiazin-4-one ( Figure 1 D) was also reported for its wide and potent antifungal activity [ 17 ]. In addition, the 1,2,4-triazine fragment, an important scaffold of some natural products, including toxoflavin ( Figure 1 E) and fervenulin ( Figure 1 F) [ 18 ], has been widely studied due to its promising bioactivities, such as antifungal [ 19 ], anti-HIV [ 20 ], antimicrobial, and anti-cancer [ 21 ] activities. Recently, the antifungal activities of 1,2,4-triazines derivatives against Candida albicans , Aspergillus niger , and Cryptococcus neoformans were found by chemists [ 22 ] .…”