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‐glucopyra‐nosyl)‐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.

Synthesis and antibacterial activity of some new thiadiaza/triazaphospholes, thiadiaza/triaza/tetrazaphosphinines and thiadiaza/tetrazaphosphepines containing 1,2,4-triazinone moiety

“…Recently, significant activities have been directed toward this class of compounds, in particular, 4-amino-1,2,4-triazin-5(2H)-one derivatives which have considerable interest because of their herbicidal [6,7], antimicrobial [8][9][10], anti-HIV [11] and anticancer activities [12,13]. On the other hand, heterocyclic systems containing phosphorus atoms have considerable attention due to a large variety of interesting pharmacological and biological activities, such as herbicidal [14][15][16], insecticidal [17], antimicrobial [18] and anticancer properties [19].…”

Six‐Membered Heterocycles: Triazines, Tetrazines and Other Polyaza Systems

“…Several 1,2,4-triazines have been tested as analgesic and anti-inflammatory agents [198][199][200][201][202]. Significant activity towards leukemia, ovarian cancer and anti-HIV were observed in vitro for some 3,5,6-trisubstituted-1,2,4-triazines [203][204][205][206][207][208].…”

1,2,4-Triazine Chemistry Part II: Synthetic approaches for phosphorus containing 1,2,4-triazine derivatives

“…Recently, this class of compounds have gained considerable interest because of their herbicidal [7,8], antimicrobial [9][10][11], anti-HIV [12] and anticancer activities [13,14]. On the other hand, the high biological activity of organophosphorus compounds, such as highly active anti-TMV activity [15], herbicides [16,17], insecticides [18,19], antitumor [20] and war gases, is well known.…”