Studies on some Azauracil Derivatives with Potential Biological Acti vities

Abstract

Stirring of 4-amino-3-mercapto-6-methyl-1,2,4-triazine-5-(4H)-thione (218) with dimethylsulfate in dimethylformamide in the presence of sodium carbonate at r.t. afforded the corresponding 3-mercapto-6-methyl-4-methylamino-4H-[1,2,4]triazine-5- thione (321) which on treatment with hydrazine hydrate in boiling methanol gave 3- hydrazino-6-methyl-4-methylamino-4H-[1,2,4]triazine-5-thione (322). Alternatively, treatment of 218 with methyl iodide in methanol in the presence of sodium methoxide at r.t. yielded the corresponding 4-amino-3-methylthio-6-methyl-1,2,4-triazine-5-(4H)­ thione (323) which on refluxing with hydrazine hydrate in methanol afforded 4- amino-3-hydrazino-6-methyl-4H-[1,2,4]triazine-5-thione (324).

s Me ll

N/NHMe

s Me \\

N/NHR

N'A

N'A

...--:::

'N SH

321 323

'N NHNH2

322, R=Me 324, R= H

Compound 322 was reacted with aldoses namely D-glucose, D-galactose, D- mannose, D-xylose, L-arabinose and/or D-ribose in refluxing methanol without any catalyst to yield 6-methyl-8-methylamino-3-(polyhydroxyalkyl)-2,8-dihydro-3H­ [1,2,4]triazolo[4,3-b] [1,2,4] triaz-ine-7-thiones (325a-t). Acetylation of the sugar derivatives 325 with acetic anhydride in pyridine at r.t. afforded the acetate derivatives 327a-f.