Abstract
Reaction of 6-aminoquinazolin-4(3H)-one (1) with a number of monosaccharides (2) in boiling methanol in the presence of a catalytic amount of glacial acetic acid afforded the corresponding N-glycosyl amines (3-6) in 65-70% yields. However, treatment of 1 with D-glucose in the presence of oxalic acid afforded Amadori rearrangement product 9 in 45% yield. Condensation of 2-aryl-3,1 -benzoxazin-4-one (10) with 4-amino-6-methyl-3-thioxo-1,2,4-triazin-5-one (11) in boiling acetic acid gave 2-aryl-3-[3-mercapto-6-methyl-5(4H)oxo-1,2,4-triazin-4-yl]quinazolin-4(3H)-ones (12) and (13) in 65% and 62% yields, respectively. Reduction of 2-(3-nitrophenyl)-3-[3mercapto-6-methyl-5(4H)oxo-1,2,4-triazin-4-yl]quinazolin-4(3H)-ones (13) using sodium sulfide in water gave the corresponding amino derivative 14 (in 61% yield), which was treated with 2 in methanol to give the corresponding N-glycosyl amines; (15-17) in 56-61% yields. The per-O-acetyl-beta-D-glycopyranosyl derivatives 7, 8, 18 and 19 were achieved in good yields by treating the corresponding N-glycosyl amines; 3, 4, 1 Sand 17, respectively, with acetic anhydride in the presence of pyridine. Anticancer evaluation of some of the prepared compounds have been tested, no compounds exhibited significant activities.