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Synthesis of some novel N-glycosyl amines from aminoquinazolin-4(3H)-one derivatives

El-Brollosy, Nasser R., Abdel-Megeed, Mohamed F., Genady, Afaf R. and El-Hiti, Gamal A. 2003. Synthesis of some novel N-glycosyl amines from aminoquinazolin-4(3H)-one derivatives. Afinidad -Barcelona- 60 (504) , pp. 199-205.

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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-[3- mercapto-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-β-D-glycopyranosyl derivatives 7, 8, 18 and 19 were achieved in good yields by treating the corresponding N-glycosyl amines 3, 4, 15 and 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.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Dentistry
Subjects: Q Science > QD Chemistry
ISSN: 0001-9704
Last Modified: 19 Mar 2016 22:25

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