Synthesis of Some New Nucleosides Derivatives of Possible Biological Activity

J. A. Hasanen*, E. I. Ibrahim, A. S. Orabi and M. F. Youssef

Chemistry Department, Faculty of Science, Suez Canal University, Ismailia, Egypt

Coupling of 2-methyl-4(1H)quinolinone (1) with a-acetobromo-sugers 2a-d in acetone under alkaline conditions afforded the corresponding N-glycosides 3a-d. Deacetylation of 3a-d with ammonia in methanol gave the deacetalyted derivatives 4a-d. Reaction of 4-Chloro-2-methylquinoline (5a) and 4, 6- Dichloro-2-methylquinoline (5b) with hydrazine hydrate in ethanol gave the corresponding 4-hydrazino-2-methylquinoline (6a) and 6-Chloro-4-hydrazino-2-methylquinoline (6b) respectively. Refluxing equimolar amounts of 5a and 5b with the respective sugar D(+) glucose (a), D(+) galactose (b), D(+) mannose (c), D(+) arabinose (d), D(+) xylose (e), D(-) ribose (f) and L (+) rhamnose (g) in ethanol containing 0.1 ml of catalytic acetic gave (4-quinolyl)hydrazones 7a-g and 8a-g respectively.

Synthesis; quinolinone; a-acetobromosugars; N-glycosides; (4-quinolyl) - hydrazones